Four things you can’t learn while running your business


Most entrepreneurs I know are passionate about learning. They believe that they can pretty much pick up most of what they need to know “on the job.”

And for the most part, they're right. They learn to optimize their work efforts, to network better, and to pitch/sell better.

But the assumption that you can learn everything on the job that's required for you to be successful is a fallacy. Right off the top of my head, I can think of four things you won't ever learn while running your business.

The first two are mindsets. The second two are skills.

1. Your defaults will hurt you as much as they'll help you

I've never run a business alone (except when I was five, selling Now & Laters). So I can only speak from the experience of starting small startups with a couple folks. But it's that experience that helped me see this clearly.

We all, every one of us, have blind spots. And we all have defaults – particular “takes” we have on the way things work. They're the stories we tell ourselves – the stories we believe.

And most of the time, the stories help us – they give us what we need to take shortcuts, or to feel empowered or enthusiastic.

But these same defaults can kill everything we're doing. If you're an engineer, I can guess one of yours – “We need more features,” or “the answer is the next cool feature.”

I can't tell you the number of times people have killed their own businesses because they burned too much money building features that weren't solving the core issue that needed to be solved.

How do you mitigate this dynamic? You work in teams. Because it's rare that everyone has the same blind spot. It's rare that everyone has the same defaults.

You won't know you need a team until it's too late. So just take my word for it. Bring a second or third person into the mix so that you can see things from another perspective. Tell them it's their job to find and disabuse you of your blind spots and defaults.

2. Success isn't a product of hard work

This is for my friends that are in their second business. Now before you call me a hater, just remember I've been a part of five startups and had three successful exists (and one is still around today). I learned this the hard way.

But the stories we tell ourselves (and others) goes something like this: “I assembled an amazing team. We all worked really hard. We got traction in the market and people loved our products/services. It took a lot of work but we reached our goals.”

Guess what? Success often requires our hard work, but that's not all that's required. It's necessary but not sufficient. There's chance, luck, environmental, social and political dynamics, along with competitive dynamics all at play.

Most people don't learn this while running their first, or second business. It's only when things aren't as repeatable as we hoped, that we start realizing that the story we were telling ourselves had holes.

How do you fix this? Do you work less? No. Keep working hard. But I'd challenge you to keep building relationships like mad, because you never know what chance relationship will open a door or share an insight that may give you a head start against the competition.

3. Environmental Scanning & Strategy

Here's what I know about most freelancers – they're either sitting around doing nothing, waiting for work, or they're completely packed with no time to spare.

I don't think I've met many “lifestyle” freelancers that have found perfect balance. And I'm not talking about the “4-hour work week” crap that I don't buy.

Am I suggesting that people need to learn balance? Nope. The skill that I don't think people can learn while running their business is called environmental scanning. It's a core part of how I think about strategy, which is why I've bundled them here.

Environmental scanning is the practice of surveying all that is going on around you. Who is doing what, when, and how. It even helps you determine the why.

Some people believe that you should just ignore the competition and do your thing. I have to agree that it's an approach, but not one I'd recommend.

Other people will agree that you should do it, but they're too busy to make it a habitual part of their regular work week. And because of that, they can't think strategically about anything. Because they don't really know the lay of the land.

If you play chess, you know you can't make moves without looking at the whole board, and at what your opponent is doing. You have to take that into account as you plan your next steps.

Do you know the trends when it comes to adoption, attrition, project size, revenue, profit, pain points, and more in your space? Are you following and tracking it?

4. Hustle

I know. You're going to tell me hustle isn't a skill. But I disagree. And I mean if it wasn't rude, I'd write it in all caps. I couldn't disagree more.

I don't care if you got a degree. My first degree was in social welfare. My graduate degree in leadership. Nothing to do with tech.

I don't care if you have tons of experience. I started working with the internet in 1995. Without any technical chops. The rest of the folks that were working on the internet in those days were C programmers. I knew (conceptually) what a pointer was. But only conceptually.

From a business perspective, I never had an MBA. And I was the youngest guy in the room, for over a decade. Without pedigree. Without the experience of my peers.

But I brought one thing no one could take away from me.

While people slept, I worked. While people watched tv, I read. While people took vacations, I worked.

Now, don't get me wrong, I'm not saying you should have no balance and work 18 hours a day, 6 days a week. I would never tell you how to live.

What I can tell you is that watching hours of television, sleeping long days, and looking for the easiest short-cuts to get things done won't be the way to success.

And that's not something you learn while you're working – in whatever way you're working. You either decide that you'll embrace discipline and diligence, or you won't.

But I can promise you this – even if your name is never in lights – here's one thing you'll enjoy.

When your head hits the pillow, you'll sleep well. You'll sleep knowing you added value. You'll sleep knowing you hustled. You'll sleep knowing that hard work and discipline makes up for a lot of mistakes, inexperience, and the lack of a pedigree.

So test. Try. Run. Run harder.

Give it everything. Learn. Ask questions.

Get up after you fall. Get feedback.

Rest. Reflect.

And do it all again tomorrow.