Founder mental health and wellbeing hacks

This week is mental health awareness week.

It’s hard to be a founder

Starting a new business is hard. Really hard. You quickly find that your entire life can be consumed by it. Notions of work-life balance can go out the window. Stress levels rise. After doing this for a week, a month, a year, several years – and it almost inevitably takes a lot longer to achieve success than anyone wants to believe or admit – you may find that your ability to be superhuman 24/7 starts to crack a bit.

The weight of expectations

There are so many expectations. You want to be primed to recognise opportunity when it knocks, and answer the call swiftly and brilliantly – this is the very essence of being an entrepreneur. You want to be successful, and appear to be successful, as success breeds success. You want to constantly innovate, do novel things that break the status quo. You want to be ever inspirational, motivating everyone around you to get in behind your idea and business. You need to read heaps to stay up with industry trends, the future, the competition, and your customers. You’re always selling. You need to be super strong, getting up again and again after each knock, brushing yourself off, putting your best smile back on, and going into the fray again. You’re likely working across multiple time zones, as Aotearoa New Zealand is so far away from our key markets. You’re probably functioning on a lot less sleep than would be ideal. Your family often wonder if you’re even speaking the same language. Who knew you’d need to learn how to be a lawyer, an accountant, a salesperson, an HR specialist, a politician and a software guru? And money. Juggling debtors, creditors, payroll and taxes. The end of the runway is always there, staring at you, maybe from a distance, but more likely from an ever decreasing range. If you’ve taken investor money – how can you tell them that things aren’t going quite as planned but you now have an even better way forward but it may require a bit more cash? How will you ever face the world again if your company craters?

It makes leaping tall buildings in a single bound look easy.

But it isn’t easy, it’s hard. Really hard. 24/7. For the foreseeable future. And maybe beyond. It’s a pan-galactic ultra marathon.

I’ve been to these places myself, and I’ve been shoulder-to-shoulder with many founders who were in these places. Here are a few techniques I’ve found to be helpful when things started looking a bit dark or careering out of control.

Your overall attitude

Be kind. This is the main thing. It shouldn’t be the main purpose of being kind, but if you are kind on a consistent basis, other people will be kind to you. You’ll really appreciate this when things aren’t going well.

Be especially kind to yourself. Be as kind to yourself as you would be to a good friend. Why wouldn’t you? If your inner voice is berating you, stop and think: would you treat a good friend this way? Things are going to be a lot tougher if you’re not a friend to yourself.


Know your purpose, and stay true to your mission. Do you remember why you became a founder? What was the higher-order purpose you wanted to achieve? Hint: if it’s “make shiploads of money” that might not sustain you through troubled times. But something which benefits the world or your community will. Convince yourself that what you’re doing and going through is worth it to attain the purpose. If it isn’t, it might be time to pivot.

Focus on goals. It’s easy to be distracted by the million things you need to do. What’s the most important (even though it may not be the most urgent)? How can you ensure that you have the time, attention, and resources to achieve the critical goals? It’s tempting to work on things we like doing, or things that are easy to do, but ultimately those things probably won’t get us to the place we need to be.

Manage your time. I’m a slave to Trello. I have my big goals laid out in their own column, along with columns for backlog, things I want to accomplish this month, this week, today, critical items, next up, things that are blocked, things that have been completed this week, and a monthly scrap heap for things that are no longer worth doing. Shuffling those Trello cards from left to right gives me a sense of accomplishment, especially when I feel I haven’t done much. At the end of the day I can look at the done column and see evidence that I have done quite a bit. If a new email comes in that I have to deal with in more than a cursory way, it gets a Trello card. Any new actions go into the today column, and get shuffled back to the appropriate column at the start of each day. Trello isn’t the only tool for this, some people prefer to-do lists. The important thing is to organise your tasks and not let them build up as a frighteningly unassailable amorphous knot. You can and will conquer them piecemeal.

Delegate. OK we get it, you’re a perfectionist and an overachiever and you like things done just so. The problem is, that’s not scalable, and as your list of things that need to get done grows with your business, you need to gather others around you to help you out. If you’re out of time, and there’s a possibility of getting someone else to do a task on your list, do it. And think, what would it take to get someone to help lighten your load?

Eliminate your lowest priority of stuff to do. If you’re super busy, and you can’t delegate, you probably need to get comfortable with the fact that some things just aren’t going to get done. Shuffle them into the scrap heap, and then you can focus on the stuff that matters with less clutter.

Schedule times without meetings or interruptions. Some of us could spend our lives in meetings. Sometimes, we just get started on an important task that requires solid thinking or creative time, only to be interrupted by a call or DM. My diary has Mondays as “sacrosanct desk time” – this is the day of the week that I strive to get as much stuff done at my desk as possible. I try not to look at email or other message clients except immediately after lunch. Thursdays I have a “meeting free zone” when I’ll take calls, but again try to just plow through work that requires full attention. In reality, I end up taking calls and meetings at these times but the key thing is that they’re on my terms. That helps my sanity a lot.

Turn one hour physical meetings into half-hour Zoom calls. If someone I don’t know well wants to meet with me for a coffee, I ask them instead to do a half-hour Zoom call. In general this is a much more efficient use of time – it’s limited to a half hour, and there’s no travel to get there and back. If it’s a meeting where I think there will be real value in talking for 50 minutes face-to-face, we can schedule that but generally not on the first date. Setting expectations for a short meeting means you can generally cover almost as much ground in that half-hour as you might have covered in an hour.

Anything worth doing is worth doing badly. This is one of my partner Kate Frykberg‘s favourite quotes, which originally came from Christian philosopher GK Chesterton in 1910, and is a restatement of Voltaire’s “perfect is the enemy of good”. Sometimes it’s important to just get something done, and you’re not going to have time to polish it, until having that thing polished is important.

Make space for regeneration and recovery

When you’re feeling down, schedule a small amount of time to do stuff that you enjoy and are good at. Sometimes, in the morass of working on something where you’re making no headway for a long period of time, it pays to take a very limited time out (say an hour) to do something you enjoy and you’re good at, just to remind yourself that you’re effective and can produce results, and remember what it feels like to win. For me this is programming. I’ll clean up a configuration file or write a short shell script to automate something that’s been annoying me. At the end of an hour, I will be able to say that I’d done something useful that day, and remind myself that I’m not half-bad as a software developer. Baking works well too. You’ll have your own ways of achieving small wins.

Schedule downtime. No one can work 24/7. Many founders try to work crazy hours for extended periods of time. That’s great if you can do it, but chances are you’ll be more effective if you schedule some time to yourself or with people you like or love in a non-work environment. You’ll come back refreshed and much more effective than if you keep trying to push your depleted self at the front line. At a minimum, I try to take Saturdays off and not touch a computer, or look at my email app on my phone.

Pause to reflect regularly. Being an entrepreneur is all about constant learning. You’re at it nearly 24/7, and it’s easy to get so caught up in the minutiae that you can’t see the forest for the trees. I encourage people to keep a diary, or even better a lab notebook, so they can go back weeks, months, or years later and reflect on what they learned. I try to integrate reflection into my weekly planning. It can be as simple as, “What mas the most important thing that happened last week?” “What can I learn from that experience?” “How will I integrate that into my future practice?”

Yoga and meditation. Yoga calms the body, and prepares the way for meditation which calms the mind. With so much overstimulation from the million things you’re busy doing, you need some space to regenerate and foster creativity. It takes practice, but yoga and meditation can greatly increase your resilience and unflappability. The inner calm that regular yoga and meditation practice provides increases your ability to find the right perspective to integrate, react to, ignore, or deflect difficult challenges. Yoga and meditation have saved my life.

Look after your body

Eat and sleep well. It stands to reason that if you’re not giving your body the basic things it needs, it’s going to affect your stamina and mental health. Eating well isn’t that hard, it just means taking some time to get good ingredients and make them into a balanced meal. It’s a good break from work, and doesn’t need to take a long time or be fancy. Sleeping well can be trickier. Shutting down my computer and phone an hour before bedtime, and winding down properly by reading a book, playing a game, or listening to soothing music helps clear my mind of what I call the tumble dryer of ideas which could keep me awake indefinitely if left unchecked. Alcohol and drugs are generally unhelpful in the longer term. While they may seem like a good shortcut to stamina, relaxation, or just taking a break, they can overtake your ability to resist becoming dependent. I’ve seen at close range alcohol kill a good friend, and meth and coke severely disable great entrepreneurs. Obviously, they hadn’t planned on that. You can plan to avoid that fate.

Get outside, exercise, and stay fit. Doing these things help keep you grounded, and keep your mind clear. Getting outside is also a great chance to be grateful for nature and the world around us. You don’t need to do this often or in a sustained way either. If 5 minutes is all you can afford, just do it, and start the virtuous cycle of looking after yourself properly.

Dealing with uncertainty and learning from it

Trust your gut. It’s easy to experience input information overload as a founder. There comes a point where each incoming datum actually subtracts value from your ability to make a decision. And yet, you can’t afford to dither, like a possum in the headlights. This is the time to trust your gut. As an entrepreneur, you’ve developed a sixth sense through observing patterns, and in a world full of imperfect and incomplete information, sometimes that sixth sense is your best bet. Make a decision, and move on.

Failure is just information. If you try something and it doesn’t work, don’t mourn, even if the failure was painful. They say failure is a much better teacher than success, so learn what you can – what exactly went wrong? what should you have learned about the situation before going into it? what could you have done differently? – make a mental note, draw a line under it, and move on. Congratulations, you are now smarter than you were before the failure. One entrepreneur I worked closely with rated each of his experiences as “three out of five”. He sought to treat all inputs equally no matter how good or bad they might have seemed to others. I was worried that he was depriving himself of exhilarating emotional experiences. But when he sold his startup in a strategic trade sale, I asked him, how did you rate that experience? He broke character and said “that was definitely a five out of five!”

Celebrate your achievements, especially with your team. Again, there are so many urgent things to do as a founder, that you might achieve something great, but you can’t pause to celebrate because the next urgent task is beckoning. Revelling in success, even if briefly, helps set up a virtuous feedback cycle, especially if you’re celebrating as a team. It’s an opportunity to appreciate each other, enjoy the fruits of your labour, and remember what it likes to feel great rather than there’s another task pressing to be completed.

You are not alone

Don’t let your important relationships slide. Yes, your business is all consuming, but don’t let it consume your most important relationships, like your partner, family, or close friends. Your relationships with other people outside of work help balance your relationship with your business. It can be very lonely being a founder – no one who hasn’t done this really understands what you’re going through, the demands are huge, immediate, and unavoidable. Maintaining close relationships with at least one other person might be what saves you if things get really difficult.

Get a mentor or confidant. This could be someone who isn’t part of your business, but someone who understands what you’re going through. Someone you can just dump on. It’s really hard being a founder or CEO, because you often feel you have to act superhuman. You can’t really dump on your colleagues because it might sour the relationship. You can’t dump on your investors or board members because they might lose faith in you. Having someone you can just talk to or complain to can be a life safer, especially if they can deeply empathise with your diverse emotional states.

Know when to yelp for help. If you’re suffering, you don’t need to do it alone. If you stop to think about it, there are a surprising number of people who care about you, even if they haven’t said so. If your close personal relationships aren’t working well enough, reaching out to other founders or people in the ecosystem can be helpful. We don’t often talk about it, but many of have been in similar circumstances. And there’s always your doctor who can refer you to a therapist if need be. There is no shame in this – you would get help if you were having physical health issues, why wouldn’t you seek help for mental health issues?

Be grateful. As founders, we all have so much to be grateful for. What a privilege to be able to run your own business and execute your own ideas! We have our teams, our communities, our families, the coolest tools and tech that have ever existed. It’s especially important to practice gratitude when you’re feeling down. Thanking people for small things builds social fabric, and feeds a virtuous cycle helping those around us to feel good about themselves and their relationship with you and others. A number of studies have shown that gratitude can be cultivated and lead to lower levels of stress and depression. Even if the world is crashing down around you, you can find things to be grateful for. You’re alive. You’re not starving. You have a roof over your head. You live in a beautiful country. You have friends and colleagues who care about you. You have achieved an amazing amount despite all the odds. Daily practice makes gratitude become a habit, and much easier to do in hard times. I begin each day by literally thanking God that I’m alive. The rest follows naturally.

When things get really tough

Avoid catastrophising. No matter how dire your circumstances are, there is almost always a way out. Finding the way out depends on taking a cold hard look at what the real issues are, and outlining a set of steps to overcome those issues. The outcome might ultimately be painful, but it’s rarely as bad as what we imagine as we lay awake in bed panicking at 4am. Think: what is the absolute worst case scenario? What is the likelihood that it will actually happen – usually it’s really low. How would you recover from that scenario – usually there is a clear path, which might involve significant loss, but you’ll walk away in a state from which you will be able to eventually rebuild. Now that you’ve outlined the worst case scenario, and admitted that the probability of it happening is low and that you’ll survive, you can move on to the likely case scenario, and start working on practical steps to work with it outside of the shadow of an unlikely catastrophe. But don’t forget about the best case scenario! What does that look like, and how can you bring that about?

In my experience, things generally work out one way or another. And much of the time failure isn’t as bad as it might initially seem. My biggest failures have been the wellspring of my most remarkable successes. The failures felt crap at the time, but looking back at them from the perspective of years or decades, they were a critical part of my personal development and my later success would not have been possible without the earlier failures.

The retrospective prime directive. And even if you do fail, hopefully no-one will be able to accuse you of slacking off or approaching what you were doing with bad intentions. As a founder, you’re out there every day working hard, hoping to achieve great things for yourself and those around you, against seemingly impossible odds. When people look back at what you’ve done, hopefully they’ll begin with the Retrospective Prime Directive:

Regardless of what we discover, we understand and truly believe that everyone did the best job they could, given what they knew at the time, their skills and abilities, the resources available, and the situation at hand.

In conclusion

I feel bad about the clickbaity title of this post, so if you made it this far, please accept my apologies. I don’t think it’s really possible to ‘hack’ your way to good mental health or wellness – attaining and maintaining wellness requires a pattern of behaviour, practicing a number of things on a regular basis. And many people don’t realise they’re lacking this practice until it’s too late. I’ve been told that it’s much better to avoid burnout than to try to recover from it, as the avoidance requires a lot less effort and pain than recovery.

Go well and be well.

Have I missed anything? If you have any additional mental health and wellbeing tips, please share them in the comments.

Disclaimer: I’m not a therapist, and I’m not a mental health expert. I don’t pretend to know everyone’s circumstances. I hope at least some of these techniques will be useful to you, and bring you peace of mind, success, or release. Your mileage may vary.