Episode 19: Work That Fits Your Life Now: 5 Flexible Ways to Earn in Your Next Chapter
In this episode, Brent and Rob dig into a question many people face in midlife: how to keep earning money while redesigning work to better fit who you are now. They explore the difference between productive stress and anxiety-driven stress, why so many of us get stuck in all-or-nothing thinking about careers, and what it really means to create a Second Act Paycheck that aligns with your life today. Along the way, they discuss flexible income paths—including consulting, freelancing, coaching, nonprofit work, and board member roles—and the identity shifts that often come with stepping away from traditional titles and routines. More than a list of options, this episode is about permission: to rethink work, question old assumptions, and take practical steps toward a next chapter that feels meaningful, sustainable, and true to you.
Links, resources, books mentioned:
Topics we are covering in this episode:
Why fulfillment, purpose, and income don’t have to come from full-time work
How all-or-nothing thinking around your next great act limits career options
Consulting as a common and flexible transition in midlife
Skill-based freelancing and gig work as a way to explore interests
The difference between consulting and coaching—and the mindset each requires
Why nonprofit and mission-driven work can offer meaningful rewards
The identity shift that comes with stepping away from traditional titles
Practical ways to explore your next chapter, including learning from people already doing the work
Transcript:
Transcript Disclaimer - May contain the occasional confusing, inaccurate, or unintentionally funny transcription moment. It’s all part of the show.
Lena: What if earning money in midlife came with more freedom, more choice, and a lot less pressure to do things the old way? Today on Midlife Circus, Brent and Rob talk about work that actually fits your life now. Not full retirement, not another soul crushing job, but flexible ways to stay engaged, challenged, and paid on your terms. From consulting and gig work to coaching and mission driven roles, this episode is about redesigning work for your next chapter. Before we begin, remember to follow Midlife Circus on Apple podcasts or wherever you listen, and join us in the Midlife Circus community on Substack.
Let's dive into work that fits your life now. Five flexible ways to earn in your next chapter.
Brent: Rob, when you imagine your next chapter, what's the first thing you know you don't want to do anymore?
Rob: Oh, boy. That's a big question, Brent. As I'm still trying to figure out pieces of it right now, I don't necessarily want to say one thing that I'm going to have to come back and eat those words to say I never want to do this again, and then I end up doing it. As you asked me that question, the first thing that popped into my mind is I don't want to work in a place where I'm personally stressed on a day in and day out basis. And I think about two different types of stress.
One is productive stress where there's intensity around the work where you're excited about doing something and it's actually a very productive thing to do, not the stress of anxiety. And I've talked about this before in terms of me exchanging stress for money while I was in my professional career. I know that I don't want to exchange stress for money anymore. I'll exchange joy with money. I'll exchange fun with money, but I'm not necessarily going to want to move into that same place I left where I was having significant stress on a day in and day out basis, which was all completely self imposed.
Had nothing to do with my prior employer, had nothing else to do. It was all about how I approached my work. And since leaving, I have had productive stress, especially around this podcast, making sure that we are providing great value. It's fun for you and I to do. It's good quality as we're doing it, but it's all been productive stress, something I very much look forward to every morning and not the negative stress where I wake up in the morning with anxiety about the day.
And I haven't had that since leaving my professional employment. To stress, one of my favorite movies, Office Space, I wouldn't say I've been missing it, Bob.
Brent: That's hilarious. I find that the way you describe that, the professional career often brings a lot of stress, but it's different types of stress. And I'm with you. I find that the stress that I usually had was self induced because I am a perfectionist by nature. So I'm always trying to do more, more, more, more, more, let's make it better, prettier, better, better, better, better, just stepping back and saying, is that the most important thing to be focused on right now?
And if it's causing stress or strain, why is it in being able to step back? But I find naturally in any organization, there's going to be stress because you're working with humans and humans introduce stress just on how we interact on a regular basis. But then there's that stress that's exciting as you described, and it's things that you look forward to because you're like, yeah, there are deadlines. Yeah, there are things that we're doing as you referenced the podcast. Yeah, we have deadlines.
We have kind of challenging ourselves to explore new topics and new ideas. And that's that creative stress that comes in because sometimes it doesn't come together the way that we want it to. But as we think about our next great act, and all of us are going to go through this at one point in time, and most often many times in our lifetime. But in midlife, when we think about our next great act, a lot of it comes back to career. What do I want to do?
So that's the main theme of today's conversation. And we call it the second act paycheck. And it's the work that fits your life now. So as we go into the conversation today, there's really two key takeaways we want the listeners to walk away with. The first is truly understanding that you don't need a full time job to feel useful, challenged, relevant.
So if you have the ability, you may change the way you work and it may be the amount of time you work. So that's one thing we'll talk about. The second is, is your next great act and how it should fit your life now, not the life that you had before. And I find that that's a little bit challenging for people because we may find, and for me personally, super challenge, is the life I had before, before I decided to go into my next great act was work sixty to eighty hours a week. And it was just be as full as possible.
Now I'm looking at it through a completely different lens and saying, yes, I still want to be productive. I still want to be active. I still want to be intellectually stimulated, but is there ways that I can do that that is just not crushing and creating the amount of stress that we started this conversation now? So a question that I have for you, Rob, as we go into our discussion today is, why do you think so many people think the only options when they're leaving the grind is full retirement or getting back into another full time role.
Rob: Before I answer that question, I got to take a step back though, Brent. You said humans cause stress, and working with humans cause stress. So working with you, I'm going to be completely straightforward with you, has caused me some stress. Alright? So, yes, I I could have done this all by myself.
Probably wouldn't have been as much fun, but it has caused me stress. The good news is it's been productive stress. I know I got to try and keep up with you, not let you down. It has been a positive thing. So, it's caused stress, but it has been productive stress.
Brent: I think I I think to my credit, I forewarned you did. When we went into this endeavor to say, hey, this is about the sixth time I've launched a business or a company, and there's this go button that I have, and it's hard for me to slow down. So I never want you to feel like you have to be on the same train as me every single day. But I know that sometimes I do cause stress because I'm always trying to, let's do this next thing. Let's do this next thing.
It's something I'm working on as well, so thanks for bringing light to that.
Rob: Alright. To go back to your question on and really that binary thinking, Brent, that you mentioned around either fully retired or back in a full time job. I think there's two pieces to that. One is we talked about in a previous episode, the retirement cliff. Right?
We've all been conditioned to, and this retirement is age 62, 65, whatever it is, and I'm retired, and that's it. And now it's the life of leisure. It's what all the imagery is around what retirement is and what that transition looks like. It's the thing that everybody looks forward to is that life of leisure at a later point in time in their life, and not necessarily fitting where we're at today in society and with our generation. That's the one piece of this, I think, is that, you know, we've been conditioned to think this is what retirement is.
And for some of us, leaving full time work, that's what we were comfortable doing. We were comfortable with the nine to five or as you and I had eight to eight, you know, full days, twelve hour days at times as we were working in leadership and in management and consulting. So it was something we left that was very comfortable when we got into the gap, and I know I experienced this, you've mentioned experienced this as well, is we got into that open space, and it became very uncomfortable. It became uncomfortable not to have something necessarily focused to do every single day. And so what is human nature when it's when it's in an uncomfortable place?
Human nature is to seek out comfort again. And how do I get to be comfortable? So this world that I'm in now where I don't have a lot going on is uncomfortable. Where was I at when I was really comfortable? Well, I was actually employed, and I was working for a company.
I was doing x, y, or z, and I'll go back to that to seek out place of comfort, not because somebody needs income. And I've worked with people that have retired from a very senior leadership role, never really needed to work again, and pretty quickly went back to work at a full time well, actually, more than full time work, sixty, seventy, eighty hour weeks right now. I know this person's working to try and help change an organization, and I think it's put him in a place of comfort. He is really comfortable in that environment and wants to stay in a place of comfort versus living in the discomfort around not having that calling, not having that thing to do every day. He didn't go find his next great act.
He went back to the great act that he had previously. What do you think are some of the reasons why the society has this binary thinking around retirement or which is full on life of leisure or I have to go back to work?
Brent: I think it's the way you described it is perfect. It's this comfort and it's what we know to do and it's what we know how to do. And that's challenging. It's hard to change behaviors. And we've had past episodes where we talk about habits.
If you have a habit and a routine every day to get up and do the same thing where you get up and you have your coffee, you might exercise, you go to work, and then you come home at a certain time and you have dinner and then you kind of wind down and then you start the whole thing over again after a good night's sleep. So if that is your habit, that is your routine, it's hard to break that. And it takes a significant amount of effort to do that. So the binary thinking comes in when somebody says, well, I really want to do something different. It's, I'm just maybe going to do it different in a different workplace.
Maybe that's the shift they make, but they create the same habits in that workplace, which may be the right step for them. Maybe that's the change they need. So I don't want to discredit that. We've talked to other episodes, we've talked about like health span. Is that amount of working seventy eight hours a week going to promote your overall longevity, your health?
Most likely not. I just think it's the DNA. I think we're so accustomed to the routine, but I also think there's societal pressure. Societal pressure comes in when people are trying to make a change and it's like, you're going to do what? You're going to go part time?
What? You're going to do something you actually want to do? Like, why would you do that? You're going to leave that big job in that big title. Why would you want to do that?
Because a lot of times when you're making change and you're really exploring your next great act, and we'll talk about this a little bit later in this conversation, is it requires you to think differently about yourself, about the way that you're viewed and stop really caring what other people think. That's a big part of it. So I think it's challenging. I've gone through it myself. I wouldn't say that I changed a 100% of my work habits, but I've changed some of the work intensity for me, meaning that it's not always on because that's something I've talked about quite a lot.
That's one of the things that I'm happy to leave behind is this always on mentality where go, go, go, go, go, go, go. I've changed that, but I've also taken a bigger interest in my own health. And that is the exercise and that is the diet. And that is really owning the sleep factor, which just makes the whole process that much better.
Rob: You talked about the, you know, people ask the question, what do you mean you're leaving this big senior role and what are you going to do with your time? Causes people to start thinking about it. And really the benefactor of that energy is actually the next employer. And the person I was thinking of actually left a really senior role at one firm, and the company that he's now with is going through pretty significant transitions that he's vital to the success of. And so he's driving a lot of initiative changes.
That next company is really benefiting from the work that he did. So he's getting positive accolades, and he's been promoted a number of times at the new firm. But the new company's winning, but there might be an unseen costing. That's what I really see as kind of that transition to that next thing that's almost identical to what he did before. Companies benefit.
Companies can actually significantly benefit from that transfer of information, knowledge, and skill set, but maybe at the cost of the individual, the individual's family, the individual's relationships or even the individual's health.
Brent: Yeah, absolutely. I mean, it's a big transition for everybody. So let's dive into some possible income paths. Because in prior episodes, we've talked about, we're seeing more and more from our listeners, our close friends, as they're listening to this podcast, they're saying, well, what could I do? Like, what should I do?
I know I need to make a change. I'm interested in making a change, but what are some possible pathways for me to explore that I could move into? We've identified five that most commonly hit us through our networks, our colleagues, our friends, and then we have a few honorable mentions. But I'm sure there are a lot more, so hit us up on Substack if there's any other ideas that we just blatantly missed, and our apologies if we did. But we're going to highlight five to start out possible income paths for your next great act that something to consider.
So I'll take the first one, Rob. And this is something that is near and dear to me because I've spent a big portion of my career doing is consulting. So consulting is something that people transition to often very comfortably when they go into their next great act. And consulting to me is described as you're really functioning in a specific area of an organization and you're bringing your expertise that you acquired throughout your career. So let's say you were in marketing and you were leading marketing teams and you've always been in the marketing space, you may become a consultant for organizations, bringing in your skillset, and you're bringing a skillset to them that they don't have.
So you're providing an offering that is consulted basis. It's very project based. That's an important distinction. Usually consulting work has a start point and a stop point. So it might be a three month engagement to help somebody launch a new product.
And I find why people in their next great act, especially in midlife like consulting is because it is project based, they can organize their life around the project so they don't have to be doing this 100% of the time. And they may be able to tap into their existing network to actually find the work. One of the cool things about consulting is if you go out to chat GPT or any of the large language models and you just ask, Hey, I'm considering doing some consulting projects. Can you share the billing rates that you would recommend for this? Can you share how I could scope this work?
You can get a lot of help doing that. And there's also other books out there that can help you with that. But I find consulting is an easy transition for people. If you've got a network and you've built up specific skills throughout your career that you can offer that can be of value for your clients. And I know Rob, maybe you could talk a little bit about this because this is something that you took on when you left your last company.
You've taken on some consulting assignments yourself.
Rob: I have. Yeah. And originally, Brent, I thought this was going to be a lot of the work and time and something I was going to invest a lot of time and actually money in getting up and running. And I spent a few months after leaving, you know, the grind to go and figure out what my next great act is, but this was always in the back of my mind. In fact, when I left the firm, I left the door completely wide open that I could go back and actually work.
If I got too scared or too uncomfortable, that door was wide open for me. But in the back of my mind, I had actually already started planting seeds for consulting, whether it be back to the prior firm or to other individuals. And as I got into it, as you mentioned, I'm doing some of that work today. As I got into it, I started thinking about how big can I make this consulting company? How many consultants would end up working for me?
How big is our span going to be? So I went through the process of creating a logo. I never got to the place of building website, but went through a lot of pieces about how to build out this business of doing consulting before I actually started doing any consulting. Before I started doing any of the work, I went big picture. How great can I make this thing, and what's it going to cost me to do that, and went down that path?
And then I started actually doing some of the consulting, which I actually love to do. I really love the clients I'm working with. It's been a lot of fun to be in the weeds in their business, helping them grow and transform their businesses. So I've loved that work. But what I quickly found out is the conflict between doing that work and the lifestyle I want to have.
So all the fun that my wife and I want to be able to go and do. To build out that big company, I would have been exchanging leaving the prior grind and prior business for this next big thing that I was going to go and build. That's that driver type a personality, make something big and super successful and make millions of dollars doing this consulting thing. I pretty quickly again realized that that's not the life I want to have today. I want to have the flexibility.
I want to have more control. I don't initially want to be in charge of other people as I start doing this work. And last week, in fact, I got the benefit of that because I've only taken on a couple consulting clients this year, and I probably only take on a couple at a time to be able to have that flexibility. But just last week, I did two consulting calls in the backseat of my van while Tara was driving down the highway to our next location to go and do something fun. If I had a full day of calls, that wouldn't work.
If I had calls throughout the week that wouldn't work, I couldn't have gone skiing at different locations, couldn't have gone on the hikes that I wanted to go on. And so for me, it's been about in the kind of the transition, it's what component of this business do I want to build? Do I want to build something big, or can I be really content being small, being kind of very niche in the approach and very selective in the clients that I work with?
Brent: I find the way you just described that is really, really important because I remember in the early days, I was probably one of the influencers behind this to say, do you want to build a bigger company? So you're not always doing the work. Because one of the challenges in consulting is you're only as good as the time you can put in and it can suck up your time. If you start taking more than two clients, that's usually the pressure point in any consulting engagements, a couple of clients more, it all of sudden becomes a full time job. And it does become stressful because you're trying to balance all the different needs of your clients and you want to deliver.
So there's these decisions you have to make if you go down the consulting path to say, what am I trying to accomplish? And I find if you do good work, you are going to find clients because that is the best, the referral business. So the way you described it is you're working with a few clients, they're going to reference you with colleagues in their network, and you're going to be able to reference the good work you're doing, and you'll find additional work, but it's also having the ability to say no. Or to say, I'd love to take you on, but my timeline is this, and maybe it's, I could start in three months because you know another engagement might be winding down. So I always look at it's a juggling act, but consulting can be very rewarding.
And I've been a consultant. I started consulting back in 1999 is when I started doing consulting. And then I built my own firm in 2001, and then I've had a lot of stops along the way. So I did consulting work and then I went back into industry, went back to consulting work. And so I've always had a flavor of that throughout my career.
And I find that really good consultants can create such a wonderful lifestyle as long as they're delivering quality product for their clients. And you can make a good run at it. You don't need to over complicate the consulting work. Recognize that it's going to be challenging for you if you're stepping out of some sort of industry or from a perspective, how do I get into this? The best place to start is typically within your network, within your own expertise, and really starting to send out emails to your close colleagues to say, this is what I'm doing.
Being very specific about what you're doing, not trying to be the Jack of all trades. That's one of the biggest mistakes consultants make at the very beginning is they believe I've had thirty years experience. I could pretty much do anything in an organization because I've done pretty much everything in an organization. That may be true, but that's a harder package to sell. Where you can sell in as consulting is a specific, I'm good at operations.
I'm good at supply chain. I'm good at strategy. As an example, I'm doing some strategy work right now and I love doing it for a client. Like I'm having a ton of fun and it's very specific. I didn't go in there to say I could solve all the challenges or address all the opportunities of this organization.
I narrowly focused it. And you end up being a better service provider, a better partner from them when you narrow your focus. I had a client once tell me, and this was at a really large financial institution. This was years ago when I was a consultant. And she came to me and it was my counterpart.
And she said, We love the work that you're doing, but I'm going to give you some feedback. And she said, You say yes too much to us. And I was so perplexed. I'm like, What do you mean? Like I say yes too much.
And she said, you're agreeing to all the possible work streams that we could bring you in, but that actually doesn't help us. Sometimes we need you to actually say, I don't think that's an important thing to focus on right now. Like give us pushback. And so that was a lesson learned for me.
Rob: You said good at something so I can do this. I'm good at this. I can do this activity. I'm good at that activity. That's one thing about our generation, Brent.
We're good at a lot of stuff because we had to figure out how to be good at a lot of stuff. Right? We couldn't be very niche in our approach. We had to actually be kind of jack of all trades to survive all the changes that we went through in our professional careers. Beyond being good at something, what I would suggest from a consulting standpoint is what's fun to you.
Right? So you could be good at a lot of things, but it may not be that much fun from a work standpoint. Or even more important, it may not be interesting. So if you have work that's fun or interesting that you want to do, that might be the best niche for you to work in rather than I'm good at this, all of these things. I'm glad you brought that up because we're all very versed in a lot of different areas.
What is the thing that's fun? What's the thing that's interesting to go and do?
Brent: That is so helpful. Because if you start to take on work that you're not excited about, your end product will be less than optimal. You won't deliver something meaningful to your clients because you're just doing the work, you're just going through the rhythm. So it's really important to, as you do your narrowing. So let's just kind of bring a closure to consulting is it's something I believe most people can do really well, especially in midlife because you've acquired so many skills and so many experiences.
So the first step is to really narrow it to what is your area that you want to target? Are you interested and excited about this area? And then tap into your network and be able to tell a story about how you can add value in that specific area. And then you can leverage different tools and resources to help you figure out how do you structure your engagements and your billing rates. And do you do something on a retainer?
Do you do something hourly? There's so many different ways to do it. Don't start there, start with your interest. What makes you excited? And then also understand, as Rob mentioned, if you start to take on lots of clients, it's going to be really intense and that may be what you want to do and that's okay.
But just recognize that the moment you hit that threshold of like three or four clients simultaneously, it's a lot. And I'm just speaking from experience, Rob, you're speaking from experience there as well.
Rob: All right, the next type of work, Brent, that we've talked about in the in the five key areas is gig work or, freelance type of work that somebody might go and do. And I would tell you to think about freelance or gig work as something that I would bet all of us did when we were a lot younger, and that's like babysitting or mowing all the neighbor's lawns. Right? It's only for a specific period of time, very short windows of time that you might go and do that activity, and it's not necessarily consistent work, if you will. It's only for brief windows.
So we did a lot of this when we got our podcast up and started, our business up and started, using freelancers to help us with this, whether it be graphic designers that helped us with our logo, a social media manager to help us get our social content up and running. We use a number of different freelancers to help us with this work. So freelance or gig work is for a set specific contract or project base. It could be an ongoing work or a very short term. It is different than consulting because you're just doing a task for an individual or for a company.
The other thing when I think about gig or freelance work you can do is you can also make up career pivot, I think, at this point too and actually go into something that you've never done before, but you find really a lot of joy in doing it and passion around doing it, and that is taking something that you did as a hobby before and you have passion around and transitioning that into a work that somebody might pay for. So here I think about photo editing or video editing or content creation. Those might be things from a standpoint where you can go in and help somebody because you have a skill set there you've been developing in your personal life that you're just like, you know what? I'm good at this. Maybe I can go and make a little bit of money on the side doing something I love, but only doing it occasionally so I don't quit loving it.
That's the downside of having some of these gig work. If it becomes too big and of something you love, you may actually not enjoy it as much anymore, and you may actually stop doing that thing as a hobby. Another way to think about gig work or freelance work, I would say, is recreational employment. And, again, it goes back to that seasonality or short windows. Recreational employment is taking something you love from a hobby standpoint, something out in the outdoors, a recreational habit that you might have.
So it might be, you know, ski instructing. It might be river raft guiding. It might be helping people on hiking trails and working for a hotel and a concierge being an outdoor adventure guide for individuals in your community. So there's a lot of types of recreational employment that people can go and do post leaving that big gig. It's the fun things to go and do.
And I mentioned, I think in our last episode, my sister and brother-in-law moved down to the Virgin Islands, and his gig work right now is he's a boat captain. So when he gets called, he goes out in a boat, spends all day on a boat in the ocean, driving people to go snorkeling or deep sea fishing, and he loves doing that every day. And it's not every day that he's doing that. It's every day he gets to go and do it because it's very sporadic type of work.
Brent: I find that the skills based freelancing is a really unique opportunity for people because you can explore so many different areas that are your curiosities, things that they never imagined they would be doing, but it's out there. But I'm also going to take it in a different direction as well, is when you get into specific gig work and we talked about the creative side. So if you're doing logo design or if you're doing, we used social media manager to launch the business or different services to help us with some of the aspects of our business. That is being challenged quite a bit right now with AI, those specific skills. So logo design, copyright editing, some of the social media creation, AI is really disrupting that space.
And also it's a very competitive space because you can tap into an international pool. So a lot of times, if you go into any of the common sites that could be like Fiverr or Upwork, you're competing against people from all over the globe. And some people might be able to charge $20 when you're like, I need to charge $200 So it's just one of those challenges that you have to navigate. I'm not discouraging it if you're going into a specific creative space as an example, go into it with eyes wide open, because it may be quite a barrier that you're trying to overcome because of the competitive nature, how AI is disrupting it, and it can just be challenging. So I don't want you to be let down because that's one of your passions.
But if it's passionate about it, I'm confident that you can find clients.
Rob: Absolutely. And some of the other areas, Brent, I spent some time in chat actually looking asking my chat to actually give me a list of all the freelancing gig type of work that's out there and like handyman. That's the person I'm going to hire. AI can't replace the handyman. YouTube can show me a view of how to fix something, which I've used a lot of times.
However, I'm not good at it. It takes me way longer than I want to, and I probably hire a handyman to do it instead of me. Not everything will get replaced, but I do agree with you. AI is going to have a pretty big impact on that industry overall.
Brent: I had a family friend growing up actually that he his next great act was he became a taxi cab driver. He liked having the conversations with people. He liked the flexibility he could have, and he earned a little bit money on the side. He just did it because it created social interaction. Alright.
Next one here. So we've talked about consulting. We've talked about skills based freelancing or gig work. The third one is coaching. And I hear this one a bunch, Rob.
And people say, I'd be a great coach. So let's define what a coach is. There's different types of coaches out there. Some of them are executive coaches where you might work specifically with the C suite, where you could work with CEOs, CFOs, COOs, and you're working with board of directors and you're coaching them. And then there's different types of coaches that might be coaching organizations through transitions.
And that might be a coach that is helping them with the change management aspect of a company that's merging with another. That's kind of reaching into the consulting space, but I wouldn't get too caught up in semantics here. Coaching is typically you're working with somebody one on one, or you might be working with a small team. And there is a timeframe, but it's much longer. Usually coaching engagements might be annual contracts.
And I have a close friend of mine is an executive coach and he's been doing this for, I think over twenty five years and he is exceptional at his craft. And he has some clients that he's been working with for that entire period of time. So he's kind of worked with those leaders and keep evolving the organizations. And they were once a startup and now they're a large organization. He's coached them all throughout that journey.
And I find that this is a place where people are very interested in and because they've got that specific experience of being an executive as an example, I just talked to somebody last week about this and he was interested about being a coach. And he said, I just want to share my knowledge, help future leaders avoid the pitfalls that I experienced. So that's a good starting place. Now I will challenge a lot of people that say, want to be a coach is just because you are a good leader doesn't necessarily mean that you're going to be a good coach. And I think, Rob, maybe you can relate to this because I know you've got coaching in your background, even going back several years when you were a ski coach.
What's the difference for you when somebody is a good practitioner at a certain thing, but then they may not be a good coach or they may be a good coach. What makes that transition successful or what possibly makes it fail?
Rob: The biggest thing, Brent, is it goes back to how you defined the difference between coach and consultant, I think. And one is, I think a consultant typically was a really good doer. They may have been leading a team and really good at doing different things and helping people do different things. A coach is helping somebody or a team be different. So it's not do something versus be different, where coaches are helping people evolve in their own personal skill set, get better at their craft, not do something better, but be better overall.
And, typically, they're going to deal with more than just the task. They're also going to deal with significant emotion in working with that individual as well as what are the emotional impact of the work. How do you coach them through emotional curves as a leader or as an executive? How do you help them show up better for their for their team and for their employees or for their organization? So I think it really contrasts the doing of the work versus the being better overall as a person, as an executive, as a leader.
Brent: That's a great distinction. I find as a consultant, you're hired to do something. You're either going to go build something, you're going to help them navigate something, but there is a start and a stop and it's a defined scope of work. When you get into coaching is here's the easiest thing for you to think about if you want to be a coach. You have to transition your thinking process to be a 75% listener and a 25% talker.
And usually coaching is set up that way. Consulting is the exact opposite. You're the doer and you're less listening because you're hired to come in and do something as a consultant versus as a coach, you're hired to listen and reflect and challenge. The best coaches I've ever worked with, and I've been really fortunate that I've worked with a handful of really good coaches in my career, is the ones that are great listeners. They hold me accountable to actually actions and put me to task, but they're not telling me how to do everything.
It's usually the great coaches are the ones that have me come up with that path and then they play it back and they really refine it and they really challenge. So I think it's a great place for people to go in their next great act. But I find that, and I'll use this because I've been around the space long enough. I find that most people that want to become a coach actually really want to become a consultant. And I find that a lot of people aren't wired to be a good coach.
It's just because you spent your career being a doer and you were just so good at your craft and you're so wired to just roll up your sleeves and just solve the problem versus coaching others to solve the problem. It's a big distinction, but it can be really rewarding work. And I know some great coaches. I've done some coaching work. I find that today I gravitate a little bit more towards coaching than consulting because I'm starting to understand how I can be better as a coach.
But if you would ask me ten years ago, I probably wouldn't have been a great coach because I was so accustomed to execution, to doing the work.
Rob: As we transition to the next topic, which is finding something that's rewarding, we're going to keep coming back to that theme on a regular basis as you think about what that next thing might be that you're going to go and do. From an income standpoint, the biggest thing is what are the rewards you're looking for? And this next category will likely have some of the largest emotional rewards. We're not maybe the most financial rewards, but some of the largest, I think, were emotional rewards in in your personal life, and that is actually working in non profit or mission based work. And I'm not talking about volunteering.
That's something that we've talked about before. It's something that Brent, you and I both do. This is actually working in a non profit and actually taking the skill set from your employment career and helping a non profit grow. Typically, they're not going to be able to pay you the same level of what you did when you left the organization. You may not need to work as nearly as many hours for that nonprofit, but you're taking that skill set as something that made you really successful in your career, and you're transferring that to an organization that desperately needs that level of help to get to the next level or to continue to provide the impact that they're having in the local community.
So it's a really deep option. I know you and I know a couple of people that have gone in and taken employment at nonprofit organizations find great joy every day in doing that work. They do find some frustration, though, because they want to see change because they're so emotionally tied to what that organization is doing. So the pain is, I wish we could go just do more, and they get frustrated by that piece of it, but they find great joy in the impact they're having on either their local community or on a national level, and the rewards of doing that work are just huge.
Brent: And I find that most people that do this, if they can successfully make that transition from the income is going to be different and the pace is most likely going to be different, it doesn't mean that nonprofits don't want to do more. It means that there's typically a limitation associated with what they can do because of the funding. It's just a practicality. But if you can get in there and say, you know what, I was really good at coordinating people or doing project management. Maybe I can go help this nonprofit with some of their events.
And it may be a paid position. It may not pay what you used to get, but it could be really rewarding. And also you may love the work and it may be a little bit more flexible for time. That's a huge win. Maybe that's the win you're getting out is you still get that intellectual stimulation, but then you're also getting the flexibility in your schedule that you would like at this stage in your life.
So I think this is a great area. I know in our community that we live in the mountains of Colorado, there's hundreds of nonprofits. And if you go to most communities throughout the country, if not the world, there's a ton of nonprofits. It's not hard to look up and just see which ones are doing what. You can see open positions.
I mean, there's a lot of great opportunities out there. So it's one that we encourage people to explore. If you're looking for that mission driven work, it might be really, really rewarding for you.
Rob: Might start volunteering with that organization a little bit just to get into the inner workings, but I do believe that actually working at a nonprofit has significantly more impact than just the volunteering work that you can actually have there because you're helping that entity change and grow and get to their potential.
Brent: Absolutely. All right, so this next one of our five possible income paths is board member or strategic advisor. So now this is very niche focused and I just want to put that caveat out there, but I know a lot of people that are pursuing being a board member. And for me, I've been on several boards in my career. And I want to say that this is a viable pathway for a lot of people.
It takes a ton of patience, but it's also very similar to that coaching consulting dilemma that people have. Just because you are a great operator doesn't mean you're going to be a great board member. So let me just break it down for you. As a board member, you're typically in a for profit company. It can be a paid position.
It's usually paid with both cash and some sort of equity if it's a private and a publicly traded company. And you have specific assignments when you're on a board. You have four board meetings, typically that's the standard every year, but then there's committee meetings and then there's some carve outs sometimes for specific functions or projects that are specific to board member leadership that you can assign yourself to or volunteer in. All of that is part of the roles that you could play as a board member. Here's the great thing about being a board member is it keeps you at an elevation if you like that elevation, meaning you're working with the C suite typically, and you're working on strategy and the direction of the organization.
So if that's the type of work you like, and you've got experience doing that, it may be very rewarding for you. The challenge that most people face when they want to become a board member is they're not patient, meaning board positions just don't show up all the time. And so you have to be patient for finding opportunities. And then once you're in it, you have to be understanding of your role as a board member. That elevation is really important.
If you go in there with the expectation of that you're just going to start doing a bunch of the work, then you need to actually go find that job. Because board members are typically not the doers, they're actually more like a coach. I've been on private company boards, I've been publicly traded company boards, I've also been on non profit boards and they all have different characteristics, different expectations. So I find that the work can be rewarding. If you're interested in that type of work, if you just go out and do some searches, they're actually companies that are set up to help find board positions.
And so they work with a lot of large organizations, small organizations, and it's more of a placement agent. It's like a recruiting company. Those services are out there. But I find because I've done it, it can be incredibly rewarding work. But I also want people to be very practical with this one.
It's not fit for everyone. You want to make sure that your experience is aligned with typically that industry that you may go serve as a board member and that you are operating at the right level in your career that you could see yourself as a board member and your peers could see yourself as a board member. So we put it in here because Rob and I hear people say that quite a bit and they also ask us, what do you think about becoming a board member? So we just wanted to share that. Any other observations from your side, Rob?
Rob: A couple of thoughts, and then I have a couple of questions for you. So as you mentioned, there are agencies out there that will help you find board positions, whether it be paid or unpaid positions on boards. I also when I left, I started getting emails from those recruiting firms asking me if I was interested in being on a board. So they reached out directly to me on LinkedIn saying we have services to help you find board positions. So there are a number of opportunities that for you to help find a board if this is something that you want to go and do.
My question for you, Brent, though, having been on a bunch of boards, and I've never done that before. You mentioned for profit and nonprofit type of boards. You mentioned publicly traded and non-publicly traded boards. Publicly traded, non-publicly traded typically have pretty significant income streams that may come with those board member positions, but I think a lot of people seek out really significant income from being on a board. What are some of the roles that their boards are going to be looking for?
What are some of the history or the experience a board might look for in a really high level candidate for a high level board position?
Brent: That's a great question. So typically you're going to bring in your skillset. And so your skillset, if you were known for sales and you're in a specific industry, then you may be able to help them unlock new opportunities, open up doors, and you can bring in your expertise, but at an elevation as a board member. So you might be able to partner with the head of sales within that organization, just to share ideas with them and set the strategy for that specific function in the organizations. It often has to do with the industry you came in.
So let's say for you, Rob, you came from financial services, most likely you're going to be attractive to companies that are financial services specific to the work that you were doing because they know you've seen a lot of things and you can add value to the overall direction to that organization. So it's typically industry is kind of a starting point for board members. And the second thing is your specific expertise within that industry is typically what those recruiting agencies are going to look for is to say, could Rob actually add value from an industry perspective, but then his specific skill sets of maybe the last ten or fifteen years of his career, is that something that can help further advance that organization if he were to serve in a board member capacity? And then that's on the publicly traded privately held. I want to be clear, most nonprofits are non paying.
That's just something that aligns to volunteering work, but it still has the same level of intensity as a board member when you're on a nonprofit board. So let's just be clear that I wouldn't put out the expectation that you're going to get paid if you're working on a nonprofit board. I don't know if I've ever seen that before. I'm sure it's out there, but that usually creates a conflict because that's that defeats the purpose of being a nonprofit.
Rob: Two more questions for you, Brent, on this topic. One would be, do you need to be a C level executive to be on a paid board?
Brent: No, not at all. Okay. Not at all. I think it has a lot to do with your expertise and industry knowledge. So a gentleman I talked to last week, he's founded a bunch of small companies and he's kind of exploring his next great act and he probably could sit on a fair number of boards in his specific area of expertise.
Rob: Okay. My last question on this topic is, you mentioned recruiting firms or headhunters, for lack of a better phrase, might reach out to you or you can reach out to them to find board positions. If somebody is interested in being on a board besides, you know, waiting or reaching out to a a company to help them find a position, what are some of the other things they could do right now to become a more viable board member candidate?
Brent: So the first thing is make sure your LinkedIn is very up to date. And it's also representative. You're not misleading, but it's representative of leadership. It's not representative of all the micro tasks that you may have done, but it's strategy, it's change, it's how you navigated complexity. So it's representing more of leadership attributes versus tactical attributes.
And then to me is start conversations with your network of people that have a board of directors and ask them, how do they use the board of directors? And what do they look for in their board? Cause every board's going to be a little bit different from a dynamics perspective. And I always say there's kind of two types of boards. There's the board that they're helping the company operationally navigate what they're working on.
And that is people that kind of roll up their sleeves a little bit. And then there's strategic boards that are always focused three to five years out. And those are the two big attributes. But to your question is update your resume to reflect leadership and then start conversations with people in your network or even reaching out to people outside of your network to understand how they're using boards. What do they look for in board members to make sure that you could be a possible fit for the companies in the future.
Rob: Great, thanks.
Brent: Okay. So we've talked about the big five that we come across quite a bit. That's consulting, that's gig work or freelancing work, coaching, nonprofit mission driven work, and board member strategic advisor, that type of work. Now there's a few honorable mentions that we'll do more of a lightning round. The first one is teaching and facilitating.
We see that where people are doing adjunct professional roles at like community colleges, they're leading workshops, they're guest lectures, facilitating retreats. The next one is creator IP based work. So that's something similar to what we're doing right now. Launch a podcast. We also do writing within the podcast, like our monthly newsletter comes out on Substack, speaking courses, things like that.
That's more creator type work. Some people really want to focus on becoming an investor and that might be investing in small companies or funds, doing direct deals. That's something that we see on a regular basis. And then there's another one that we've learned about, but we don't know a ton about, but it's Workaway style experiences. I know that some people are trying to do short term assignments in maybe another country.
So there's different companies that help facilitate that. And that's something if you're curious about travel, you might be able to integrate that in. So those are few of the honorable mentions, but we just wanted to share that in the broader theme of when you're exploring your next act paycheck, these are some ideas that come to the surface. So Rob, we've given a few ideas, but one of the biggest challenges that I find people have in making a shift into their next great act is the identity shift. And it's really what's happening in midlife.
And we talked a little bit about it before. How do you approach this? Because we now have something to do with your title's going to be completely different. Your status may be completely different. You used to be the one, the person that was leading the organization or leading that function, and now you may not.
So how do you help people navigate that identity shift?
Rob: I think that's one of the biggest reasons, Brent, of the binary thinking about going back to work full time and going back into the same industry, even the same company, has to do with mindset around their own personal identity. So I was the VP in this and that, or I was the national director of this, and that step in that change might be to a assistant director or a just a worker type of role or no title at all unless you give it to yourself because you started your own company. And that can be tough for some people to negotiate, you know, leaving that six figure income, and if that's where they were at, to making, you know, less than that, significantly less than that. And the thing I would say is really think about what's important to you now. And is the title as important as your happiness and your health, your enjoyment, your family, your relationships, all of those things.
And your title isn't going to go on your gravestone unless you really make a big impact about what your job is and you think that that's your key identity. It's what do you want to be known for, and what were they going to write on your tombstone. So that's what I would suggest people do as they think about fit and the identity shift in terms of leaving a big role and going to something likely significantly smaller as to why you're making that transition in the first place and what's most important to you. And Brennan mentioned flexibility. As you think about flexibility, why is that so important?
Why does that fit in? I think right smack hand in hand with identity shift.
Brent: Absolutely, and that is the gain. So a lot of people get too fixated on, I'm losing this title. I'm losing this status. I might be losing a portion of my income. I understand all those things can be important at one point in time in your life.
And I don't want to undermine the importance of income if that's important to you at this stage and that's something you need to do. But my challenge back to our listeners is what are you gaining? And you may gain flexibility that you've been craving. You may gain purpose that you've been craving. So there's a lot of things that you have to balance these things out.
It's not going to be a perfect fit. It's a really tough transition if you're trying to do a one to one replacement. It can be much more beneficial and much more rewarding when you think of the bigger picture. Yeah, I might be losing a few of these things, but I might be gaining all of these things. And that could be the win that you're looking for.
So as we wrap up the conversation today, Rob, is we hear it every day in the work that we're doing with Midlife Circus. One of the things that people commonly share is they feel so overwhelmed with all of these options. And it's the, I could do list. I went through it where I had my 18 items that I want to do. What's one small step that people can take to start to move forward?
And I'm saying a step that they could take, let's say in the next thirty days to feel like you're making progress on your next great act.
Rob: You said this already, Brent, and as you were talking about board positions, it's reach out to someone that's in that world already. So if you have this list of ideas of things you might want to go and do where you might get excited, reach out to the person that's already doing it. Reach out to someone that's had that experience and ask them questions. Ask them what their experience is. We're really talking about trying to find the fit in this next world, and that person who's doing it will likely give you the best assessment whether or not it's going to be a fit for you.
So understanding the non-negotiables are different for every person. It might be flexibility. It might be income because you might need to have some form of income to supplement your retirement or this transition. It could be that you want to have more impact. You want to have fun.
You want to have be physical. You want to have ownership. Right? What are your non-negotiables first and foremost? And then talk to somebody who's already doing the activity to give you insight as to whether or not it's going to be a good fit for you.
Brent: And that's exactly it. The whole idea of this conversation is you have permission to go explore your next great act. Give yourself that permission, Start to explore it, start to talk to people. That's great advice, Rob. Talk to somebody that maybe is in a position that you're curious about.
Somebody in your network that is a consultant and they've made that transition and how did it go for them? What did they learn? A lot of times when you do that, you may find work in doing that because they're like, Oh, you're considering doing this? Well, if you decide to do something, I have a few projects that I'd love to have you join me on. I've seen that happen.
So get curious about it, start having conversations. And remember, as you go through this, think about what you're going to gain. And this isn't a binary type I really, really encourage people to think a little bit broader is I need this one to one replacement. Think about it a little bit broader and challenge yourself to say, how could I get this flexibility? How could I find the work that I'm truly enjoying or that I find that I'll have much more purpose and I feel like I'm getting something out of and I'm sharing my gifts to the world.
So those are the challenges that we want to put out there. So Rob, one of the things that we like to do and one of our favorite things as we close out our conversation today is listener feedback, whether it's comments, ideas for us. So you had one that came recently that I'd love for you to share because I think there's some fun humor in it as well.
Rob: It was pretty funny that we got in direct feedback. So this goes back to our episode where I mentioned that getting that daily cup of coffee at the fancy coffee place for it's the triple pump extra whip non fat extra fat mocha frappa whatever chino thing it is, and the impact of that on personal choice, right, or on personal life, and that that coffee every day is the same price as an annual international trip. And we had a listener actually give me their exact order. Liz gave me her exact order of what she gets every time. And I'm not saying don't do it.
Just be conscious of the fact you're doing it. And so I got the exact order of what she gets every single time she goes to the one of these fancy coffee places. It's only a singular one she wanted to make sure she reminded me of. It's only one coffee place she'll ever go to. And we had another listener actually chime in, and I got to read this word for word, Brent, because it was pretty funny.
And the comment was, it's funny how boomers get triggered about coffee. I know we get caught quite often confused with being boomers. Really clear, we're not boomers, but it is funny how we as Gen Xers do get triggered about coffee.
Brent: It's something that's very important to a lot of people. So as we close out today, thanks for listening. And remember, you are the director of your next great act.
Lena: That's it for this episode of Midlife Circus. Visit midlifecircus.fm for show notes, transcripts, and all the latest happenings. And be sure to join us in the Midlife Circus community on Substack. Follow Midlife Circus on Apple podcasts, YouTube, and wherever you get your podcasts so you never miss your next great act. Quick reminder, the opinions and stories shared here are personal reflections, not professional advice.
This show is for entertainment and inspiration only. Thanks for listening, and we'll see you under the big top next time. Midlife Circus is a Burning Matches Media production.