Why Founders Need to Be Their Own Good Boss

Written by Dave Bailey

Filed under founders leadership psychology

Founder working poorly over night

Startup founders often neglect their wellbeing, but the truth is your health affects your ability to build a business. Here are key tips on how you can look after yourself without neglecting the business.

Do you ever feel guilty when you’re not working on your startup? You’re not alone . . . and if guilt is stopping you from looking after yourself, it might be worth revising your assumptions.

One afternoon, I had a session with one of my Series B CEOs. After saying hello, he said, ‘I feel so guilty, Dave — I just spent the morning working from home. I got so much done though. It was awesome.’

Sometimes it’s my job to ask dumb questions. ‘If it was so productive,’ I said, ‘why do you feel guilty?’

‘If I’m not in the office, I feel guilty,’ he said sheepishly. ‘I feel guilty on weekends too. And it’s probably why I haven’t taken a vacation in the last two years. Do you know what I mean?’

Of course, I did.

Every founder knows the feeling all too well. 

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Where does ‘Founder Guilt’ come from?

No-one gets to become the CEO of a company without taking on obligations. There are staff who depend on the business for their salary, investors that expect some sort of return, and, hopefully, customers who want a good experience.

For founders, this obligation is particularly personal because without them, no one would be there. A growing number of people put their faith in the founders’ dream and while it’s exciting, it’s scary too.

All of the problems that no-one else in the company can solve end up with the founders. And when you’re constantly bombarded with problems, it’s easy to feel as if you’re doing something wrong.

If a team member is struggling, am I not doing a good job of managing? If the product isn’t growing fast enough, am I giving poor direction? If I receive a negative comment from an investor, am I killing our chances for follow-on investment?

Guilt can be a strong motivator to work harder. Many founders work themselves unhealthily to the bone, but work isn’t enough. With limited time in the day, saying ‘yes’ to one thing often means saying ‘no’ to something else.

Sometimes it feels like you’re constantly letting someone down.

It’s time to be your own good boss

Looking after yourself isn’t optional. If you stop the fundamental activities that keep you operating at top performance, it will eventually catch up with you (and faster than you think). The question is:

What are your obligations to yourself?

When I first heard this question, I was at a loss. I’d been so focused on my obligations to others that I’d never even considered that I had obligations to myself.

So I flipped it on its head, and asked myself a different question:

How do I expect my colleagues to look after themselves?

Have you ever noticed that it’s easier to give advice than to take it? As I listed the ways I expected my colleagues to look after themselves, a sudden and unexpected realisation dawned on me: I needed to hold myself to the same standards.

Here are some of the self-obligations that I identified which I believe are essential to perform at our best.

1) Getting enough exercise.

Have you ever noticed that it’s easier to resist junk food and alcohol after going to the gym? Physical exercise focuses your mind and increases your willpower. I’ve noticed that this doesn’t just apply to decisions about food and drink; exercise makes it easier to say ‘no’ to other non-essential things that you might otherwise say ‘yes’ to out of guilt.

Rule of thumb: Exercise 3–5 exercise sessions per week — you’ll be in great company.

2) Spending quality time with friends and family.

‘I need to stay late to finish this board presentation — can we postpone?’

But after postponing three times, you aren’t invited again. And similarly, when a venture isn’t going to plan, you start avoiding people. Even the question, ‘How are you?’ becomes scary. What if you accidentally tell the truth and say, ‘Things are pretty awful. We’re constantly on the verge of bankruptcy and I feel like I’m in way over my head — but enough about me, how are you?’ (If you’re nodding along to this, then you really need to organise a dinner, pronto!)

Rule of thumb: Two meetups with friends per week — it’s proven to improve your health.

3) Eating well.

A year into my last funded startup, I was overweight and my energy levels took a nosedive. I’ll never forget taking a vacation in Brazil where my old friends said, ‘Dude, what happened to you?’

My answer was something like, ‘My startup happened to me,’ but it would have been more accurate to say, ‘I regularly miss lunch only to gorge on sugary foods in the afternoon and eat a late dinner from the restaurants nearest my office, since there is no food in my fridge.’

Like the man said, ‘You are what you eat.’

Rule of thumb: No more than three unhealthy meals per week — aka the ‘Three-meal rule’. 

4) Prioritising sleep.

Sleep — what a luxury, right? Olympic athletes don’t stay up until 3 a.m. the night before a big race since it would obviously impact their performance, but it’s harder to measure our performance at work on a daily basis. It’s difficult for us to connect the dots, yet sleep is essential, not just for high performance, but for civil interactions with other humans — it’s all too obvious in a meeting who didn’t get enough sleep the night before . . .

Rule of thumb: No more than one late night per week.

5) Solitude.

Growing startups create a never-ending torrent of distractions and problems and your desk isn’t always the ideal environment for deep thought. While it is your job to deal with issues appropriately, it’s also your job to reserve time to be alone. In Lead Yourself First: Inspiring Leadership Through Solitude by Michael S. Irwin and Raymond Kethledge define solitude as ‘freedom from inputs from other minds.’ It’s ok to work outside the office to get the calm you need.

Rule of thumb: Two phone-free walks per week — and that means no podcasts, sorry!

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6) Training/coaching.

Great companies know that they need to train their staff to be the best. As a CEO, investing in yourself has a massive payoff — you are one of your company’s most important assets. Training and coaching aren’t the same as ordering an extra bottle of Bollinger at your launch party, so don’t treat them as such.

Rule of thumb: Invest in training/coaching course every three months.

7) The right to say ‘no’ to nonessential meetings.

Each of the activities listed above takes time — and saying ‘yes’ to them means saying ‘no’ to something else. Take a good look at your calendar from last week. How many of those meetings were essential? Heck, how many of them were even useful? Just because you’re invited doesn’t mean you need to go. It’s time to check your priorities.

Rule of thumb: Keep 25–50% of your calendar unscheduled — for your own agenda.

8) Taking a vacation

Yes, even startup founders are allowed a trip from time to time. One of the hardest things to find in a startup is perspective — and one of the easiest ways to get it is to put some distance between you and the company. Trust me, you’ll be amazed at how well your team gets on without you.

Rule of thumb: Take a two-week vacation every six months (Europeans have this right!)

Are you keeping score?

Try this little exercise. List out these self-obligations, or come up with your own, rate yourself from 0 to 10 on how well you’re meeting them.

How well are you eating? How much exercise are you getting? What is the quality of your sleep? How healthy is your social life? If you’re getting a poor score, it might be time to set aside more time to look after yourself. In the words of Top Gun’s Captain Jordan, ‘Your ego is writing checks your body can’t cash.’

Continue reading about startup wellbeing: 

Originally published Jun 4, 2019, last updated Apr 9, 2024

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