It Sucks to Grow Up (but Everybody Does)

Truly entrepreneurial people are usually pretty action-oriented. Sometimes I meet rich people who describe themselves as entrepreneurs, and it’s immediately apparent that they’re pretty averse to doing any actual work. I know this because (except for the being rich part) I’m kind of like that. I’ve actually had to build up an alternative work personality that’s extremely production oriented to combat my own navel-gazing strategic dithering, so I totally understand where these people came from.

(Side note — about five or six years ago, my productivity-oriented work personality then doubled back on me and started taking over my hobbies and personal life, which was unexpected to say the least. I think this is how a lot of parents become uncool.)

But basically, if you somehow manage to scrape together a functional business from nothing (and no, not some bullshit consulting vanity project) with a product or service, and paying customers who yell at you when you do something stupid, odds are you’ve had to do a lot of things. If you’re in any kind of innovative or competitive space, you’ve probably had to do a lot of these things very quickly — more quickly than you would have liked, with results that, while impressive in a vacuum, could have and probably should have been better with a little more time.

All of this is okay. Chances are, you simply did the math, looked at your options, and made a bunch of very ordinary, very necessary sacrifices to survive a competitive market.

You are a 2 year old german shepherd

Here’s the problem — once this approach to putting something together from scratch is successful (as it has been at some key point in the life of most new ventures), it often hardens into a religion about how to solve business and product problems, especially if you’re like, twenty five years old and this is (a) your first rodeo, and (b) something you are personally and emotionally invested in.

In this scenario, you’re probably a little like the german shepherd puppy my friend and his wife got a couple years ago. The dog was adorable, and my friend used to chase her around the table in their little apartment, in a big, dumb, cute circle until she collapsed on the floor for belly rubs.

Over the next two years, she got too big for the apartment. But every time I went over there, she’d try to play the run-around-the-table game, even though she was so big she could barely squeeze through the side by the wall, and her giant tail would constantly whack into the lamp and almost knock it over. She didn’t care. The game had proven it’s awesomeness at a critical juncture in her life, and no amount of lamp breaking and wall banging was going to change that.

The point is, if your company is growing as fast as my buddy’s dog, the most effective way to generate the results/progress you want is going to change. And — this is the important part — it’s not just the actual activities that will change. It’s the very process of figuring out what those activities are, and the very process of executing them.

This isn’t because “it’s grown-up time” or some business-cultural nonsense like that, either; just think about the dog again for a minute. It wasn’t “time for her to act her age”. It was time to get a bigger apartment, and probably time to stop trying to get exercise by running in circles around a table that’s barely bigger than you are. These weren’t problems of age or appearance; they were problems of size, nature, and the logistics of getting the results you want.

When a company grows, you are going to start doing more things by committee, which is annoying, frustrating, and inefficient. It’s also completely necessary in the vast majority of cases, because most lucrative opportunities to build something are really complicated — if they weren’t, any lazy idiot who likes money could just go do it by themselves. Ventures like Instagram throw off the calculus for everyone (“let’s make something worth $2 billion that has 12 employees!”), because they rely on a bunch of dependencies other businesses either don’t want or can’t have. Do you have the patience, resources, and cojones to build a product with no revenue until someone swoops you up? Does that someone even exist? If not, you can’t be Instagram. And if you’re not Instagram, you’re going to have to build value the old fashioned way — by doing difficult things that require a lot of hard work from a bunch of people who disagree on lots of things, which by comparison feels like herding cats.

Complaining that this is frustrating, or that it was “better” before, when you could “just do things”, is like an eighth grader complaining about how he wishes school could be like kindergarten again, when he got to play with blocks and go home at lunch. Well, guess what? Kindergarten is only there so you can build more advanced things on top of it — as a member of society, you — like your interesting, unprofitable, mid-stage startup — have basically no value while you’re in kindergarten. You have to go through the whole process, learn from it, and adapt before you’re of any use to anybody. It seems obvious with people, but maybe we wouldn’t feel this way if we gave five year olds valuations based on their future earnings, and labeled some of them “unicorns”.

Bottom line — if you don’t have the stomach to suppress your need for immediate executive gratification in everything from marketing campaigns to product development, you probably don’t have the stomach to build a big, valuable company. At some point, your desire for action devolves into a childish need to feel productive and important. At a strategic or leadership level, that’s not an engine for your business — it’s an anchor.

“But Growing Up Is For LOSERS!!!”

I can already feel the dismissive scorn from mid-stage startup founders towards this argument. After all, what do I know? I’m just some freaking guy who hasn’t started anything. The only startup I was really on the ground for failed, in no small part due to my hesitance to inflate the importance and readiness of unfinished products, or do things before they (or we) were ready to do them with any level of competence. I’ve worked for other really cool early and mid-stage companies, but I’ve neither brought them to life from nothing, or dragged them across the finish line to permanence or acquisition.

But that doesn’t mean I’m wrong here. To return to my last metaphor, I remember being in eighth grade. I thought I was smarter than my teachers, and it’s entirely possible that I was right by at least some measure (after all, lots of eighth graders are probably smarter than I am today). I already knew how to do lots of things they didn’t learn until they got into college, and a number of other things they would literally never understand (“wait, what’s the difference between disk space and RAM again?”). But you know what they knew, that I was completely clueless about? How to get out of eighth grade.

NOBODY knows how to get out of eighth grade better than eighth grade teachers, no matter how smart or accomplished (or not) they are. And until my little arrogant self, with my 5th grade achievement tests and 6th grade writing awards, came to realize that, I was going to struggle. Some kids never do, and it keeps a lot of them from ever capitalizing on all that self-important promise.

Objectively, I didn’t learn that much when I was in eighth grade. The most important thing I did learn was that life was more complicated now, with a ton of factors and repercussions that I’d never considered before but could no longer ignore. That, and that I had to adapt to all of them if I wanted to do anything worthwhile in life. I have a feeling that my teachers would all be very happy if they knew that got through to me, regardless of how poorly I retained the literary symbolism of The Lord of The Flies.

Activity VS. Productivity

So think of me as your business’ eighth grade teacher for a minute. I know — you don’t want to be like me, I keep telling you to think about boring things that don’t seem important, you’re convinced I’m actually kind of dumb, and I wear stupid shirts and make dated references. That’s all fine, so long as you learn one thing from me that I actually know, and then go on your merry way, connecting Snapchat to Waze and somehow raising $200 million to monetize the transaction data.

Here’s my one thing. Activity is not productivity.

To make progress in anything, from building a band to hitting a layup to just getting your Sunday afternoon together, you need strong, decisive moves. You can’t make strong moves if you’re making a thousand different ones, and you can’t make decisive ones if you’re distracted by a shiny object halfway through it. “Holy crap, I have a great idea!” is still a valuable thought — it’s just not the beginning of a real, productive, executable action plan anymore, so you have to stop thinking and acting like it is. Again, if you don’t want to live in a world like that, it’s okay — but you probably can’t build a valuable company unless you’re willing to.

If you are, here’s what to do. Think. Stop. Breathe. Ponder who would execute your idea, and talk to them to better understand what it would really entail. Compare it to what you’re already doing. Contemplate switching costs. Figure out if you really like your idea, or just something about your idea that your company could do through an existing activity. Be open to the possibility that your idea is terrible, infinitely more complex than you realize, or motivated by an irrelevant conversation you had with some other CEO, or some investor who was just babbling and never considers any of this. Do not respond to obstacles presented with “we need to think bigger” (everyone is probably thinking big, they just may have a better grasp of what big ideas require than you do), or “all I’m saying is…” when that’s not all you’re saying. When you want to move fast and break things, ask yourself — whose things are you breaking? Who is going to clean them up, and what important things are they going to have to stop doing in order to do it?

You don’t have to turn into Oracle (in fact, please don’t, one is enough). You don’t have to have subcommittees and use terrible enterprise intranets and resent your customers and become everything we all hate about large, financially successful companies. You just have to challenge yourself to honestly assess what’s going on around you every day, and be ready to accept the fact that if you’re doing your job well, it’s often going to be different than it used to be. And this is a good thing, provided you steer into it and not reflexively away from it and into a ditch.

If you can do that, I swear to God, you really can run a company, and focus on non-self-inflicted challenges, like technology, business development, building great products and good stuff like that. I wouldn’t love working for such crazy companies as much as I do if I didn’t really believe it.