Running on Should
You didn't start a company because it was the right thing to do, or the responsible thing. You did it because you wanted it. You wanted it badly enough to do it despite the difficulty and the risk.
That want is not a little thing. Every founder starts with it. Few know what it's worth. They believe building something great is mostly a matter of committing to unpleasant, grueling work. They're half right. Building a company takes grit, but grit alone has never built one. The want is the one thing you can't build without. It's also remarkably easy to lose.
I work with a founder who's in his first couple of years of building his company. A few months ago he brought in an outside advisor to help him build a two-year plan. The plan was good. It had a mission, a funnel, a list of programs. He walked me through it, then stopped. "It all sounds right," he said. "I just don't know."
In the months he'd had it, he hadn't used the plan to make a single decision. He blamed himself for a lack of discipline. If he could just stick to it, focus on the things he should be doing, he'd be in a better place.
Laziness wasn't the issue. The plan wasn't bad either, it just wasn't built around what had excited him in the first place. He had started his company because he wanted to create something specific. Now he was trying to run that company on a list of obligations. His plan was made up of shoulds, not wants.
Should is seductive. When there's no longer anyone above you, and every decision and consequence lands on you, part of you wants to be told what to do. We should have raised a Series A by now. I should be posting on LinkedIn every day. We should have a COO. Should sounds responsible and objective. Check the right boxes and you'll end up with the right company. But it rarely gets you the great thing you imagined, because it’s not yours.
Obligations feel objective because they are borrowed from something outside of you: an advisor, a board, a founder you follow, the company you keep comparing yourself to. This also means they have nothing to do with the thing you wanted to build.
There may be a good reason behind each obligation, but it isn't yours. We should have raised a Series A by now because that's what companies our age do. We should hire a VP of Sales because every company our size has one. I should send monthly investor updates because that's what good founders do.
My own version of this was headcount. At one company, the board wanted us to go from 40 people to 160, because that's what a venture-backed company at our stage was supposed to look like. I didn't want 160 people. I did it anyway, and for the next year I ran a company that was four times bigger and no more mine.
When you run on obligation, you're building through grit alone, with none of the energy that comes from wanting something. The difficulty of this can be deceptive. When you're straining, it feels like you're doing something important. It hurts, so it must be work. I'm struggling, so it must be getting me somewhere. But strain doesn’t necessarily mean you’re working hard. It often means the work has come loose from the want.
Working like that, you can survive for a while. You just can't go anywhere. The company keeps the lights on, but nothing pulls it forward. Then things get hard. A deal slips or a key hire walks, and that's when should fails you completely. Right when you need to push hardest, you find you have nothing to push with. It's hard to fight for something you don't believe in.
Building on want doesn’t mean you only do the work that seems fun. There’s plenty of work ahead of you that you won’t want to do, and you’ll do it anyway. You don’t have to want every individual task, as long as you want what it gets you. You make the cold calls because you want the customers. You sit through board prep because you want the board on your side when it matters. The task is no longer an obligation. It’s a step toward the thing you want.
This was the work the founder had to do. He needed to rewrite his plan around his original drive, not the idea of what a company like his should look like. We set the document aside, and I asked what he wanted in the next twelve months. He didn't start with a number. He started with the work. What he wanted most was to put his own creative work out into the world, and he didn't want to share it with a handful of people. That was what had kept him stuck for months: an audience too small for the work he cared about.
I asked how big the audience needed to be. He had 600 people and wanted 3,000 within a year. His whole voice changed saying it. Three thousand was the size of audience the work deserved.
Now every item in his plan had something to answer to. Would more social content get him to 3,000? Would a new program? The plan stopped being a list of what a business like his was supposed to do and became his road to the thing he wanted. Growing a list five times over in a year is slow, hard work. Nobody gets through a year of that on a should.
Try this with the plan you're running this quarter. Read it out loud, and put "I want to" in front of every line.
In your head, the difference between should and want isn't always clear. Said out loud, you can usually feel it in your body. We should have a COO by the end of the year becomes I want a COO by the end of the year.
Did it sound true? Then it's yours. Keep it. If it went hollow in your mouth, it's not a want. That doesn't mean you drop it. It may still be the right move, but it has to be reconnected to the thing you want to build. So finish the sentence with "because," and listen to whose voice the reason comes out in. I should send monthly investor updates because that's what good founders do is someone else's reason. I should send monthly investor updates because I want my investors to trust me when things get hard is yours.
Now you can see what the obligation is for. That lets you choose the best way to get there. Maybe that's still a monthly update. Maybe it's a quarterly call, plus a phone call the day something breaks. Either way, you're no longer completing a duty.
If you can't find a want anywhere underneath a should, if every because comes out in someone else's voice, that's your permission to drop it.
Saying what you want out loud does one more thing. It tells you what's in your way.
I once asked a leader I coach to start each morning by writing down a few things he loves about himself. When he tried it out loud with me, he tripped over his own sentence. "Things I love about myself. Or should love." He heard it as he said it, stopped, and tried again. "I want to love things about myself, but I don't."
That but is the most useful word in the sentence. It names what's standing between you and what you want. A should can only be obeyed or missed. When you miss it, all it tells you is that you fell short. So you try harder at the same thing. When you say what you want out loud, and you're honest, you usually hear why you don't have it yet.
In a business, it sounds like this. I should hire a VP of Sales keeps you reposting the same job and wondering why no one sticks. I want to hire a VP of Sales, but I don't trust anyone else in front of my biggest customers tells you what the plan actually has to solve. It isn't a hiring problem. It's a trust problem, and trust is something you can build.
Commitment and discipline both matter. They just aren't enough. Want is what lets you attempt something that looks impossible from the outside. It's what carries you through a brutal quarter and the months when nothing is working yet. Nobody told you that you should start this company. You wanted it, and you did it despite plenty of reasons not to. That drive got you here. Don't run the company on something else.
Read your plan out loud with "I want to" in front of it. Then tell me which line went hollow, and whose reason was behind it. Reply or comment. I read every one.
—Christine
If you want to go deeper
Here's where to start:
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⚫️ The 20 Hour CEO Self-Paced Course: The frameworks, systems, and playbooks to stop being the bottleneck — on your schedule.
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