On Being a Happy Entrepreneur
How can you do this entrepreneurship thing and stay happy at the same time?
Happiness is pretty straightforward - it’s the distance between expectations and reality. If you forced me to make an emoji-based graph on it, it’d look like this:
Humans stink at this in their normal lives and really stink at this as entrepreneurs. We stink at this as entrepreneurs for three big reasons:
External Signals: Our friends and family will outwardly say or inwardly hint that what we’re doing isn’t a great idea. They’re mostly just projecting their insecurity - they need to say your life choice is a bad one to affirm their life choice of not doing something “risky” is a good one. But, when you’re on the other side of that it’s nearly impossible to suss it out, so the external signals of “this is probably a bad idea” permeate.
The General Opaqueness of Entrepreneurship: Who the heck knows if we’re doing a good job? You got 65 signups to your landing page. Is that good? Does that mean the business will be a success? The rest of the world has very clear steps on their ladder. You’re an analyst and you get promoted to associate and that’s great. In our world, you’re CEO from day 1 and that plus $2.50 will get you on a subway. It’s tough to know if things are going well and harder to project it. That’s why people pay (yes, they’re paid) to get on Forbes 30 under 30 or Fast Company’s Most Innovative list - there’s nothing else to grab on to.
The Need to Get People On Board: Despite the opaqueness, we need people excited. We need investors, team members and potential customers to believe the thing we’re building is useful before we’re even sure it is. So, we tell stories about a company that might exist some day.
The confluence of the three create the conditions for a very unhappy person.
To prove to your friends and family you made the right choice, you exaggerate where you’re at. Same thing with investors and customers. You live a few milestones in the future - saying you’ve already achieved the stuff you hopefully will in a few months.
But internally, you have no clue where you are because of the whole opaqueness thing.
So, our emoji graph gets real wonky.
You might say “yeah, we’ve got 1k signups and are having meetings with angel investors” to a friend so that they think you’re doing well. Maybe you’ve only got 360 signups at the time and have gotten one bite from an angel.
The big problem here is that when you do reach 1k signups, you can’t celebrate or get excited because everyone already thinks you did that.
How to be happier
1. Remove (mitigate) exaggerated expectations
This is tough, because to be successful you will have to “live in the future state” with some customers and investors to get them to play ball.
I’ve found the key is a few people internally who you are absurdly honest with. Obviously for you all there’s me, but I’d recommend getting a few others. Then, I’d recommend a journal that is the real source of truth. The place you actually are, the feelings you’re actually having, the wins, the losses- get every bit of it out to clear your conscience each night. Create a blank slate. Create real expectations. That leads us to #2
2. Safeguard and Protect Those Expectations
The graph is real. That’s where happiness comes from. One variable on the graph - expectations - is under your control.
Set yourself up for success.
This doesn’t mean setting a low bar for yourself. It means picking expectations you can meet and measure so that you’ll be happy.
Some suggestions here:
Write them down: Expectations are like most things in life - if you don’t pick them purposefully, someone or something else will. Again, hit that journal.
No numbers, ever: People who say “I want a business with 2mm ARR” set themselves up for a terrible ride. Now, I don’t think it’s a bad exercise to say “what kind of business could I start in a year that could reach 2mm ARR,” because then you have to think “Ok I either need 2 companies paying me a million each, 20 paying me 100k, 200 paying 10k, 2,000 paying 1k, 20,000 paying 100” etc. But don’t judge yourself by them, because of the goal post problem my mom talks about. When I get X podcast downloads one week, I reset the number I want for the following, so I’m never happy. Numbers will never make you happy.
Careful on the To Do list: An odd one, but if you have 700 things on your to do list you’ll obviously never get there. Then, each week you’ll say “ah, got to some of it” and be bummed out. That’s an expectation / reality gap. Be clear on expectations you can meet or exceed everywhere.
Effort and consistency based: Do something each day to move forward then get pumped when you do. Set a 30 day streak to do one positive thing for the business and you’ll be in a FAR better place in 30 days, regardless of what you do. And you can meet that.
It’s important for your baseline to be happy while you do your startup because if you aren’t, when stuff gets tough (and it will), you’ll probably stop.
Also, it’s just better to be happy. Obviously. And the key is expectations — that’s something you can control.