The Trail So Far: Reflections after a Decade in Business

For most of my life, my dad was an entrepreneur. Along with a business partner, he owned and operated a screen printing and embroidery business for over 20 years until they sold it a few years ago. My exposure to this entrepreneurial career path (along with a strong dislike of being told what to do) is largely what led me to becoming an entrepreneur.

When I was in my third year of business and feeling like I was flailing around, I asked my dad when he felt like he had “made it” in his business - when he was able to stop worrying if the business would fail or that he would have enough revenue. 

His response - the ten year mark.

My dad explained that this was when the relationships he built over the years provided him with word-of-mouth marketing and new customers without additional effort on his part, his business processes had no more kinks, and his revenue was consistently what was expected (not that it was consistent each month but that there was a seasonal pattern that could be relied on year after year).

Since August 2026 marks ten years of my own business, it’s a great time to pause and reflect on my experience of building a business. Before we dive into reflection, let me give you a little backstory on how I got here.

2016 - graduated with my doctorate and began working as a 1099 contracted worker for another private practice

2017 - left that 1099 contract, opened the physical doors to my own practice (clinical and mental performance), and created my own contracted position with a local university (all mental performance)

**Important note: I borrowed $15,000 from my parents to cover the upfront cost of buying assessment materials which I paid back over the first three years.

2018 - had my first kid and took a maternity leave

2020 - had a second kid, the COVID pandemic hit, and I shifted to mostly online work

2021 - created an online mental skills course (had minimal sales)

2022 - kids came home full-time to begin homeschooling

2023 - launched Project E with Abby

2025 - took a contract with a team (not a good fit and it ended early)

2026 - ended previous contract with local university; created a testing program with a specialized dyslexic school and am working as a consultant for them

At multiple times over these ten years I’ve also had health issues to deal with: surgeries, shingles, miscarriages, migraines, and chronic pain.

There were two things that jumped out at me when reflecting on these ten years and actually listing out what happened. First, while my dad’s business became more similar and consistent year after year, mine hasn’t had a repeatable year yet! Second, I wouldn’t say that I feel like I’ve “made it.” While I do certainly know that being an entrepreneur is the path for me and one I will continue for many years to come, there remains a lot of uncertainty as to what each year will bring and how exactly the journey will unfold. 

Rather than speaking as an expert, someone who has “been there, done that,” I want to share as a fellow entrepreneur on this journey. Below I’ve listed out three lessons I’ve learned over these ten years of business, as well as three lessons I’m currently re-learning. Becoming an entrepreneur is about building a business that fits your life. These lessons reflect how my business fits my life and what values I prioritize as I continue along the journey. This is not meant to be prescriptive. However, I truly believe that the more examples you see of successful entrepreneurs, the better you’ll be able to craft the best business for your life.

What I’ve learned:

Take time off around the holidays.

In the first few years, I often took any work that came my way as I simply needed to be paid. As a result, I frequently said yes to adjusting my schedule to accommodate the needs of clients. In particular, for my psychoeducational evaluations, this included working over breaks when students would be out of school - spring break, fall break, winter break, summer break.

While on one hand it was nice to be able to offer a service that worked well for my clients, I found myself resenting the schedule I created and dreading going to work, especially around Thanksgiving and Christmas. Now, I have a hard rule that I block off time for the holidays. For me, that includes: my birthday, my immediate family’s birthdays, Thanksgiving, Christmas, and New Years.

Being an entrepreneur means you’re in control of your schedule, so make it one that works for you.

Entrepreneurship is a wicked environment.

There are many people who will purport a “right” way to do things:

“Follow this four-step framework to get fully booked with clients.”

“Here are the three strategies that close the deal.”

“Tired of hustling for new clients? Get the Easy Client Playbook.”

While there are things that might make it more likely for me to get the outcomes I want, it’s not as straightforward as many will claim. In David Epstein’s book, Range, he explained the difference between a “kind” environment and a “wicked” environment. In a “kind” environment, there is a clear outcome with an accurate, cause-effect feedback loop. Take golf - there is a clear objective for a specific shot and after the shot, the player gets immediate and accurate feedback related to that shot and outcome. If a golfer steps up to a putt and sinks it, the feedback is that they assessed the green well and provided the right amount of speed and power in their putt. If they missed it, the feedback is also clear: if they were short, not enough speed; if the shot was off left or right, their assessment of the green was off. In these “kind” environments, adjustments can be made with a strong assumption on the impact of the overall outcome.

In contrast, “wicked” environments have problems that are more nuanced with a greater degree of uncertainty. Additionally, feedback for those outcomes is often inaccurate, unavailable, or delayed. Entrepreneurship is a wicked environment. Running a successful business is impacted by components that vary largely from individual to individual. Add to that the inability to rely on the feedback loop - the new client I got today may be a result of me talking to someone yesterday, because of me doing a workshop three months ago, or because my old teammate from high school is now a coach and is asking for help with an athlete on their team. We don’t always know.

Being an entrepreneur in our field means accepting that there are so many things beyond our control and that you can do a lot of things “right” and still not get the success you are aiming for in the long run - and choosing to continue anyways. 

Instead of finding the right contract, create it.

Contracts are great! They can provide financial stability, offer a consistent connection with a team or organization, and generate referrals beyond the contract itself. One thing about contracts, though - they vary enormously. Some of the components of a contract that may be different include: the structure of what services are provided, the associated fees, the length of the contract (short-term, long-term, or ongoing), the time commitment required, who has access to the provided services or information, and the responsibilities of each party in the contract.

Over my ten years of entrepreneurship, I have never “found” a contract. There was no “opening” or “looking for a contractor” that I came across and responded to with a resume. Instead, every single one of my contracts were nonexistent until I built them from scratch. I developed a relationship with an individual and then generated an idea of a contracted position that enabled me to use my unique skill set to address a problem that I saw. 

I created what was involved, what I was willing to do, and how I wanted to be paid. While I did make some mistakes in crafting contracts - charged too little, worked too much, provided too much availability - I also completely owned what went into those contracts. I never had to be the “square peg in the round hole,” I just had to get better at creating the right size square hole for me.

Being an entrepreneur means creating contracts instead of finding them. The best contracts are the ones that you create to support the relationships that you develop.

What I’m currently re-learning:

Staying small is okay.

Many business books will push the idea that if your business is not growing, it’s dying. It is this constant pushing to become more and bigger that drives a lot of small businesses to become big corporations. I have felt this push time and time again: Take on more clients. Work an extra day. Bring on another person. Add on a contract.

There is nothing inherently wrong with growing and building a business to be bigger. However, for me, a bigger business does not equate to a better life. And if I’m an entrepreneur, shouldn’t my business promote the life I want to live rather than get in the way of it?

My anchor here that I am coming back to is: staying small is okay. A purposefully small business allows me to: 

• Have enough finances to have the necessities and luxuries I value

• Have time to spend with my family (and not work more than is absolutely necessary)

• Keep doing the parts of business I love (working with clients) and minimizing the things I dislike (managing employees)

• Ensure that my life is supported by my business, not run by it

Want to dive deeper into this concept? Check out the book Company of One by Paul Jarvis.

Embrace uncertainty.

For the past few years, I’ve held onto a myth that I will “have it all figured out” at some point (I know… stop laughing at me). Due to some pretty big and glaring experiences in the past few years, I am again faced with the need to accept that the future is unknowable. Yes, I can prepare to some extent and have plans for possible scenarios, but to have certainty about what will happen or how my life will unfold is preposterous.

Instead, I’m leaning into this anchor: embrace uncertainty.

I’m not talking about giving up on trying. This isn’t throwing caution to the wind “YOLO” style or releasing responsibility by saying “what happens happens.” Rather, embracing uncertainty is recognizing that I can only do the next right thing, not the next 50 things. It’s also trusting that I’ll be able to figure out what step comes next once I get there. It’s less trust in a predictable future and more trust in my ability to handle it - whether it’s something wonderful or challenging.

As an entrepreneur, the path isn’t laid out for us - we are constantly building it as we go. At times, this has been exhilarating; in other times, like now, it’s a touch more terrifying. In re-learning to embrace uncertainty, I am allowing the path forward to unfold while continuing to live life in the midst of the unknown. I’m doing what I can, pausing when I need to, and reminding myself to trust that, when it comes down to it, I’ll find a way to be okay.

Good for you, not for me.

The comparison trap is real. It’s so easy to see what others are up to: online, at conferences, and in social media. The version in my head of every other mental performance business is that they are financially stable and have all of the clientele they want. When I do see what others are doing, it doesn’t take much for me to slip into the stream of doubt - Should I be doing that? Do I need to offer that service? Maybe I’m not really doing this right.

Yes, even ten years in I still have doubts. It typically comes in waves and sometimes I am better at riding it than others. Because of the wicked environment, it’s easy for me to lack confidence in my ability to have a successful business. Not because I’m not working hard enough, but simply because sometimes (read: most times) I have no true control over the outcome. (All of my clients are smirking and pointing me back to my own controllables–uncontrollables lesson).

Lately, I’ve been coming back to my anchor - good for you, not for me. 

There are a lot of good ways to do business and life. Not all of them are a great fit for me. If you are big into social media and put out lots of content, good for you! Social media is just not for me. If you are heavily involved in committees and the Association for Applied Sport Psychology in general, that’s awesome and vital for our field’s success! I have two kids that we homeschool so my time is already taken up with something valuable to me. This anchor helps pull me back from that comparison ledge by reminding me that something can be good, even great, but not be a fit for me right now.

Doubt is okay. Ride the wave. There’s no one “right” way to do life or business. 

On that note, what a ride these ten years have been! So far, this entrepreneur journey has been awesome and challenging and exhausting and fulfilling. There have been ups and downs, crazy wins and distressing failures, and more curves than I ever could have anticipated. No, I’m not sure what will happen over the next ten years, but I’m sure to learn and re-learn many lessons along the way as I continue to take it one step at a time.