How to survive the stress of leading a startup

Let me ask you a question, and think about it for a second before you answer: Have you ever been totally bored and completely stressed out at the same time? Right? Me too. It’s actually pretty common in startup leadership circles, but no one ever realizes it until someone asks them the direct question. I recognize that kind of stress all too well, but it took me most of my 20 years working with startups to recognize why it was happening.

Good stress comes from loads of work aimed toward a desired and achievable goal. This bad stress isn’t the same. Bad stress happens when you’re doing a hundred things at once, but none of them feels like parts of a greater sum. Bad stress makes you do stupid things and hit walls and lash out at people. And when you’re in a leadership position, you can’t do any of that.

Bad stress is the curse of startup leadership. Here are some techniques I’ve worked out over the past 20 years to help turn bad stress back into good stress.

You didn’t become an entrepreneur because you wanted a better job. You became an entrepreneur because you’re on a mission. You might want to make the world a better place. You might want to make lives better. You might just want to find out who you are.

Whatever your mission, just don’t turn that mission into a job.

Chasing a mission is difficult way more often than it is easy — that’s the nature of doing anything worth doing. Being an entrepreneur can be directionless, fruitless, even hopeless at times. We tend to compensate for that by making the mission feel more like a job. We take on responsibilities and create processes and even invent rules for ourselves in an effort to make our dream seem more legitimate. This is especially true when bad stress makes that dream start to feel a little more like a nightmare.

"Your mission has to include an element of fun."

It’s a trap. It’s easy to fall into. Don’t do it.

Your startup is not going to have a better chance of succeeding if everyone comes to work feeling like they have a job to do. You already know this — it’s why you and everyone around you jumped on board.

Bad stress usually means you’ve gone too far to the dark side. Get back on mission.

Again, without knowing the first thing about your particular and unique mission, I can state one fact about it that will always be true: Your mission has to include an element of fun.

I’m not talking about fun like mini-golf or ax throwing. I’m talking about the reasons you started the company in the first place. You didn’t have that epiphany and think, “Well, this will be difficult and stressful and high risk, but at least I’ll have a shitty time doing it.”

Fun gets beaten out of startups pretty quickly by oppressors both internal and external. Investors, customers, board members, employees—hell, even friends and family can suck the fun out of a startup.

Because they all have things they need from you.

It’s hard to have fun when you have expectations, but if you’re not having at least a little fun, you won’t be loose, you won’t be motivated, you’ll do a lot of second-guessing, and you’ll get really conservative with your decisions.

Put some fun back in your startup. This is easy to say but not so easy to do, especially when times get stressful.

It’s hard to say no when you’re an entrepreneur. You say yes to jobs, spec jobs, meetings, phone calls, side projects that could turn into new business, networking opportunities that could turn into new business, and a million other things that may or may not have a material impact on your success. This is not your fault. It’s hard to figure out where that next big win will come from.

It’s hard to say no when you’re a leader. Employees need your time. Customers need your time. Partners need your time. Suppliers need your time. If you’re lucky, investors, board members, and the press might need your time. Local groups need your time. Charities need your time. Your friends and family need your time.

Don’t take any meeting that doesn’t fit the mission. Don’t start any project that doesn’t fit the mission. Don’t create any document or process that doesn’t fit the mission.

And please note that I didn’t say “fit the job” or “fit your startup.” Your mission is what you define it to be. Define it and stick to it. Don’t let the definition flex.

I’m a total task-list guy. I have a personal task list, a mission task list, and a work task list. There’s a lot of crossover there, but you can be damn sure that things like “investor update” are not on my personal or mission task lists.

Two saving graces prevent me from losing my mind at any given time:

1. The task list platforms I use all have a really easy way of pushing any task from today to tomorrow.
2. I’ve come up with the necessary ways of tagging priority to each task on each list, as well as across all three. And I stick to my priorities no matter what.

So, yeah, I don’t care how much revenue is at stake, “kid’s school play” will always win out over “customer call.” Every single time.

I do this because I’m okay with the fact that I’m able to get only so much done today and no more. It’s easy to say, “Be ready to fail,” but no one ever talks about failure in terms of missing your kid’s baseball game versus closing that deal to hit revenue targets for the quarter.

I’m not telling you where to place your priorities. I’m just telling you to respect them.

Leaders have a hard time seeking support from others. Entrepreneurs have a small peer group from which to seek support. Lean on what you’ve got. Your significant other or best friend might not even understand what you do, but they understand you.

You can also seek out posts like this one, as well as groups and individuals who talk about this stuff. And yes, I just plugged myself, and I’m not hiding it, because that’s part of the reason I do this. Even if the topic isn’t on your issue list at the moment, it’s just good to talk, hear, or read shop every once in a while.

Like drinking or gambling, it’s a good idea to recognize when you’ve had too much startup.

I’ve sent people home for the day. I’ve made people take a couple days off. I’ve moved people into new roles when they were falling over from the work and the stress.

Furthermore, much less frequently—in fact, pretty rarely—I’ve done the same for myself. And I still do today. I talk about how rare it is because it’s much easier stepping in to save a friend or co-worker than it is to save yourself.

But a bad-stress, lashing-out you is maybe 10% as effective as the normal you, and you’re probably also sucking the productivity out of those around you. And sometimes you just need some time away to put things in perspective and figure out new solutions.

Make that time part of your job. No—make it part of your mission.

This article was originally published on Medium by Joe Procopio

Joe Procopio is a multi-exit, multi-failure entrepreneur. He is currently the Chief Product Officer at Spiffy, an on-demand vehicle care and maintenance startup. In 2015, he sold Automated Insights to Vista Equity Partners. In 2013, he sold ExitEvent to Capitol Broadcasting. Before that, he built Intrepid Media, the first social network for writers. You can read more and sign up for his newsletter at joeprocopio.com