10 Things You Must Do to Avoid Entrepreneur Burnout

A few years back, I was CTO of a startup that was struggling to grow. We had an established user base, and a decent stream of revenue coming in, but it wasn’t as much as we or our investors wanted. We had plateaued.

We decided to do a hard pivot and create a new product from scratch. Now, not only were we going through the hardcore stress of building a new product, we also had 20 people on payroll who depended on us. Not to mention, we had an existing platform and customers we needed to support.

We made some bad technology choices, some bad hiring choices, and some bad go-to-market choices. Things were coming apart at the seams, and the daily stress was tremendous.

At the same time, my wife gave birth to our second daughter. While this was a bright, shining moment in our lives, it came with the typical sleep deprivation and stress of raising a new infant. I wasn’t able to take any time off, so the stress was just added to the pile.

I wasn’t sleeping, I didn’t have time to exercise or eat well, and I started drinking more to cope. I was fighting with my CEO and my wife on a daily basis. I would wake up at 5am with a rush of panic because I knew I was already behind and there was nothing I could do. I accepted the fact that every single day I was going to fail my family, my company, and myself.

One day, one of my teammates came to me and said I had been wearing the same shirt with baby barf on it for the past three days, I hadn’t shaved in two weeks, I hadn’t cut my hair in months, and I smelled like shit. I took a look at myself in the mirror and didn’t recognize myself. I realized then that I needed to make a change, fast.

I decided to blow it all up. I quit my job, gave up my equity, and took a sabbatical. I spent three months getting healthy. I spent almost every day hiking in the mountains, listening to audiobooks on philosophy and self-help, and clearing my mind. I dissected every aspect of my life, challenged every part of my identity, identified if something was a positive or negative impact on my life, and discarded everything that didn’t bring me joy.

I’ve since adopted a system that has helped me not only cope, but thrive in the high-stress world of building startups. I'm now more healthy, focused, and sharp than I’ve ever been. Now with every coaching and consulting client I have, I get them on the same regimen, and the results are always transformational. My clients always tell me they’re more motivated, happier, able to think more clearly, and make better decisions.

I am happy to share my system with you to help you avoid entrepreneur burnout. These ten things, when done consistently, will keep you on top of your game, and able to sustain the long, rough road that is building a company.

#1. Personal Retrospective

The problem with solving a big problem is that it’s difficult to see and appreciate progress. As a visionary, you may not feel accomplished until the full vision is realized. It’s important that you take time to reflect on and appreciate what you’ve accomplished along the way.

At least once a week, schedule a 15 minute personal retrospective, where you:

• Acknowledge Progress - Look at your completed ToDo list for the week. Give yourself credit for all you got done when you clear your finished items from the list. Celebrate the small wins.
• Appreciate Growth - Think back to a few weeks or months ago, and try to identify areas where you’ve grown. What new skills or tools have you learned?
• Celebrate Customer Successes - When you are focused on the market at large, you lose sight of the individual humans whose lives you’re impacting. Connect with your customers regularly, and try to reflect on one positive impact story per week. Share this story with your team to spread the love.
• Commit to Improve - The core purpose of a retrospective is to continually improve. Set goals for the next week to do things better, even if they’re just baby steps.

#2. Switch It Up

Entrepreneurs thrive on new experiences. When you get stuck in a rut, and keep banging your head against the same problem, it will get you down. Try something different to give yourself some renewed motivation.

• Challenge Assumptions - The first thing to do is zoom out and think about what is and isn’t working for you. What assumptions are you working against that may not be valid?
• Create an Experiment - You probably have a ton of ideas that you haven’t found the time to implement. Create a list of growth hacking or product hacking ideas, and think about the shortest, cheapest way to test each one.
• Try Something Crazy - Sometimes you just have to do something because it’s fun. In your list of ideas, look for things that are “so crazy, they just might work.” Try creating a funny or bizarre piece of content, or add an Easter Egg into your product.

#3. Prioritize Personal Care

This is really the most important thing on this entire list. The Gary V’s of the world will tell you that you need to #HUSTLE 24/7/365 if you want to be successful. The Startup Bro culture makes you believe that you have to be invincible.

We sacrifice our health, relationships, and happiness for our businesses, and it’s counter-productive. You do your best work when you’re rested, healthy, and happy.

In this life, everything screams for your attention, except yourself. You’ve got to take care of yourself if you’re going to make it through the startup journey, which takes 7-10 years on average if you’re successful.

• Sleep, diet, and exercise, in that order - First and foremost, you have to keep your body in top shape to be at the top of your game.
• Meditate - Just take a few minutes a day to find peace and quiet. It’s not only good for your mood, it helps your brain process complex information. There’s a reason it’s become a cliche that Silicon Valley execs all have personal gurus.
• Don’t drink or use drugs in excess - They may relieve stress in the short term, but they actually make things worse over time. Limit intake to 1-2 days a week. If you’re feeling overwhelmed and you want to reach for a drink, go get some fresh air or exercise instead.
• Invest in personal relationships - Your spouse, family, friends, and colleagues are your support group. It’s critical to nurture those relationships and not get stuck in a hole. Not only will they give you perspective and reassurance, they’ll also help you get fresh ideas or connections.
• Spend time in nature - It’s scientifically proven that spending time in nature has a wealth of health benefits. Get out of your office, get some fresh air, and be active outdoors.

#4. The One Thing

There’s a great book by Gary Keller called The One Thing, which provides a framework for accomplishing big goals. In essence:

• Define your big, hairy, audacious goal
• Identify what you can do this year, this month, this week, today, and right now to move you towards that goal
• Break down big milestones into smaller and smaller tasks
• Focus on accomplishing work related to The One Thing over all other work

Create a daily ritual around this. Every day when you’re getting ready for work, think about the single most important thing that will make the biggest impact. Cancel meetings, and defer or delegate tasks that get in your way. Do whatever it takes to accomplish that one thing. Create a special slot in your daily ToDo list. Once it’s done, take a moment to appreciate the accomplishment. Even if everything else falls on the floor, you’ve won the day.

#5. Control Your Calendar

Feeling out of control is incredibly stressful. If you don’t control how you spend your time, you’re like a dog being led on a leash. This causes you to disengage and tune out. If you control your calendar, you control your life.

• Theme days - As I discussed in another article, context switching decreases productivity by almost 50%. Organize your days so that your activities share a common context. Spend one day on product, one day on sales, one day on people, etc.
• Focus blocks - Create recurring 2-hour blocks of time where you will focus on The One Thing. Don’t let any meetings creep into that time. Turn off notifications and find a private place to work. If you aren’t spending at least 2 hours of focused time a day on your one thing, you’re never going to get there.

#6. Set Clear Boundaries

Whatever you’re doing, be fully present and engaged in that activity. If you’re with your family, put your phone away and be fully present. If you’re in a meeting, close your laptop and be engaged in the meeting. Set clear boundaries with your work, family, and personal time.

For me, 5-8:30pm is family time. Everyone in my life knows that they can’t reach me during that time. I plug in my phone in my bedroom so that I don’t check it.

#7. Work in Short, Focused Bursts

Solving complex problems is mentally fatiguing. Just like with physical exercise, you have to take regular breaks. The Pomodoro Technique is a great way to structure your time so that you work in short, focused bursts, followed by a short break to recharge and let your mind process the information.

• Break your daily ToDo list into small tasks that take about a half-hour to complete
• Turn off notifications and put away your phone.
• Set a timer for 30 minutes
• Work until the timer goes off without any distraction
• Take a 5 minute break. Go outside, drink water, have a snack, or just meditate.
• Reset the timer and start again. Repeat this process for two hours, then take a longer break.

#8. Engage With the Community

So many founders I speak with act like they’re solving some incredibly unique problem. The truth is, 95% of what you’re doing has been done already in some form. There are people in your network who are working on the same problems right now and you don’t even know it. Don’t burden yourself with reinventing the wheel.

• Find a support group - Just having people to share your experiences with and help you process your thoughts can be incredibly helpful. Go to networking events, not just because you want to make connections, but because it’s helpful to be in an environment with people like you.
• Join an incubator or accelerator - By joining a cohort of founders at the same place as you, you can share what works and what doesn’t.
• Volunteer and support your scene - Be a leader instead of a follower. Make a name for yourself in your local startup scene, and shape it to be what you need. You’ll create goodwill and a platform to share your experience and ask for help.

#9. Hire Help

As I discussed in this article, successful founders leverage the skills, time, money, and effort of other people to achieve their goals. Every hat your wear as a startup founder is a burden, and the context switching it entails makes you less efficient and effective. You’ve got to find help. All of these services cost money, but when you weigh the cost against the value you can add to your business, it will work out in your favor.

• Outsource menial tasks - There’s nothing more debilitating for entrepreneurs than having to do boring, repetitive tasks. Outsource those tasks as quickly as possible. Use services like Fiverr, Upwork, and MTurk to outsource low-level work.
• Outsource tasks that you’re not good at - Know your strengths and weaknesses, and hire people to do things that you’re not good at, and will take you a long time to get done.
• Automate personal life - Just maintaining your body and your household takes up a major portion of your time and energy. Try to automate your personal life so that you have more time to invest in your work and things that bring you joy and energy. Use services like Instacart and TaskRabbit to outsource your shopping and errands. Hire handymen, gardeners, and cleaning services to maintain your household.

#10. Find a Mentor

Finding a good mentor will help you avoid mistakes, gain perspective, make connections, and find new ideas to try.

Don’t be afraid to reach out to more experienced or successful people in your network. Most people want to help, and especially people later on in their career want to give back to the next generation of founders. In this article, I provided a template you can use to approach potential mentors.

You can also benefit from hiring an executive coach. I’ve been coaching technical executives for over a decade and can provide you with a structured framework for achieving your goals. My coaching clients have added millions to their bottom line, while living a more fulfilling, stress-free life. I am happy to provide you with a free one-hour intro call, so please reach out!

Conclusion

I want to challenge you to reflect on these ten things and assess whether or not you’re setting yourself up for success or failure.

It’s my mission in life to help founders succeed, and keeping their heads above water is job #1. I would love to hear about your struggle with entrepreneur burnout, so please leave a comment or DM me!