Entrepreneurship Is An Endurance Sport - EP 005

pleasure & profits podcast Nov 30, 2023


If you’ve ever felt like, “I should be working harder,” or “I should be getting there faster,” or “This entrepreneur stuff is really freaking hard. Maybe I’m just not cut out for it,”...then this episode is for you. 

Today I’m sharing my experiences in marathon training, transitioning to long distance cycling, the insights and mental challenges inherent in both disciplines, and how they translate to the world of entrepreneurship. 

We’ll dive into the commitment to push through the discomfort and also how to know when to call it quits. Because what brings you pleasure & profits might be challenging. It might be hard work. But in the end, it should absolutely bring you satisfaction.

Tune in as I share with you: 

  • A personal story of training for my first (and only) marathon and how that mental game was much like entrepreneurship
  • How the longest and best bike ride I’ve ever done was one I didn’t finish, and why that was a good thing
  • How you get to choose your goals, pace and direction as an entrepreneur, but whatever you choose, it’s always an endurance sport
  • The importance of setting a sustainable pace in business to have the impact you want to have in the long term
  • How pleasure is found in the experience of the challenge, not in winning the race

Satisfaction as a strategy isn’t for everyone, but if you are passionate about making a difference in the world, you’re excited about the work you do and how it can impact people’s lives, and you love to challenge yourself, then it might be for you, if you choose it.



  • Endurance is a key quality for entrepreneurs, and it is important to set a sustainable pace.
  • Finding pleasure in the journey and enjoying the process is crucial for long-term success.
  • Entrepreneurs have the freedom to choose their own path and set their own goals.
  • Pleasure and feeling good are not something to be earned in the future, but our birthright in the present.
  • Creating a fulfilling and successful life is possible by choosing joy and satisfaction in our work.


If you’re ready to have a deeper conversation about how to maximize impact, profit and pleasure in your business and life, you can schedule a time to connect with me right here >>>

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Episode Transcript

Hello and welcome to Pleasure and Profits. Thank you so much for being here. This is episode number five, and I'm so thrilled to share that the feedback so far has been so, so good. And I am beyond excited about some of the guests that I have coming up for you in future episodes. So stick around, tell your friends because it's going to keep getting better and better. 

Today, I want to share a story with you, or I guess a couple of stories really, that I hope will resonate and feel relatable to anyone who's listening, who's an entrepreneur, who is passionate about their work in the world, who is hardworking and committed, and who sometimes looks around at what other people are doing and feels like, I should be working harder, or I should be getting there faster, or this is really freaking hard, maybe I'm not cut out for this at all. So if you've ever felt that way, then this episode is definitely for you. 

It all started with this guy that I met on Tinder who said, 'The thing to remember when it comes to endurance sports is that no matter how good it feels or how bad it feels at any moment, you can be sure it's gonna change.'

This was in 2016, and that guy from Tinder was my then brand new boyfriend, now husband, Rocky. And he said those words to me in the early weeks of training for my very first and only marathon. I was 38 at the time, and one day in June or July, I said to my sister Jessica, let's run a marathon together. And for some reason, she agreed. The plan was she would train at her home in Florida and I would train in Texas, and we would run the Rock and Roll Marathon together in San Antonio in December. This was not my first stab at marathon training. I had started training for one once, like maybe 12 years earlier, but due to an injury, I had to ease off the miles, and I ended up racing the half instead. So the farthest I'd ever run at that point was 16 miles. Rocky, on the other hand, was a veteran of the endurance world.

Not only had he run a marathon, but he was an iron man and had been racing bikes for over a decade. He knew what he was talking about. As the weeks passed and my training progressed, to my surprise, I found myself eagerly anticipating my Saturday long runs. In fact, I would build my entire weekend around them. I'd go to bed early on Friday night. I'd wake up at 6: 30 on Saturday, practice my pre-race routine, stretching, coffee, toast with peanut butter, PRD, then I'd get in the miles, and then I'd head back home for an ice bath, some food, a long nap, and somewhere around 6 p.m., I'd re-enter the world of the living, usually to go eat tacos and drink bourbon with my newfound love. It got to me that my short runs were the ones that felt really tedious. I couldn't really get into a groove in just a few miles.

One time my sister and I were lamenting, much to her husband's annoyance, how we didn't even feel warmed up until five miles in. (cue eye roll) 

In contrast, I loved the long runs. Once I passed that 16-mile marker, every distance I did was the farthest I'd ever run. I craved those Saturday morning runs. Each was an hours-long project to tackle, with a clear objective that could be measured in minutes and seconds. They were also incredibly painful. Every time I extended my distance, those last couple of miles would feel like pure torture. 14-mile run, the last two miles were torture. 16-mile run, last two miles were torture. 18-mile run, yep, the last two miles were torture. I'm talking like every single step was a shot of pain through every inch of my feet, up through my calves, into my quads.

And I wasn't injured. I wasn't like running on shin splints or something. It was just really, really uncomfortable. My feet were tired. My legs were tired. My body ached. Those last two miles were 100% a head game every single time. Can you keep going even though it hurts? Will you keep going even though it hurts? I could do anything for two miles, I would tell myself, and I would do it.

And every Saturday I'd get out there and I'd do it again and again and again. I had a goal. I knew it wasn't going to be easy to get there and I was willing to do the work. But I wasn't a masochist. I wasn't like a win-at-all-cost kind of person and I'm even less so now. I did push myself, but I knew my limits, sort of. If I felt like I needed extra recovery time, I would shave off a training day and run four instead of five.

When  after  a  different  kind  of  marathon,  one  full  of  work  events  that  had  me  running  in  a  Brooklyn  cemetery  early  mornings  one  week  before  heading  off  to  one  conference  center  and  then  headed  to  Atlanta  or  another  conference the next week, I decided that racing around a hotel conference room for three days straight in high heels would have to suffice for training purposes and I bailed on my runs altogether.

Looking back now, I can see that I pushed myself hard, but not too hard. It felt good. I was excited about it and I was up for the challenge. The day of the race, the temperature was in the low 50s and it was raining. So over 26 miles and for four and a half hours, my sister and I would get rained on, we would dry out, we'd get rained on again and again and again.

There were stretches in that time that we talked and talked, and I pointed out all of the San Antonio sites. We got a photo in front of the Alamo. There were stretches of mutually agreed silent time. At about 14 miles in, we started taking 30-second walk breaks every two miles at the water stations, and we stayed side by side the entire time.

And Rocky was right. There were times I felt great and there were times I felt like total shit. And the one thing that was for certain was that those feelings would change and then they would change again and they would change again. The last few miles, we were both hurting. I could feel the strain, but I was on an adrenaline high and just mentally coaching myself through it. I could do anything for four miles, I told myself. I could do anything for three miles. I could do anything for two miles.

And I know Jess was hurting too, I could feel it. I did my best to coach her on as I coached myself and we just kept moving. As we turned the final corner and set eyes on the finish line about 100 yards away, I will never forget this moment. Out of the blue, she says, "'I'll race you' and takes off sprinting." It took me just a split second to react and there was no freaking way I was gonna let her beat me to the finish line.

So we sprinted to the finish line. We crossed it together with people cheering us on, “go girls!” Officially, I beat her by a tenth of a second. And Rocky was there at the finish line with flowers for both of us. As I said, this is my first and only marathon. Jess, on the other hand, went on to run five more in five years, including New York City and Boston, and shaved an entire hour off of her time.

I opted to pick up cycling and in a matter of a few years worked my way up from 15 mile rides to 50 to 100 and beyond. And the same experience held true through all of them. Sometimes I'd start out with a bitter cold biting me in the face, my legs, my fingers, hating every minute of it. And an hour later, I'd be loving life, enjoying the sun and the wind in my hair. And an hour after that, my hamstrings would be burning and my back would be aching and I'd be counting down the miles.

On the bike, the mantra became, I could do anything for eight miles. Those last eight miles were a killer every single time.

Of course, both of these activities are physical challenges, but mostly they're a head game. Can you make it through the lows, the pain, the discomfort to get to the part that feels really good? Can you make it the last eight miles to your goal? Are you going to quit when it inevitably starts to feel like shit because it will? Are you going to make the best of it? Are you going to find the things to appreciate in the moment? Are you going to complain about how hard it is the whole way there?

Sometimes you can and do, and sometimes you choose not to. I entered one mountain bike race in my first year riding. I was so naive I had no idea what I was getting myself into. I was strong and fast-ish, but I had no skills for the technical terrain at all. So five miles into an eight-mile race, I started to burn out. Had muscled my way through as much as I could, and I just didn't have anything left in me.

I fell and I fell and I fell again and again and again. I lost all the tools off my bike somewhere on the track and I pushed on. But by mile seven, mile eight, I was alone in the woods struggling to keep moving forward at all. I remember thinking, ‘fuck this bike race.’ As an entrepreneur, my entire life is me alone in the woods trying to survive. I do not need to do this shit in my free time, and I never entered a mountain bike race again. 

As an entrepreneur, you get to pick the game. You get to set the goals, you get to pick the distance, and you get to pick the pace. You get to decide when to push on, when to rest, when to walk away from a choice, a commitment, or the whole damn thing. You get to pick the game, but whatever one you pick, you can be sure that it's an endurance sport. 

And unlike sprints, it's not about how fast you are out of the gate. It's about setting a pace you can hold for the long haul. That doesn't mean you don't speed on the downhills and you don't grind it out on the uphills. It means you hold the pace that fits the circumstances, and it's a pace that you can keep up for a long, long time. It's about enjoying the highs along the way, and it's about how well you've trained your mind to keep going even when it gets difficult.

It’s about knowing what your goals are and being willing to do the work to get to them. It's also about knowing that your goals might change, and that's okay too. The best and longest ride I've ever done was a race that I didn't finish. 165 miles into a 210-mile bike race on gravel roads after 13 hours on the bike that included ankle deep mud, miles of sand, blazing sun, and some major digestive distress. Having started at 6.30 a.m., Rocky and I sat looking at each other at 10 p.m., trying to decide if we were going to finish the final 45-mile leg of this race that we'd not only trained extensively for, but had driven from Texas to Michigan to do. My younger sibling, who had come along to be our support team, had met us at each of the checkpoints with food, water, and our little rescue pup, sat watching us.

Rocky looked at me and said, ‘if you want to finish, I'm in.’ And I, taking a swig off the Corona I was drinking because I knew I needed calories but I couldn't keep food down, I said, ‘if you want to finish, I'm in.’ And I meant it. I don't remember which one of us was smart enough to call it quits, but I do remember Rocky saying, ‘I got what I came for. An awesome day with you on the bike. We don't need to risk injuring ourselves just to get over the finish line.’

I was asleep in the car before we were out of the parking lot. So if you've been following me for a while, you might be wondering, how does all of this endurance talk fit with the idea of pleasure that I keep talking about? So let me explain. When I talk about pleasure, along with impact and profit, as a necessary component of a satisfying and sustainable business strategy, I'm not talking about so many of the things that the predominant culture associates with that word. Things like laziness, gluttony, selfishness, frivolity, or something sexual. 

Remember, pleasure is, by definition, a feeling of happy satisfaction or enjoyment. What brings you those feelings might be lounging around, indulging, luxuriating, daydreaming, I hope that those things bring you pleasure and I hope that you get to enjoy them as part of your lived experience. But what brings you pleasure might also be hard work. In fact, I'd be willing to bet that if you're listening to this podcast, you probably get substantial feelings of happy satisfaction and enjoyment, AKA pleasure, from doing your work in the world. In the same way, I ran that marathon and I entered into bike races, along with hundreds, sometimes thousands of other people.

We were not all there to win the race. In fact, most of us weren't even there to compete with the other participants. 99% of us signed up to the challenge for ourselves, to test ourselves, to improve ourselves, to do the best that we can do, or just to have fun. Because there's satisfaction in the challenge, and there's pleasure in the experience of it. So when I talk about satisfaction strategy, I'm not talking about, I'm not talking to people who want to sit on a beach and only work four hours a week, or not at all. This approach is for people who are passionate about making a difference in the world. They're excited about the work that they do and how they can impact people's lives. They love to learn and push and challenge themselves and they've proven their grit by building something, a career or a business venture and becoming an expert along the way. 

What they long to master now, what I think you long to master now, is how to do the work in a way that allows for the quality of life and richness of experiences that you desire. And the way to do that is to tune in to what feels good and what feels aligned. That does not mean it will be without effort, but that the effort will feel inspired and satisfying. 

This isn't the path for everyone. Most people in the world, entrepreneurs or not, will work happily or unhappily for decades to build something that they'll get to enjoy someday. And if that's what you wanna do, then by all means do that. There is of course the risk that someday never comes. 

What I propose is that pleasure and feeling good are our birthright, not something we have to earn and enjoy at some distant future time. I believe that we can create beautiful, joyful, prosperous, and impactful lives now. All we have to do is choose it, commit to the challenge, understand that this is an endurance sport, that no matter how good it feels or how bad it feels in any moment, you can be sure it's gonna change.

And that we're here for the pleasure of the experience not to win the race. And so until next time, I'm wishing you even more pleasure and profits and I will see you soon.

More Impact, Profit & Pleasure Awaits...


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