Working Hard, Sustainably (Sort of)

When I was running my company, I heard the same thing over and over again from more seasoned CEOs: “if I could go back and do it again, I would have taken better care of myself. I would have worked less, taken more time for other things, taken more time off.” Their advice is to do what they should have done and have a more balanced life.

I always kind of tilt my head sideways when I hear comments like that one. Yes, you would have worked less if you could do it over again, but whatever you did worked, didn’t it? What you did, not what you wish you did, got you to a position where you’re talking to me now. Shouldn’t I learn more from what you did than what you wish you had done? I want us all to recognize something: the job you’re doing is hard. Challenging, exhilarating, fulfilling… but hard. Mine is certainly all of those things, and I know that being successful probably means working way more than 40 hours a week.

Therefore, I’m not going to give you some empty advice about working less on the thing you’re most passionate about. You’re going to be thinking about your company pretty much 24/7, even when desperately trying to focus on something else. You’re going to feel guilty for not working whenever you’re not, and you’re going to feel like the pile of work never seems to get smaller when you are. But somehow, you love every moment.
But while you’re delightfully working your ass off, there are some things that might make that level of work just slightly more sustainable. You may love it, but you’re probably not immune to stress (if you are, please run for President). Here are some things I did:

• Have go-to retreats. You’re going to have moments where you know you need to escape. That’s inevitable, but the problem for me was that I didn’t know how. I didn’t know what to do with myself, and I certainly didn’t want to take the time to plan a retreat. So I established my go-to things that rejuvenated me, so I could fall back on them whenever I needed it. They can take different forms, but think about personal retreats that take 30 minutes, 3 hours, and 3 days. For me, I would go to the gym for 30 minutes, play computer games for 3 hours, or head to a bed and breakfast I knew of about an hour outside of town for 3 days. If you’re like me, you’ll find that you use your 30 minute option once every couple of days, your 3 hour option once every couple of weeks, and your 3 day option once every couple of months. Give yourself the space to retreat, you’ll be better at your job if you do.
• Don’t sacrifice your health or your family. It’ll often seem like the precious hours spent with your kids or significant other or the time spent running, biking or in the gym can be better spent getting things done (or at least multitasking). Guard your time spent on your health and on your family extremely jealously. There are lots of habits you’re going to build that are unsustainable: you’re not going to get enough sleep, you’ll have a lackluster social life, and you’re not going to do much in the way of vacations. But protect those two things. Anything else is doing a huge disservice to all involved, including your company.
• Get a coach (or three). No matter where you are on your journey, there is someone who has been there before that can help. With the right relationship, that person can not only listen and empathize (then again, your friends or significant other can do that), but provide actionable advice and an outside perspective for those times you’re too in your own head. Some of the most successful CEOs I know have hired coaches after their companies have gotten to the Series A or B level. But the coaching doesn’t have to be formal: the idea is to find people that have walked your path before and bring them into your circle. When I was running my company, I had 2 or 3 other CEOs (all a little further along than I was) on speed dial, and I wasn’t afraid to spill my guts. Whoever it is, ask to meet with them regularly; I’ve found even the busiest people will make time to listen to a promising entrepreneur.

Remember: you got into this business because you have an irrational belief in yourself, that you can do bring an awesome product to life and have a positive impact on people’s lives. Don’t let go of that. It also takes a ton of elbow grease in order to get it done. Especially early on in a company, you’re going to push yourself harder than you ever have before. That means doing things that aren’t sustainable, and that’s ok. But be thoughtful about the tradeoffs you’re making, and protect the things that really matter.

Here’s to the journey!