On Taking Breaks
I’ll be honest, I’ve never experienced burnout.
I’ve always enjoyed my work, especially since I went full-time self-employed a couple of years ago. I have always been pretty good about balancing my personal, fitness, and professional efforts, so I’ve never reached the breaking point that results in real physical burnout symptoms.
That said, I still think taking long breaks from workis important.
Ever since I started Draft.dev, one of my key leadership metrics has been measuring my ability to take time off.
Let me also point out that by “take time off,” I mean really taking time off. When I take a break, I don’t check email, answer work questions, or schedule meetings with anybody. I turn on my auto-responder and check the f*** out.
Last year, my goal was to take a 2-week break from the business and this year, when my wife and I found out she was pregnant with our second, I made it my goal to take 4 consecutive weeks off from the business.
I’m currently entering week 3 of that 4-week break, so I thought I’d reflect on some of my observations. I’ll also share some of the leadership and delegation strategies that have enabled me (and everyone in the company) to take extended leave, despite having only around 16 full-time employees.
1. I’m Reinforcing Healthy Detachment
Like most entrepreneurs, I am pretty attached to my business. It hurts when customers cancel, and the fear of failure often keeps me up at night. After about a week of disconnecting from work though, I realized that a lot of that anxiety was gone.
By taking time away from my business, I’m able to prioritize it more appropriately as just something I do, not my entire life. I feel less worried about failure because I see the other things I have in my life (family, health, and friends) more clearly.
I’m also seeing some issues we’ve been facing much more rationally. For example, I have been worried about some short-term challenges that the team is facing and putting off dealing with them in the way I know we need to. Stepping back has helped me realize that I know what I need to do; it’s time to just take action.
2. I’m Living More in the Moment
I have been in a bad habit of diving into emails while my son eats breakfast and gets ready each morning. This puts me behind an LED wall that has been preventing me from enjoying our time together.
I’ve found that disconnecting from work has allowed me to be more present with my family and more conscious of the moment at hand.
I’m not thinking about my day’s meetings because I don’t have any meetings to think about. I’m not living in the “what’s next” because there’s really not much happening today or tomorrow besides the moments at hand.
This has been really rewarding, and while it’ll be harder when I’m back at work, I’d like to continue practicing living in the moment more.
3. I’m More Disciplined About Working Out, Eating Right
A big part of maximizing my energy is tied to how well I’m eating and getting activity. Even though I’m currently sleeping pretty poorly because of a cold and a restless infant, I have been able to plan my meals and move my body more throughout the day.
Physical fitness is a long-term investment in your success, so while there are short-term benefits (focus, energy, positivity), the real benefits won’t be felt for years. Taking a month off work to focus solely on family, fitness, and personal introspection has helped me remember how important this is.
Setting Yourself Up for Breaks
When I tell other people that I’m able to take an entire month off, they typically look shocked. Since so many people ask me how I can do it, here are a few of the specific strategies I have used:
1. Don’t Offer Services You Can’t Replicate
The most fundamental problem most small business owners have when trying to take a break is that they offer services only they can provide.
If you bill clients for access to your brain as a consultant, if every project requires you to estimate and invoice the client, or if your sales call is so complex that only you can do it, you’re not going to be able to take time off without sacrificing revenue.
2. Document and Delegate
Most small businesses are brittle because they rely on the founder to make sales, handle customer issues, or hire other employees. As the founder, I have had to do all these tasks (and hundreds more), but I have a habit of making them into processes.
The first time I have to do something, I’ll figure it out. The next time I do it, I’ll write down the steps or record a Loom video. Then, the next time I need to do that task, I’ll try delegating it to someone else. In the past year, I’ve delegated sales, marketing, payroll, contract review, and monthly financial reconciliation to others on the team.
3. Let Fires Burn
Finally, there will undoubtedly be issues that arise while you’re gone. If your team is so used to coming to you to solve every problem and answer every question, they will really struggle when you’re taking a break.
So, you have to practice letting other people solve problems by not solving them all yourself. You have to let little fires burn; let people f*** up; then instead of blaming them, help them learn from that mistake. By making mistakes, your team will learn more, and by treating mistakes with grace, you’ll help them see that they are allowed to make their own decisions, even if they’re wrong.
Ultimately, you have to think long-term instead of short-term.
In the short-term, it’s better for you to swoop in and solve every customer issue as quickly and perfectly as possible.
In the long-term, it’s better to let your team make mistakes and learn from them so you aren’t required to do so.
Conclusion
I plan to continue taking 3-4 weeks off every year.
The clarity I have gotten from this break has been well worth it, and while I’m sure I’ll come back to some issues at work, I’m mentally more equipped to handle them objectively now.