I have no backup plan. This relaxes me.

Optionality is stressful. It always sounds like it would relieve stress to know you have lots of plans and sub-plans to choose from. But I find instead it just creates existential overhead that makes it harder to be bold, deliberate, decisive, and really bet on myself with abandon.

I’ve written before how desire for options can blind you to opportunities.

As part of my general don’t do stuff you hate paradigm, I put all the focus on removing bullshit and negative activities that make me feel less alive, and don’t really worry about the details of what’s left over. If I don’t hate it and it doesn’t make me less free, go for it. Over time this gets easier as the list of stuff I hate grows with self-knowledge.

I sort of hate goals, but I sort of have some too. They’re more like big giant directional life goals. I want to live free. I want to make other people free. I want to help people discover and do what makes them come alive. I want to help launch 10 million careers by 2024. That last one is as close as I get to concrete, mid-term goal-setting.

I had a great conversation with Marvin Liao from 500Startups recently. He said every year he assesses the previous year, thinks about if he liked what he did, and thinks about what he wants to do for the next year. Then he does it. That’s it. He doesn’t worry about what that next year might parlay into five years down the line. He just takes the best opportunity available for the year ahead.

Turns out I’ve kind of done that same thing, on almost the exact same time frame (I’ve made a few 6 month decisions, and a few two year decisions, but I almost always think in year chunks). I liked the way Marvin approached it with some deliberate reflection. I’m going to add that to my mix.

I had another conversation last week too, about how to find product-market fit with a startup. I think product-market fit is a great way to think of your own career journey too. The guy I was talking to has done this dozens of times and is a shrewd startup thinker. You might expect him to have developed a twelve-step blueprint to PMF in his decades of experience. Instead, he said, “I’m a big fan of just stepping into the unknown and trying to get lucky.”

He described his preferred process as a reverse timeline. You look at your runway and see how long you have to try stuff. In your career, this might be something like an honest assessment of how long you can afford to make little or no money, or how long you can handle not having a clear role or city to live in etc. Say it’s a year. You work in two week increments. You’ve got 24 cycles to test stuff and find happy accidents.

The two week increments are focused and deliberate, and you pay careful attention to the feedback. But you don’t think about something 2 or 10 years ahead, or even more than the next two week increment. You pick an assumption you’re making about your product and/or your market, starting with the most fundemental, and you spend two weeks putting in the minimal effort and risk to find out if that assumption holds. Take in the feedback, adjust, on to the next assumption.

Two weeks is probably too fast for your personal career journey, but something like this might work well. You don’t know when you begin what your product is. What do you offer the world that they want to buy? Or what your market is. What people in what industries value your unique skillset and at what price? So you try some stuff out.

You can do all of this while you have a day job to pay the bills. You could wait tables while you take a month to test out whether people value your writing. Blog every day, see if you can get anyone to read anything you post. Submit a few of the best to third parties. Maybe you get readers. Maybe next you could spend a month testing whether someone would be willing to pay you something for your writing.

The process should be fun. It’s open-ended, but directional. You have a North Star, but you don’t have a specific course to get there, just one segment at a time.

The analogy of you as a startup is a really good one. Take some time to learn a bit about the world of startups, how they try to go from idea to first version of a product, to first traction with customers, to revenue, to potential investment, to scale-ability, etc. Think about leverage, MVPs, entry points that are small but expandable, etc.