My Peers Confronted Me About Being a Workaholic. These 5 Changes Helped Me Build and Sell Companies With Less Stress.
Seven hard-earned lessons can help entrepreneurs manage burnout, protect their identity and finances, build stronger support systems and create a successful life beyond the business.
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Key Takeaways
- Delegate real responsibility, not just tasks, and create a daily routine that helps you leave work mode behind when you get home.
- Separate your identity from your company, lean on people who will tell you the truth and use clear milestones to turn big risks into manageable decisions.
Back in 2017, I was confronted by a group of fellow business owners. We belonged to a peer group that met every month to help each other work through the challenges of running companies.
But this meeting was different. It was an intervention of sorts. They confronted me about being a workaholic, and they were right. My entire identity was wrapped up in being a successful businessperson. But my personal life was far from successful. I had let my health deteriorate. I had missed too many family moments. I was burned out from constant travel. And I had convinced myself that this was simply the price of being an entrepreneur. It wasn’t.
After that intervention, I began taking a more balanced approach to life. I started CrossFit, which I still do today. I took more vacation time with my family. I began delegating responsibilities instead of just tasks. I stepped out of the limelight and let others run the company. Eventually, I resigned as president of my company and appointed an all-star leader in my place.
My life has been much better since then. And ironically, I’ve become even more successful at starting, scaling and exiting companies. The difference is that I now operate more like a coach to leaders than the person managing every detail of every company. Here are five ways I learned to survive the toll of entrepreneurial life.
1. Delegate responsibilities, not just tasks
Entrepreneurs don’t have 9-to-5 jobs. Too many times, I’ve been awake at 3 a.m., worrying about problems inside the company. But I eventually learned that delegating tasks isn’t enough. If you delegate only tasks, you’re still carrying the mental weight. You’re still the person responsible for every outcome.
The real shift happens when you delegate responsibilities. When you put the right leaders in place and give them true ownership, you stop being the bottleneck and stop carrying every problem in your head. Today, I don’t worry about certain areas of the company because I know strong leaders own them.
And yes, I sleep through the night.
2. Create a daily routine to shift from work mode to home mode
My wife used to tell me, “Stop barking orders at me when you come home.” She was right.
I have a very clipped, direct communication style. In business, that can be useful. I move fast, make decisions quickly and give direct feedback. But when I brought that same style home, it didn’t work. My family didn’t need a CEO walking through the door. They needed a husband and a father.
So I created a routine to help me transition from work mode to home mode. Mine starts with a session in the hot tub, followed by changing into comfortable clothes. A friend of mine changes into a different pair of shoes when he gets home. It doesn’t have to be a big thing. It just needs to signal to your brain and body that the workday is over. Trust me, it’s better than relying on alcohol or other unhealthy habits to wind down.
3. Remember that your identity isn’t your position in the company
I once watched a friend’s business collapse after a spike in interest rates. For years, his company had been very successful. Then, almost overnight, everything changed, and he had to lay off his entire workforce and shut the company down. Watching him go through that was a painful reminder that founders need to separate business failure from personal worth.
Too often, our identity is tied to what we do. But every entrepreneur knows business is a roller coaster. There are wins and losses, internal failures and external shocks, and moments when things happen completely outside your control. Your company is something you’re building. It isn’t who you are.
When I fail at something, I remind myself that although I failed at this one thing, I’ve succeeded more than I’ve failed. That perspective matters. Failure is part of the entrepreneurial journey, but it should never become your identity.
4. Make time to connect with others
I don’t think I would have recognized how out of balance my life had become if my peer group hadn’t pointed it out. It takes a village to run a startup, and it also takes a village to survive being an entrepreneur.
Connecting with others can make a major difference, and I don’t just mean joining a networking group. I mean finding people who can really help you: people who know you, people who can challenge you and people who can tell you the truth when you’re too close to a situation to see it clearly. I’ve also seen a psychologist to help me deal with the emotional toll of the entrepreneurial roller coaster. That helped me reframe some of my thinking and better manage the stress that comes with building companies. Reaching out for help isn’t a sign of weakness. It’s a sign of confidence and strength.
5. Set SMART stage gates
When I launch a startup, I set very specific stage gates. The idea comes from product development: You break a project into stages, and at the end of each one, you hit a checkpoint where you decide whether to keep going, change direction or stop. I make sure each gate is tied to a goal that’s specific, measurable, attainable, relevant and time-bound. For example, a gate might be landing a certain number of paying customers within six months.
This matters because entrepreneurs are surrounded by naysayers. When you launch a new venture, people will tell you why it won’t work. They’ll point out the risks, tell you who has already tried it and give you every reason to be afraid. The fear of loss and embarrassment kicks in, and that noise creates stress. Stage gates give you room to breathe. Instead of worrying about whether the entire company will succeed, you focus on the next clear milestone. If you hit it, you keep going. If you miss it, you either pivot or kill the idea.
Stage gates don’t remove the risk, but they help you manage it. They turn the chaos of entrepreneurship into a series of clear decisions.
Success doesn’t have to cost you everything
For years, I believed burnout was simply the price of building companies. It took a room full of honest friends to show me I was wrong. Delegating real ownership, leaving work at the door, separating my identity from my business, leaning on others and breaking big risks into manageable steps didn’t slow me down. They made me a better leader and a more successful entrepreneur.
You don’t have to choose between building a great company and having a life worth coming home to.
Key Takeaways
- Delegate real responsibility, not just tasks, and create a daily routine that helps you leave work mode behind when you get home.
- Separate your identity from your company, lean on people who will tell you the truth and use clear milestones to turn big risks into manageable decisions.
Back in 2017, I was confronted by a group of fellow business owners. We belonged to a peer group that met every month to help each other work through the challenges of running companies.
But this meeting was different. It was an intervention of sorts. They confronted me about being a workaholic, and they were right. My entire identity was wrapped up in being a successful businessperson. But my personal life was far from successful. I had let my health deteriorate. I had missed too many family moments. I was burned out from constant travel. And I had convinced myself that this was simply the price of being an entrepreneur. It wasn’t.
After that intervention, I began taking a more balanced approach to life. I started CrossFit, which I still do today. I took more vacation time with my family. I began delegating responsibilities instead of just tasks. I stepped out of the limelight and let others run the company. Eventually, I resigned as president of my company and appointed an all-star leader in my place.