Your career plan is a guess (and that's ok)

Recently stumbled upon this quote from screenwriter William Goldman:

"Nobody knows anything... Not one person in the entire motion picture field knows for a certainty what's going to work. Every time out it's a guess and, if you're lucky, an educated one."

If the people greenlighting USD 200M productions don't know for sure, it's safe to say we don't really know what's going to work for us either. This applies to all aspects of life, but especially to our careers.

In 2018, I became obsessed with Scrum. I thought it was an infinitely better way to manage projects. I became a certified Scrum Master, implemented it in every organization I was part of, and built a nice side hustle teaching sports associations to manage their projects more effectively.

My arch enemy: waterfall planning. You take one step, then the next – but everything is pre-determined. As soon as something unexpected happens, the entire plan falls apart. As Prussian field marshal Helmuth von Moltke put it:

"No plan survives the first enemy contact."

Yet when I speak to second-year business students, this is exactly what they have in mind:

• Get a Bachelor's degree.
• Follow up with a Master's degree in a similar field.
• Get into a renowned management consultancy or investment bank.
• Spend 3-5 years there.
• Shift into management in a corporate.
• Spend the rest of your career there.

It's nice to have a plan. But … what do you do when you realize you actually hate making slides?

The entire plan falls apart.

The old career model – pick a lane and stay in it – doesn't work anymore. You might hate the industry you're in. AI might eat your job. The role you thought was exciting is kinda boring.

We need a new framework.

What if we approached career planning like building a startup?

As a reader of this newsletter, I'm 95% confident you're familiar with The Lean Startup.

In short: build an MVP → measure the performance → learn and adjust → build the next MVP.

Let's map this to career planning:

• MVP → Minimum Viable Experiment. Instead of becoming a product manager, build a small product that solves a problem you have. Don't become a VC; write five deal memos and see if you like it. Do lots of small experiments (side hustles, projects) that act as a proxy for the real thing.
• Build-Measure-Learn → your career loop. Try experiments → see what they do to your energy → adjust. The faster you learn, the better.
• Pivoting → career change. It's okay to pivot if your experiment yielded data — or you discovered something that gives you energy instead of draining it.
• Validated learning > all else. A better title isn't worth anything if you hate your job. Try different things, pursue the ones you enjoy most.

How do we put this into practice?

"A plan is simply a guess you wrote down." — Basecamp founder Jason Fried

Every experiment starts with a hypothesis. You still need a plan; just recognize that the plan might change.

So write down the first hypothesis you want to test.

In my case: I've been obsessed with strength & conditioning coaching for a while. It's something I could see myself doing after my Lacrosse career. (It also has nothing to do with what I do for a living right now.)

My hypothesis: I'd enjoy being an S&C coach.

The "traditional" way to approach this would be to buy a couple of textbooks, invest in a training course, and get certified. Not very lean.

Better: take on 2-3 friends as test clients and coach them for a month. Write programming, understand their goals, go to the gym with them, give feedback. I already know enough about lifting to just do that.

If I hate it at that point, there's no point in getting certified. Back to the drawing board. (Which, btw, would still be a win: within four weeks, I've eliminated something I've thought about for a long time. This opens up new possibilities.)

I see this a lot with content: everybody wants a newsletter or good short-form videos or a podcast; very few people actually do it. It's easy to test: write a few newsletters, record a few reels, publish 5 podcast episodes, see how you like it. This is how I learned that I love writing newsletters and hate editing short-form.

Pick an experiment → write down your hypothesis → commit for a set amount of time → document your learnings → adjust.

Another good way to pick an experiment: dissect the aspects of your job you like and hate.

From 2016 to 2020, I ran a recruiting company, bringing nurses from Italy to Germany and teaching them German. I really liked the recruiting part, but hated that it took forever to generate revenue (we had to teach them German first), was hard to predict, and had below-average margins (language courses are expensive).

With Generalyst, I kept the parts of recruiting I loved – working with people daily, unlocking new opportunities for them, solving one of the most pressing needs companies have: getting the right people on board – and cut the parts I hated: time-to-value is four weeks instead of 9 months, and the margins are much better.

Lastly, you can run these experiments inside your job. If you're already in a generalist position (like Founder's Associate), you'll get your hands dirty in plenty of disciplines. That's why most FAs don't stay FAs: they test many things, then take on a dedicated role doing what they liked most.

Building a career you like is one of the trickiest puzzles of our life. Every career is slightly different, and you can't plan it all upfront.

What you can do: constantly test, learn, and iterate. Eventually, you'll arrive at a career (or a portfolio of activities) that works perfectly for you. And when you get bored, you can always change it again.

So let me ask you: what's the cheapest experiment you could run in the next 30 days on something you're curious about?

To quote my dear friend Allison: "I don't really know anything about anything."

Neither do we. So let's find out as fast as possible.

LFG.

PS: If you're curious about alternative ways to build a career, also check out my Portfolio Career Playbook.

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Whenever you're ready, there are four ways I can help you:

[1] Reclaim up to 4 hours per day and find time to do the things you've always wanted to do by enrolling into Personal Productivity OS.

[2] Hire your next Founder's Associate or other business generalist position with my startup, Generalyst Recruiting.

[3] You could also find your next startup job in Europe by simply applying as a candidate.

[4] Learn how you can build your career as a generalist by subscribing to this newsletter. ⬇️