The Whole Picture

Last week I came across a post about being tired of "entrepreneurship thirst traps." It was an excellent post that was really inquisitive versus negative and basically she was asking for the real truth, not the glorified social media angle. I connected with the author of the post and we had a good conversation but I haven’t been to stop thinking about the post.

Much like most things on social media, entrepreneurship tends to get pushed to one extreme or the other. It's either the greatest thing ever or the worst way to live anyone could choose but my experience had been neither and both.

I kept wondering though, had I unintentionally become someone who was only sharing the great things about entrepreneurship as a way to validate my own decisions and insecurities?

After a lot of thought, I landed on yes, I had avoided telling the whole picture behind entrepreneurship for the same reason most of us do anything, being vulnerable isn’t comfortable.

This October will mark 2 years since I went full-time in my business and almost five years since I started it. During that time, I've also had the opportunity to work with 40+ founders, and while every business is different, I've realized many of the emotions are exactly the same.

My entrepreneurial journey started in 2022, like a lot of people, I started it on the side while working full-time. It was a thrill to start something of my own, it was a new level of power to be paid directly by someone, and I realized how passionate I had become about the work.

There was also the identity challenge that exists when you have your main profession and then starting something on the side. You get questioned, you get judged, there are people who aren’t very supportive of this decision and aren’t afraid to let you know. All the while you are trying to build something with the little bit of time and energy you have that gives you options for the future.

Looking back, the biggest mistake I made those first couple of years was treating it more like a hobby than a potential career. I enjoyed it, I loved working with clients, but I wasn't fully committed to building the business part and it was because I was financially comfortable, I didn’t need to do the uncomfortable actions.

Then life sped up and changed rapidly in 2024, we had Cooper, I resigned my role, moved from Tampa to Richmond, and went full time on the business. I had an incredible contract opportunity that allowed the business to be financially viable from the start but also covered up a lot of the warts that I had ignored because again, I didn’t need to do the uncomfortable.

Then in October 2025 my first true entrepreneurial test came to fruition, the contract was not renewed and I was starring at a significant financial hurdle. I wasn't really worried about me or the business, I knew I'd figure something out one way or another.

What I was thinking about was having the conversation with Jenna, the person who believed in me the most and telling her one of our biggest sources of income was gone. That was the part I dreaded because it was the first time along this journey that I felt like I had completely failed our family.

Within 2 hours I knew exactly the path I wanted to go down next, I didn’t hesitate on wanting to continue moving forward with the business and knew that I wanted to actually see if my business vision from 2022 could be fulfilled. I had been thinking about this business model since day 1 but truthfully didn’t have the courage to move forward with it until I was pushed.

Jenna and I sat down and talked through my plan, I needed sober eyes to tell me if it was possible or not, she was steadfast, which having a partner who supports and believes in you even when you don’t isn’t just a nice to have it, it is the most important part of the entrepreneurial journey. We knew it would take time to build out this model, we knew it would eat into savings more than we’d want, but we also knew it had the potential to be something really incredible, so we moved forward.

I’d love to tell you that since that day I have been 100% confident each day but I have probably 2nd guessed myself about 150 times. I have updated my resume, looked at contract roles, questioned if I was actually crazy for taking on this type of risk for my family.

Then I got a piece of advice from a colleague that really changed my mindset around where I was headed, I shared with her that I was giving it until June and then reviewing the progress, that seemed like the responsible thing to do with a family in my mind. She challenged that thought, shared that it might just be the very thing that holding me back and had been holding me back. I needed to burn the boats.

My mindset has changed since then, I won’t sit here and try and tell you there haven’t been days where I questioned it all, but they have been far less. The wild part, and I have found this to be true for most people, is I don’t question myself when things aren’t going well but rather when they are, which is a fascinating part of the journey I didn’t know to expect, but see it all the time in other founders now.

Financially the business has grown faster than I anticipated but when I rebuilt it I opted for a reoccurring revenue model through many clients versus just a few so that a singular decision couldn’t rock the business. While long term it is the model that I want and believe in, it also has a growth curve and I am only about 75% of where I was last year which brings in the biggest hurdle of all.

We knew we were going to use savings to offset the business build and objectively it is the right choice for our family long term but objectively and emotionally are way different. Each month when I see the savings balance go down I find myself mentally calculating exactly how much time I have left and you think about the number that was in the account 6 months ago and want to be sick.

As I think through the journey thus far I don't think I am afraid of failing, I am afraid that I will have made a selfish decision. That I was asking for my family to give to much, that I wouldn’t make it for them, not me.

Those are the headliners but then there are the other not so glamorous parts. Health insurance is far more complicated than I imagined it would be and cutting the check every month versus it coming out of your check hits way different. I am my own tech team which isn’t good because there are weeks where I spend more time figuring out a printer than coaching. While you have time freedom, you sometimes find yourself wasting an incredible amount of time and avoiding the important without anyone keeping you accountable. Finally, there are days where you flat out don’t feel like doing the necessary work and you can choose to skip it in that day but the impact is noticeable in the income statement the next month.

I've worked with founders building businesses far larger than mine, and I've realized the doubts don't magically disappear at a certain revenue number, the limiting beliefs don't disappear, the uncertainty doesn't disappear. Typically it just doesn’t last as long and doesn’t cripple quite as much. It becomes a hit that you take and you keep moving, that is what I believe separates those who make it who do not make it.

Reading this it probably sounds like entrepreneurship has been incredibly difficult and it has been but it is only part of the journey.

Every afternoon I'm home when Cooper gets home from school. During his first 2 years, we were able to keep him home instead of putting him in daycare. There have been afternoons at the park at 2pm and Fridays at the golf course. I've built a business around the life I wanted instead of trying to fit my life around my work.

As a family we get to take trips without asking permission for time off, I am able to prioritize my hobbies and health without taking time away from my family, I rarely have something on my calendar that I don’t want to do and while I am not always the best boss to myself, I am the best boss I’ve ever had.

Professionally I get to spend my days helping founders build businesses that fit the life they actually want and truly love the people I work with and get to help. The challenges that I mentioned have made me better and more valuable to my clients as I can understand exactly where they are mentally when something good or bad happens.

Entrepreneurship has been one of the hardest things I've ever done. It's also been one of the best decisions I've ever made, both can be true.

I think we owe people the whole picture of what entrepreneurship actually looks like, the good, the bad, the uncertainty, the freedom, and everything in between and that starts with me.

My hope is that this inspires you to share your whole picture as well.

Hit reply and tell me this: What's one part of your entrepreneurial journey you don't normally share because it's uncomfortable?

I'd genuinely love to hear the whole picture.

Paul