I’m sitting in a Starbucks in 2014—the one on 4th and Seneca in Seattle—staring at a blank Google Doc titled “Career Roadmap.” I was 24. I thought I needed to know exactly where I’d be at 29. I wrote down things like “Senior Project Manager” and “MBA completed.” I spent three hours on it. It felt productive. It was actually just a very expensive way to lie to myself. I felt like a fraud because I didn’t actually want those things, I just thought I was supposed to want them.
The truth is, five-year plans are for people who think the world is static. It isn’t. It’s a mess. Most of the jobs people have now didn’t exist when I was in that Starbucks. Trying to predict your life five years out is like trying to predict the weather in a city you haven’t even moved to yet. It’s a waste of energy.
The part where I admit I was completely wrong
I used to think that if I didn’t have a spreadsheet for my life, I was failing. I looked at people who “drifted” with a mix of pity and suppressed jealousy. I thought structure was the only thing standing between me and total obscurity. I was completely wrong. Structure is often just a cage you build for yourself because you’re afraid of the unknown. What I mean is—actually, let me put it differently. Structure is great for building a bridge, but it’s terrible for discovering a new continent.
In 2017, I was working at a mid-sized logistics firm called GlobalLink. I had followed my “plan” to the letter. I was a “Lead Analyst.” I had the salary. I had the title. And I spent every Tuesday morning in the bathroom stall of the 14th floor crying because I hated the actual day-to-day work. The plan worked, but the life sucked. I had optimized for a version of myself that didn’t exist anymore.
Planning is just high-end procrastination.
The “Hours of Dread” Metric
I started doing something weird after I quit that job. I stopped looking at titles and started looking at my calendar. I started tracking what I call “Hours of Dread.” For 14 months, I kept a tally in a cheap Mead notebook. I hate Moleskine notebooks, by the way. I know everyone in “creative” fields loves them, but the paper is too thin for a decent fountain pen and they’re overpriced for what they are. I’ll take a $2 spiral-bound from CVS any day. Anyway, I tracked every hour I spent doing something that made my stomach sink.
I tested this across three different freelance gigs and one part-time role. I found that 68% of my “dread hours” came from meetings where people used the word “alignment” more than three times. That’s a real number. I tracked it. When I stopped trying to plan my “career” and started trying to minimize that 68%, everything changed. I didn’t need a five-year plan; I needed a “next week shouldn’t suck” plan.
A take that might get me in trouble
I know people will disagree with this, but I think most “career coaches” are just failed middle managers with a Canva subscription. They sell you the illusion of certainty because certainty is a high-margin product. They want you to believe there is a ladder. There isn’t a ladder. It’s more like a messy junk drawer where you eventually find the batteries you need if you rummage around long enough. Most corporate training is just a tax on your sanity designed to make you feel like the company cares about your “growth” while they actually just want you to stay in your seat for another year.
If you’re staying at a job just for the “vesting schedule” but you hate the work, you’re essentially selling your youth for a down payment on a house you’ll be too tired to enjoy. It’s a bad trade. I see people do it at Amazon and Google all the time. They’re miserable, but they’re “vesting.” It’s a golden cage, and the lock is on the inside.
How to actually design things
Instead of a five-year plan, I use a three-pronged approach that feels a lot more human. It doesn’t require a spreadsheet, and it doesn’t require you to know who you’ll be in 2029.
- Optimize for Optionality: If a choice closes doors, it better be for a massive payout. If a choice opens doors, take it even if the pay is slightly lower.
- The Sunday Test: If you feel a pit in your stomach at 4:00 PM on a Sunday, your current “path” is broken. No amount of future “VP” titles will fix that.
- Ignore Slack: This is a personal rule. Slack is a slot machine for anxiety. I refuse to keep it open all day. I don’t care if I miss a “huddle.” If it’s truly urgent, they’ll call. (They never call).
I might be wrong about the Slack thing. Maybe some jobs actually require it. But for me, it was the single biggest drain on my actual productivity. I’ve become much more “successful” by being harder to reach.
The truth about “making it”
I’m still not a VP. I don’t have an MBA. I work on a bunch of different projects, some of which are boring and some of which are great. But I haven’t cried in a bathroom stall in years. My “career” looks like a disaster on paper if you’re looking for a straight line. But it feels like a success when I wake up on a Tuesday and don’t want to hide under the covers. Career design isn’t about the destination. It’s about making sure the vehicle isn’t on fire while you’re driving it.
Do you actually like what you’re doing on a random Tuesday afternoon? If the answer is “no” for three months straight, your five-year plan is just a suicide pact with a future version of yourself. Burn it. Start over. Focus on the next six months. That’s plenty.
What’s the one thing you’re doing right now just because you think you “should”?