What your boss will not tell you

Five unwritten rules about your career

“I love the thing and I hate it at the same time. The reason I love it is that it gives me so much power. And the reason I hate it is that it has so much power over me.”

The quote refers to smartphones, yet the same can be said for our jobs. It’s at the root of our Sunday Scaries. But it doesn’t have to be this way!

There are some unwritten rules that your boss is unlikely to ever tell you. For starters, what it takes to get your career off the ground is not what will keep you fulfilled. You need to shift gears at every step.

Let’s start from the beginning.

Getting picked

How do you get a shot when you have no experience? This is the first dilemma everyone faces.

Here’s the uncomfortable truth: nobody ever says: “I want to make a risky hire with limited to no experience.” If you’re a diamond in the rough, you need to do everything you can to be cut, polished, and sized for the opportunity.

I used a combination of intense interview prep, doing the job unofficially and saying yes to pretty much everything to become a consultant and later PM.

When you have no track record, you need to lean on high enthusiasm and coachability — leading indicators of potential. Also helps to know people on the inside who can vouch for you. Your potential is your currency.

In short, groom yourself to be an attractive pick, and don’t be too picky.

Doing the picking

Exploration is the only way to figure out who you are. It helps to start at a company that’s friendly towards that either by design (rotational programs, consulting) or by necessity (startups).

Ideally, you’re surrounded by people who have the skills you want to develop. Those who are closer to you in age, ironically, are often in a better position to guide you — there’s a deeper sense of empathy if they remember being in your shoes.

To escape the low-autonomy treadmill, you need to gain valuable and specific skills.
These tend to be revenue-generating: design, sales, writing, coding, etc. Once you get better with practice, the game changes. Your options grow, and you begin to have the opportunity to do the picking. This is a fun, heady time, but also easy to stumble.

When you have multiple companies chasing you, it’s tempting to pick the one that is best at marketing, not necessarily at retention. And sometimes a brand name is too hard to resist.

I’ve been there, and in hindsight, I say just scratch the itch. If you want nothing more than to check the box, do it quickly. Get a taste. Celebrate the win. Then brace yourself... because once the novelty wears off, you will be left feeling hollow and disappointed. So what next?

Right pond, right time

We like to attribute success to individuals. But reality is an interaction of individuals and their environments. You need both to align.

As you hone your signature strengths, picking the right pond becomes more important. You want to be in a place where your strengths are highly valued, and where the DNA matches yours. There are plenty of capable people who get organ-rejected by companies because of a culture clash.

A company does deep research on you, why wouldn’t you do the same? You used to get rewarded for saying yes, but disproportionate rewards now come from saying no.

Get clear on how decisions are made, figure out the profiles who thrive vs. flounder, and talk to some former employees to get the unfiltered truth. Some examples of questions to ask, inspired by this post:

  • What were the last few things you launched? How did you decide them?
  • What was the last feature you killed? How did you decide?
  • What have you learned about your customers? How did you learn it?
  • What separates the people who thrive vs. flounder here? Can you share examples?

You also need to ask yourself some questions:

  • Take a hard look at who you’re working with. You are going to become a version of them. Are you ok with that?
  • How does the work you’re being hired for fit into the company’s portfolio?
  • How much visibility and scrutiny will you receive?
  • What is the ceiling for growth? Are you excited by it?

Same questions apply once you’re on the inside and evaluating whether to stay or go.

As you gain more career capital, the script flips. The prize is a lot of quality options. The price of freedom is picking the right options to continue growing.

Going off-menu

Sometimes the best option is not even on the menu. After all, the menu only covers what’s in-season and has been done repeatedly. The brilliance of the internet is that you can learn and do pretty much anything without permission.

You can create your own options.
Or as Tim Urban would say, become a chef.

This is a major mindset shift, especially if you’ve been a cook following recipes your whole life. It requires asking: what do you want?

For example, you become like the people you spend the most time with. Your natural defaults are coworkers, family, peers from school. But you can pick your own team!

You can get access to people at the top of their game through books, podcasts, Twitter, and more. You’re not bound to your local pond anymore.

One of my fears quitting my job was that I would be cut off from smart people. But I’ve been blown away by the caliber of people I get to learn from everyday. I’m sourcing globally.

Growth vs. “enough”

You can get pretty far by blindly following the social script, but you’ll never feel fulfilled until you get real about what you actually want, independent of others.

You need a personal compass for success, not a yardstick inherited from family and friends. Here’s the good news: having a personal compass is not something you’re born with. It’s discovered through trial and error, and evolves over time. No matter where you are, you’ve already started.

It took me nearly three decades to realize that every goal I ever set was for social approval. A prestigious job, The Most Important Project, early promotion. I made the “right” moves, yet was consistently left wondering: is this it?!

I thought success was reaching ambitious goalposts, but here’s the thing: the goalposts never stop resetting. This is why jobs can make you feel powerful when things are going your way, but can just as easily make you feel powerless when the tide turns.

Growth at all costs is a flawed strategy. To be fulfilled, you need an appreciation for “enough”.
Where you draw that line is up to you.

Ultimate prize

True success comes down to closing the gap between who you are and where you choose to be. It’s not defined by your boss, it’s defined by you. Consider this: even if you have a job, you’re actually an entrepreneur. The only difference is you have one customer. Choose wisely.

We spend most of our waking hours plugging away at work. While the first order of operation is to create value for others, the only way to do it sustainably is to choose meaningful projects.

Learn valuable skills, then deploy them in ways that are important to you.
The ultimate prize for all the hard work is getting to know yourself, and making and creating choices that allow you to live the life you want.

These decisions are tough. Feel free to reach out if you have questions!

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One last thing: I made an actionable toolkit to grow your product career! Get the shortcuts that took me years of work to figure out.

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