I recently watched the film Brad’s Status, a movie featuring Ben Stiller who plays Brad, a guy who’s constantly wondering if he’s on track in his career and life. There’s a scene in the movie, where Brad’s lying awake at night next to his wife who’s trying to sleep, and he’s stuck in a whirlwind of thoughts about whether he’s made the right career choices.
I love that scene because it so precisely reenacts the exact scene that’s played out in my own life, where I’m lying awake at night, staring at the ceiling, ruminating over things I probably shouldn’t be ruminating about when trying to fall asleep.
I’ve done a lot more of this self-reflection since starting my own business five years ago. It’s not that I didn’t reflect on things when I used to work full-time in the corporate world, but I just found that my day-to-day work-life used to be a bit more predefined. While I could make tweaks to the career path I was on, short of making a major career change, the trajectory was rather linear. The choices I made as an employee certainly had an impact on my team and projects, but enough checks and balances were in place within these large organizations to prevent any missteps from creating any long-lasting, significant damage.
On the flip side, it now feels like every decision I make about my business, every new client engagement I take on, and every new hire I bring onto my team has a much more profound and long-term impact on my work and well-being.
Here are four of the emotions I regularly experienced during my first years as a solopreneur that resulted in my fair share of sleepless nights.
Uncertainty
Back when I used to work full-time in the corporate world, although I never knew whether the company I worked for might announce a major restructuring or round of layoffs, I enjoyed a certain degree of stability. If I did my job well, I could expect a steady paycheck, cushy benefits, and even a nice bonus at the end of the fiscal year.
Running my own business has introduced a certain amount of ongoing uncertainty in my life. Not the kind of crippling uncertainty that punches me in my face every day, but a low-level hum that I always hear in the background. I often wonder what would happen if all my clients were to suddenly disappear. Or if all the organizations where I host workshops suddenly decided to no longer invest in the training I offer. While I think the risk of losing all my clients is low, the impact would be major.
The way I’ve dealt with uncertainty is to do what I can to diversify my offerings so I don’t have all my eggs in one basket. While I started my business doing 1-on-1 coaching, I now have a few different revenue streams from independent clients, speaking engagements, online courses, and podcast sponsorships. This helps me feel like I’m somewhat hedged against any sudden changes, although I still continue to think about ways to further diversify without losing my focus.
Confusion
I’ve always been a rather analytical person, and that side to my personality has served me well in the past, especially at organizations that valued rigorous analysis over gut-decisions. I myself tend to value logic over intuition, data over casual observations, and research over guessing. Taking a more left-brained approach to problems has helped me make rational business decisions in the past that tended to work out well.
In spite of this, I seem to have gotten a lot of things wrong since starting my own business, even after a lot of rigorous analysis. I’ve chosen the wrong platform for my website. I’ve chosen the wrong email marketing provider. I’ve hired the wrong freelancer to join my team. In each of these cases, I had to invest a lot of extra time and money into undoing my mistakes. These days, I sometimes doubt my decision-making abilities because I have gotten quite a few things wrong.
What I’ve started to realize is that I really need to trust my intuition more as a business owner, which has served as a more precise guide during my years as a solopreneur. I’m not sure why this is the case. Perhaps the world of entrepreneurship and freelancing is more nuanced. I’ve just found that my gut has tended to be correct more often than my analysis. Especially when it comes to deciding whether to work with a certain client or hire a specific freelancer, when something feels right to me, it tends to be right in the long run.
Doubt
When I was growing up, I used to love reading the Peanuts comic by Charles Schultz. The dichotomy between the Snoopy’s shameless confidence and Charlie Brown’s endless doubt is hard not to notice. I’ll always remember the comic strip where Charlie Brown says, “Sometimes I lie awake at night, and I ask, ‘Where have I gone wrong’. Then a voice says to me, ‘This is going to take more than one night.”
I don’t think of myself as an unconfident person per se, and I’d like to say that once I make a decision, I don’t look back. However, at times, I do look in the rear view mirror. At times, I do look to my side to see how I compare to others. And at times, I do wonder whether the path I’ve chosen is the right one for me in the long run.
My doubts these days range from wondering whether I left the corporate world at the right time to wondering if I’ll be able to grow my business as much as I want to wondering whether I will ever reach a point where I feel “successful” in what I do, especially now that the conventional milestones of promotions, end-of-year bonuses, and organizational recognition are gone.
Finding the right measuring stick to evaluate whether you’re on track is difficult. Sometimes looking toward other successful solopreneurs as a reference can be inspiring, but also depressing if you haven’t gained the same kind of traction as quickly with your own business.
To evaluate whether I’m on the right path, I try to focus on the important questions that matter, like whether I can do the things I want to do, whether I’m able to spend time with people who matter most to me, and whether I’m feeling 100% engaged with my work each and every day. Regrounding myself in what truly matters to me allows me to assess whether I’m broadly on track.
Excitement Continues To Fuel Me
This brings me to the final emotion, which is pure excitement. In spite of the fact that I feel my fair share of uncertainty, confusion, and doubt, I still wake up every single morning feeling really excited about the path I’m on.
In fact, excitement is also an emotion that keeps me up at night. Because I’m excited about all the work I do. I’m excited about the ideas I have about how to help more professionals pursue work they find more rewarding. I’m excited about the next podcast episode I’m about to release that might give someone in the world the push they need to take a brave step in their career.
I’m also excited about the life I’ve created for myself, doing meaningful work I find positive and fulfilling. A life where I have the flexibility to spend parts of my weekdays with my daughter and wife when I want. A life where I can work with clients remotely, without being bound to any physical desk. A life where I can control my schedule in a way that allows me to go for a swim in the middle of the day after I finish writing this article. A life where I can travel to spend time with people I care about without having to count vacation days.
Being a solopreneur has definitely resulted in me having more than my fair share of sleepless nights, but I actually think that you need a certain amount of productive paranoia as a business owner to stay afloat. And maybe that’s okay. Becuase when you’re doing work you enjoy and care deeply about, it has a ways of reenergizing you no matter how much sleep you’ve lost.
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This article was originally posted on Forbes.
