Ira Glass, the creator of the radio program This American Life, has this famous quote that’s worth reading in its entirety:
“Nobody tells this to people who are beginners, I wish someone told me. All of us who do creative work, we get into it because we have good taste. But there is this gap. For the first couple years you make stuff, it’s just not that good. It’s trying to be good, it has potential, but it’s not. But your taste, the thing that got you into the game, is still killer. And your taste is why your work disappoints you. A lot of people never get past this phase, they quit. Most people I know who do interesting, creative work went through years of this. We know our work doesn’t have this special thing that we want it to have. We all go through this. And if you are just starting out or you are still in this phase, you gotta know its normal and the most important thing you can do is do a lot of work. Put yourself on a deadline so that every week you will finish one story. It is only by going through a volume of work that you will close that gap, and your work will be as good as your ambitions. And I took longer to figure out how to do this than anyone I’ve ever met. It’s gonna take awhile. It’s normal to take awhile. You’ve just gotta fight your way through.”
It’s such a useful insight for creative work. It’s also a broader lesson that the thing that will be your ultimate strength can be, during a transition phase, a weakness that you have to overcome. Having great taste is ultimately something that will make your work great, but in the short-term, when you are beginning to learn a craft, that same taste tells you that your work is worthless. Your taste makes it hard to persevere through the practice and master the craft to a level a worthy of your own taste. To make it through that phase, you have to let some bad work happen—your own—and have faith that the process will improve it over time.
Something similar happens often when making the transition from a maker to a manager. Credit to Paul Graham for pointing out some important differences between makers and managers in the modern workplace. Although in this instance I’m not talking about scheduling, but taste or something like it.
Most of the people I know who are now managers, didn’t go to business school and train to be a manager, they started as makers. They started as founders, doing all the making at a company they created from nothing, or they started as key individual contributors, the first marketer/designer/developer at a small organization. Over time the organization grows, to hit its goals it needs a design team and an engineering team, and so talented individual contributors start hiring, resourcing, planning and managing.
And here is the most important skill I know for making this transition smoothly and effectively:
Let bad work happen.
In many situations, when you’re hiring the first few people to join your team, you’re hiring people who are not as “good” as you at the job. “Good” can be defined a lot of different ways: efficient, fast, thorough, creative, etc. Life situations can determine a lot this, so it’s not universal, but often your fourth engineer is not going to be as talented as the technical co-founder who wrote your entire first v1 single-handedly. Maybe they will be there one day, but if they were already there, they would probably be a technical co-founder somewhere else.
Aside: My experience is mostly with bootstrapped companies and now nonprofits, but generally you have to hire people and train them up. I often hear entrepreneurs talk about how they only hire people who are better/smarter/more-talented than they are but I’ve never understood how that works in practice. Maybe it works for funded companies, but in my experience, when you’re at the stage that you need those people is exactly the time when you can’t afford them.
Again, not always, but it’s a common enough occurrence that people transitioning from maker (high performing individual contributor) to manager (building a team) are managing people with less individual skill or self-direction. Or at least that will be how they perceive it. The biggest mistake I’ve made, and seen others make, in this phase is to micro-manage the work of their team, trying to get everything up to their own personal performance level.
It’s critical to:
- Let work ship that isn’t up to the same exacting standards you have for yourself. They need to get real feedback from the world, not just from you.
- Avoid “stage-gating” their work, sending it back for improvements endlessly before allowing it to be finished. Provide ongoing feedback and guidance while building up a momentum of progress.
- Let your team take 2x, 5x, 10x longer to figure out a solution you could bash out in an hour. They need to build those problem-solving muscles to get faster.
It’s important to acknowledge that eventually the leverage of a well functioning, high performing team will surpass anything you could individually accomplish. Letting some “bad” work happen is how you fight through the transition phase. Eventually, your individual skills will be what makes your team truly great, but in the short term, you have to fight your instincts to push through the transition phase.