Last year, I said goodbye to the corporate/startup world and started my own business. For years I planned to launch an executive coaching firm and I decided the time had finally come. I was excited. I was nervous. I was confident in my plan. But I had a lot to figure out. There were many unknowns. 

I recently hit the one-year mark of running my coaching business and was asked by a friend how the experience has differed from my expectations. In an effort to answer their question, and document lessons from the past twelve months, I have written this summary. 

Here are the 17 lessons I’ve learned from starting my own business. 

1) I picked a bad time to launch a coaching business

At least that’s what everyone told me. A few months before launch, I started telling friends and family my intentions. At the time, the financial markets were softening and investment in tech/startups had come to a screeching halt. My target market included CEOs, founders, and leaders in the technology space. 

I was told companies would cut spending on leadership development. I was told that investment in coaching would be curtailed. They told me I should wait until the markets bounced back. I took their recommendations and chose to move forward anyway. They were right. It was a bad time to get started. 

2) I picked a perfect time to launch a coaching business 

While they were correct in many ways, the timing was perfect for me. I’d spent years building a coaching business on the side. I’d developed a system that delivered results. I actually planned to launch the business two years prior but decided the timing wasn’t right. I wasn’t ready yet. 

I’m glad I was patient. Those two extra years of preparation made a world of difference. I took an executive role at a startup and developed additional skills. When I made the leap, I was confident the time was right for me and my family. I was ready to go all in. I’m sure the tech slowdown made things more challenging, but I was able to have a great first year regardless. 

3) I love the autonomy and flexibility 

Every job comes with its own unique set of challenges. Being an exec coach is really hard. I have to show up 100% for my clients. I have to bring my all every time. It can be mentally and emotionally taxing. But it’s a job I love doing. The more freedom you have to solve problems you find interesting, the more satisfaction you’ll have in your career. 

Since starting my business, I’ve had more freedom to attend events and activities for my kids. I’ve also had more flexibility to exercise and read. This is a luxury. 

Having said all of that, I work as hard as I ever had. Maybe even harder. I’m up by 6:00 AM most days and often go back to work when the kids are in bed. But I have flexibility around when and how I do my work. And I get to solve interesting problems that leverage my talents and abilities. 

4) Be careful what you wish for—autonomy can be scary 

One of the biggest benefits of starting your own business is you work for yourself. One of the biggest drawbacks of starting your own business is you work for yourself. I remember being a few weeks in and feeling lost. It was mid afternoon on a Friday and I’d just completed everything on my to-do list. I had no idea what to do next. In past jobs, I either had clear assignments or defined objectives to focus on. 

Now, there was none of that. I was the boss, and no one was going to tell me what to do. To be candid, it was scary. I had to create measurements of success then define the daily activities that would lead to the outcomes I was looking for. I was in full control of my calendar. It was a total mindset shift. In some jobs, success requires you to work efficiently. I learned that in my business it was more important to work effectively. 

5) Focus on activity, not reward

In many jobs, there’s a gap between your efforts and the reward of those efforts. This has proven to be especially true in my business. People aren’t buying a physical product, they’re buying me. Occasionally some will want to hire me immediately after we meet, but more often than not it’s going to take time. I can influence people, but ultimately the decision to hire me is theirs. 

Over the last year I’ve learned that all I can control is the inputs. I created an activity scorecard to measure my efforts. This includes daily and weekly activities that put me in a position to be successful. I’ve learned that if I focus on the right inputs, the outputs will come with time. The score will take care of itself. 

6) I waste less time but exert more energy 

In any job, there’s a fair amount of work that has to get done but doesn’t move the needle. You have administrative work. You have to appease your boss. You have to perform tasks that make no sense. You’re expected to be in meetings that are often ineffective. 

Since starting my own business, I spend a lot less time on these things. If I have a bad meeting, it’s on me. If I waste time, it’s on me. But even though I waste less time, I’m often more tired at the end of the day despite working similar hours. Work demands more of my energy. 

7) Working for yourself can be lonely

While I’m more efficient with my time and enjoy my autonomy, I do miss the daily interaction of being on a team and working in an office. I need social outlets and only recently did I learn how much in-person interaction with coworkers filled my social needs. Now that I’m a solopreneur, I have to actively find social activities and build friendships. I’ve joined a community of coaches. I play in two pickleball leagues. To be candid, this adjustment has probably been the hardest thing about starting my own business. 

8) Align with your loved ones

For years I told my wife I wanted to start this business. We debated it. We evaluated what it would take for us to make the leap. We prepared for it. So when I told her the time had come, she was fully onboard. This was essential as there have been difficult moments over the last year and I’ve needed her support and alignment throughout. 

9) Prepare financially

Walking away from a steady salary can be scary. Even if business is good, revenue is going to be lumpy. I knew some months would be better than others. To prepare for this challenge, my wife and I set aside a full year of savings. I was confident I’d be successful and had a spreadsheet with all the financial projections, but ultimately I didn’t know what to expect. 

By building a savings buffer, I made it so year one didn’t need to be a home run. I wanted to build my business the right way and not let short-term financial pressures influence business decisions. I wanted to play the long game. 

My wife and I discussed finances and aligned on a plan. So far, we haven’t had to dip into savings, but knowing that we have a buffer reduces stress and provides peace of mind. 

10) No bad days allowed

I can’t afford to have bad days. My clients need me at my best and expect me to show up to every coaching session energized and focused. To do this, my daily habits are critical. Sleep, exercise, and prayer/meditation are essential. In past jobs, if I showed up to the office at 60-70% capacity I could get through most days. Those days are gone. 

11) Deliver value before asking to be paid

I sell a product that is fairly intangible and it’s unreasonable to think someone is going to hire me because I built a pretty website or explain how coaching can help them. I must deliver real value first. What does this look like? 

I typically have a 30 minute intro call with prospective clients. This is free of charge. I then offer to do a 45-60 minute coaching session that is also free of charge. These meetings require time and preparation, but it’s critical that potential clients see value before they commit. It’s try before you buy. They have to see the value in what I’m offering. 

12) There are no shortcuts, you have to do the work

Two months in, I got introduced to a coaching platform that matches senior leaders with top coaches. There was a robust application process and I put a ton of work into it. I then crossed my fingers and hoped it worked out. I wanted to get picked. 

I thought that if I got accepted, the hard work of finding clients would go away. I could focus most of my energy on coaching instead of business development. After weeks of answering questions and jumping through hoops, I finally got accepted. I was thrilled. But nothing has come of it. It’s been more than 10 months since I got accepted and exactly zero clients have been introduced to me from this platform. 

Thankfully, I didn’t put all my eggs in that basket. Thankfully, it was only a tiny part of my client acquisition strategy. I learned that I had to put in the work to build a business. There are no shortcuts. 

13) Surround yourself with people who will lift you up 

When I started my business, a “friend” of mine kept making jokes about what I was doing. He thought coaching was dumb. He didn’t think it was a viable business. Every interaction we had was negative. I decided I didn’t need him in my life. 

On the other hand, there was an HR exec who was particularly encouraging. I left every interaction with him feeling good about myself and what I was doing. When I shared with him my revenue goal, he said it was a fine target but he was confident I could do better. He encouraged me. He pushed me to aim higher. 

Some people want to see you fail. They’re either not pursuing their goals or not making progress. Your failure makes them feel better about themselves. You don’t need these people in your life. They will drag you down. Find those who will cheer you on and celebrate your successes.

14) Just get started

There are so many decisions I had to make when starting a business. Do I set up the entity as an LLC or S Corp? How much should I charge? How do I find health insurance? What do I name my business? The decisions are endless and they can prevent us from getting started.

When making decisions like this, I’ve learned to determine whether they’re reversible. If they are, just make the decision and get going. You can always change it. Don’t let little things hold you back from making progress. 

Note: I named my business 824 Ventures, a nod to the late Kobe Bryant and the two numbers he wore during his NBA career.

15) Be patient with yourself 

Before launch, I’d gotten to know several amazing coaches and experienced the power of coaching myself. I knew what good coaching looked like and I wanted to be a good coach. But when I started my coaching journey 5+ years ago, I was not good. 

When I was getting certified, I had to record coaching sessions and send them to a senior coach for review. We’d then watch these recordings together and she would tell me where I messed up. It was so painful. One time the feedback was so tough to hear that I almost ended the meeting. 

I’ve made a lot of progress since then, but it’s been slower than expected. Real change and improvement takes time. I still get frustrated sometimes and I have moments where I realize just how far I need to go. I see my clients experience this too. I’ve learned that we all need to be more patient with ourselves. We all need to treat ourselves the way we’d treat a dear friend. 

16) Celebrate your wins 

Too often we hit a milestone and immediately jump to what’s next. I regularly ask my clients to stop and celebrate their wins and successes. When I became a full-time coach, I did the same for myself. For the first few months, every time a new client signed I would celebrate with the kids. Sometimes it was ice cream. Sometimes we’d go out to dinner. Celebrating with them was fun and it motivated me to keep pushing. 

Writing this piece is one way I’m celebrating the success of this first year. I felt called to get into coaching. I felt like it was how I could best use my talents and have an impact on the world. I didn’t launch this business for financial reasons. In fact, I expected to make less than in past roles. I feel very fortunate that my earnings from year one were greater than the highest salary I had. I bet on myself and so far it’s paid off. 

17) Play your own game

When I let people know I was becoming an exec coach, I got a lot of advice. A LOT. Some of the advice came from people I sought out. Much of it was unsolicited. But I’m a collector when it comes to advice. I appreciate different perspectives and opinions. But ultimately, I have to decide what’s best for me. This is my business. 

No one else fully knows what you want to do with your life. No one else has the context you do. Because of this, most advice falls short. Don’t get caught playing someone else’s game. Play your own game. 

If you’ve made it this far, I want to say thank you for reading. This turned out to be a much longer piece than expected but taking time to reflect on year one has been a valuable exercise for me. I wish you the best as you move forward in your career and don’t hesitate to say reach out if I can be helpful.