Jeannie Sullivan
Essays Collection Gatherings About
On Work · 4 min read

Two Kinds of Stuck

For years I believed I was a terrible procrastinator.

Once in college I tried doing it the right way. I went to the library early. I made an outline. I wrote a first draft and then a second. I made a C.

So I went back to writing my papers the night before they were due, and I made A's. I didn't tell anyone, because it felt like cheating. It took me years and somebody else's book to understand that I wasn't procrastinating. I'm a sprinter. The pressure creates the clarity, and the ideas assemble themselves while I'm doing something else entirely.

Here is the part I think about now. For all those years I was solving the wrong problem. I thought I had a gap: I don't know how to work properly, somebody should teach me. What I actually had was a pattern, and the pattern turned out to be a strength the moment I stopped fighting it.

The C wasn't the expensive part. The guilt was.

Two kinds of stuck

I see this constantly in the work now, and it took me a while to name it. There are two completely different reasons a capable person stops moving, and they feel identical from the inside.

The first is a gap. There is something you don't know, and someone could teach it to you in an afternoon. How to price a proposal. How to set up the email sequence. What a term sheet actually says. This kind of stuck is boring and mechanical and enormously common, and it responds beautifully to being taught.

The second is a pattern. You already know what to do. You have known for months. You are not doing it, and the reason lives somewhere underneath the task, in a belief about what it would mean about you, or a habit built so long ago you no longer see it as a choice.

Neither one is better or more sophisticated than the other. But they need opposite things, and choosing wrong is frustrating in a specific way: you do the work, you finish the thing you bought, and nothing moves.

The question that separates them

Here it is, and it takes about two seconds to answer honestly.

If someone handed you the answer right now, would you do it?

If yes, you have a gap. Go find the person who knows, pay them for an hour, and get on with your life. Don't dress it up as a journey.

If you flinched even slightly, that's a pattern. And no amount of information is going to touch it, which is why the last three books you bought on the subject didn't help. You didn't need the information. You already had it.

Why we almost always guess wrong in the same direction

We reach for information. Nearly every time. Not because we're foolish, but because information is *buyable*. There is a course, a book, a webinar, a template. You can purchase it this afternoon and feel like you've made progress before dinner.

Looking at the pattern requires something much less comfortable: sitting with somebody who asks you questions you have been carefully not asking yourself. Nobody has ever felt productive in the first ten minutes of that conversation.

So we buy the course. A course is much easier to purchase than a mirror.

It happens the other way too, and when it does I try to say so quickly. Someone books a session with me, we talk for twenty minutes, and it becomes clear that they don't need coaching at all. They need to be shown how to do a specific thing, once, by somebody who has done it. That is not a failure of the conversation. It's the best possible outcome of one, and it's cheaper than what they came prepared to spend.

What to do with this

Take the thing you're stuck on right now, the one that came to mind in the first paragraph. Ask the question. Would you do it if someone handed you the answer?

Then buy the thing that matches. A tutorial for a gap. A conversation for a pattern. And if the honest answer is that you've been buying tutorials for a pattern for two years, that's not a character flaw either. That's just the first accurate diagnosis you've made about it, which is genuinely where everything starts.

I spent years thinking I needed a better process. What I needed was permission to use my own.

If you want to look at this more carefully, two kinds of stuck walks through three real situations where the same request had two completely different roots.

Read another
On Work · 4 min read

The Far End of What You're Good At

Ask someone which failure sounds most like them and they answer in under two seconds. Nobody has to think about it, which tells you something.

Story · 3 min read

Rest On Your Bike

On a hot afternoon in the South Carolina foothills, my husband told me to rest on my bike. It took me twenty years to understand what he meant.

Notes

Every so often I write one of these before it is finished, and send it to whoever wants it.

No schedule, no pitch. An invitation, something worth passing along, or a question I have been asking myself that day.

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