Success Is Not a Straight Line for Creative Entrepreneurs

I think some people read these weekly insight pieces primarily because they feel like someone understands them. We all want to belong to something, which usually requires that we also be understood.

Parents want their kids to understand…some day…how much work went into being a parent. Bosses want their employees…some day…to understand how difficult it was to make some of those decisions that weren’t terribly popular.

If you’re on this email list, you are probably running a firm in the creative space and I’ll bet that I understand you a bit. I’m going to assume that’s true and tell you why you probably deserve to be applauded for what you’ve accomplished.

I’m not here to gladhand you, though, because there are probably some ugly truths about who you are. You’re probably less patient than you should be, more resentful when people take you for granted, a bit too wigged out when something slips through the cracks and surprises you, and certainly guilty of a lot of bad decisions.

But generally speaking, I believe you’ve earned the right to be here and I want to explain why I think so:

1. You have picked the trends up a little bit ahead of most everyone else. Because you are widely read, this is actually quite a feat, because the S/N ratio is ridiculous. So sorting through all that stuff is a huge task, but over and over again you’ve put your finger on culture and seen where they were headed a bit ahead of the rest of us.
2. You’ve mastered this ability to not overreact or underreact to what life delivers at your firm’s doorstep. Someone said (that’s what you say when you don’t want to look it up) that things are never as good…or as bad…as they seem. I think that’s true. After a huge client win, while everyone else is still celebrating in the conference room, you’re plotting how you’re going to replace that new client when they leave. Or when an employee commits suicide by jumping out of the second floor, or when the principal dies of a heart attack, or when the number two employee turns out to be a total fraud who’s holding down another job concurrently, or when your CFO burns the agency down to hide embezzling, well, you just keep trucking. (All those things, and many more, are real stories from my client base.)
3. You’ve consistently made principle-driven decisions on the big issues, hanging onto what you believe and not what will make you look successful to your peers and community. This shows up when you fire that talented @sshole with significant client repercussions, dismiss the client who is abusing your account managers, hang onto a struggling employee who would face a setback if you fired them at that moment, or said “no” when someone wants you to be a pawn in their corporate political game.
4. Time and again you’ve slammed your imposter syndrome to the mat until it said “uncle” while you reached further and further ahead to build your skills and enlarge your connections. You’ve led the charge with as much confidence as you can muster, and then given the credit to employees when you won a big piece of business you had no business even pitching. Today I sent an email to a famous economist as if I actually knew the guy! About 99 out of 100 of those attempts I make land with a thud, but hope springs eternal, as it does in the heart of every entrepreneur.
5. You have embraced change, time and again, when those around you are just flat exhausted from your constant meddling with success. As soon as everyone gets comfortable, you start asking the annoying questions all over again. “Okay, but shouldn’t we start offering X to our clients?” Your team loves it when you go on vacation, but dreads every return because on Monday morning there will be “the next big thing” you read about on the beach. I say keep driving them crazy!

You’re sort of like a PAC-MAN character people get tired of. When you aren’t looking, they sneak around to the back of the machine and unplug it…but it just keeps running like the zombie who won’t die.

Do you find yourself in one of those better moments when everything seems to be going your way? Start thinking about what could go wrong and leave the celebration to do some long-term planning.

Do you find yourself in one of those tough times where nothing seems to be going right? That’s okay. You’ve been here before. Don’t succumb to the current pressures. Keep making principled decisions. That’s why you (used to) make the big bucks.

Do you wish you were a bit more appreciated and understood? Well, I can’t help you there. Live with yourself a little better and don’t do needy things or try too hard. The truth always surfaces; it’s like an inner tube that your enemies can’t hold under the water forever. Eventually they’ll get tired and it’ll come flying to the surface.

To be clear, I’m not in charge of whether you deserve to be here or not, okay? But I do know that most of what you’re going to read today isn’t going to resonate with you, it probably won’t change your life, and overall it’s going to be a pretty unremarkable day.

Except that I hope you’ll take some appropriate pride in what you’ve accomplished, even if most people around you have no clue what your life is really like.

How about if we flip this around. Do you know a peer who could maybe use a little encouragement in their leadership role at the moment? Reach out to them and explain how you might understand them and see where it goes from there.

Now get back to work. Tonight I’m renting a big excavator to eradicate three big trees that are standing in the way of progress. If you never hear from me again, it’ll be because I didn’t RTFM.