What to do when you feel like you should know everything [#63]

“Hiring for a senior marketing manager – 3-5 years of experience.”

“COO for a scale-up – 5+ years of experience.” 

“Head of Sales in startup – 5+ years of sales experience.” 

8 years into my career, I could apply to any of these positions (purely in terms of career experience). By checking the box of “5 years of experience”, 95% of the more “senior” positions become available. Where you likely have no one to report to that can and will develop you. 

And then what?

You’re just supposed to know everything? 

That’s the situation I’m currently in: 

1. I run my own business. I don’t have a boss or investors that tell me what to do. 
2. A lot of people come to me for career advice (which I’m happy to give). 
3. I now have the job experience that would empower me to take on a lot of different management jobs in the startup world. 

All of that should make me feel like I know everything.

Whereas in reality, I know very little. I’m still figuring out new and old stuff on a daily basis. 

It just doesn’t feel socially acceptable to know very little at this stage. 

Here’s what I’m doing about it: 

1. Adopting a beginner’s mind
2. Surrounding myself with coaches & mentors 
3. Building public and private accountability mechanisms 
4. Read voraciously 
5. Not being afraid to admit I don’t know 

Let’s dive in. 🤿

[1] Adopting a beginner’s mind

In 1942, the married couple Abraham & Edith Luchins ran an experiment (they’re both psychology researchers, they don’t do this for leisure): they gave people three different water jars with different capacities, and asked them to measure out a certain amount of water.

For example: you get 3 jars – A holds 21 units, B holds 127, and C holds 3. The task is to measure out 100 units. The solution would be to fill up jar B, and then pour out A once and C twice. B - A - 2C. 

They then continued to give the subjects puzzles with that exact solution. Until at some point, they presented a puzzle with a simpler solution: A holds 15 units, B holds 39, and C holds 3. The obvious and simple answer would be A + C. Even an elementary school child could figure this out. 

But the subjects who solved the other riddles before still applied B - A - 2C. Which also works, it’s just more complex. But they didn’t see the obvious solution. 

This is the Einstellung Effect: always solving a problem in the same matter even if a better solution exists. (Charlie Munger calls this “man-with-a-hammer-tendency”: to a man with a hammer, everything looks like a nail.) 

This could be part of the reason why it becomes harder to find a new job with 20+ years of experience: because they’ve built a larger toolkit, they view new problems through the lens of that toolkit, even though better solutions might be out there.

(This is a hypothesis, I haven’t done any research into this but would be curious to learn more.) 

A good counter to this is the Japanese concept of shoshin: adopting a “beginner’s mind”. When you first start out doing something, you know nothing. So you try a lot of things and ask a lot of (potentially dumb) questions. The more expert you become, the less you do this. Unless, of course, you never lose your shoshin. 

As a generalist, it’s easy to fall into the trap of thinking you’re an expert at everything. Which you aren’t. You will never outcompete the specialists at their discipline. That’s the point. 

Take recruiting. I run a recruiting business; but I will never outcompete a full-time talent acquisition manager at recruiting itself. I might deploy different techniques from other fields to get better results, but as long as I’m playing their game, I will never be able to “win”. 

That’s great! Specialists are a treasure trove of information – as long as you retain your beginner’s mind, and aren’t afraid to ask dumb questions, challenge your assumptions, and try new things that might seem silly at first. 

So whenever I meet a seasoned recruiter, I try to learn as much as I can from them. Without pretending that I know everything about recruiting – they’ll smell that from a mile away. 

(This, btw, is also how you build a good network: by asking a lot of questions. People love to talk about themselves much more than they enjoy listening to others.) 

[2] Surrounding yourself with coaches & mentors 

In a corporate world, you have a manager, and that manager has a manager. These can serve as mentors to guide you, teach you, and serve as idols. 

As entrepreneur or in an early-stage startup, you likely don’t have this. Your manager might be a guy in his early 20s who’s also just trying to figure out shit. (If you’ve worked for or with me in the 2010s, you know what that feels like.) 

Figuring out everything yourself shouldn’t be a point of pride. 

Understanding that you know very little and roping in others to coach you should be. 

Professional athletes at their absolute peak have plenty of coaches – both LeBron James and Patrick Mahomes have a trusted strength and conditioning coach, as well as several positional coaches for their respective sports (and probably a lot more: mental strength, nutrition, you name it.)

For us generalists – that want to perform at the absolute best level –, this shouldn’t be any different: we need coaches, too. 

I work with: 

• A business & leadership coach 
• A strength & conditioning coach 
• Several Lacrosse coaches in my respective teams 
• A psychotherapist, occasionally 

On a more informal basis, I’ve surrounded myself with people that are a few steps ahead of me: 

• A former Silicon Valley CRO
• A prolific Angel Investor 
• Lots of friends from the startup world that challenge my thinking

And the only thing I can think about is: do I have enough coaching around me? 

Why would I invest a lot of time and effort to make the mistakes everybody needs to make if I could just pay someone to tell me what to avoid? 

You are responsible for your own development. 

Not your manager. Not your partner. Not your parents. 

You. 

So surround yourself with people that develop you. 

You might find this 3-step investing strategy helpful as well: 

[3] Building public & private accountability mechanisms

What gets measured, gets managed. – Peter Drucker

Where attention goes, money flows. – Alex Hormozi

When are you most productive? If you’re like 90% of people, it’s right before a deadline. 

Because a deadline gives you accountability – you have to do something, or there will be consequences. 

How you design these consequences is up to you. Some people prefer the carrot, some the stick. 

For example, you can leverage a “fear of looking stupid” by posting about what you’re going to do next week publicly: 

And holy hell, this worked well (besides a ton of snowfall cancelling practice on Thursday, did shoulder strength work instead). 

“Building in public” helps greatly with accountability. But if you don’t like others to know about your struggles, you can also do this in private by: 

• Implementing quarterly OKRs and weekly KPIs for yourself
• Having a friend as accountability partner with whom you report regularly
• Keeping a index card nearby where you document your activities (see this article, scroll down a bit)

[4] Read voraciously 

A book allows you to consume the condensed learning of >10.000h within ten hours. You won’t get better leverage than that anywhere. 

So read, read, read. You know this. I know this. But without systems, it’s easy to forget about reading (and to forget about what you read). 

What works for me: 

• Reading at breakfast and before going to bed
• Listening to podcasts & audiobooks while in the gym 
• Making the “Reader” app the default app on my phone (here’s how you set up the system)
• Document your learnings using the Index Card Method

I will also buy the occasional online course to dive deeply into a particular topic. (Most recent purchase: Painkiller by Katelyn Bourgoin.) 

[5] Not being afraid of saying “I don’t know” 

Small minds have an opinion on everything. 

Great minds know when not to have an opinion. 

In my 20s, I thought I had to know everything. And when I didn’t, I tried to make up something in order to explain. 

In my 30s, I simply say “I don’t know”. 

With elections coming up in Germany, people will ask all sorts of questions like “what’s your take on issue X?” More often than not, I simply haven’t done enough information gathering to form a proper opinion.

So I usually reply with “I don’t know. Based on first-principle reasoning, here’s why I think the way you framed it makes sense [or doesn’t], but I haven’t formed a proper opinion.” 

This saves you a ton of painful arguments that you’re bound to lose.

But most of all, it’s honest. 

You don’t need to have an opinion on everything. 

In closing: 

• You’re not supposed to know everything. 
• Quite the opposite – it’s healthy to understand that you know very little. 
• Because that allows you to do something about it – like the 5 things above. 

I’ll leave you with a quote from my favorite childhood band, Wise Guys (in German): 

“Ich weiß, was ich weiß, doch nur das, was ich nicht weiß, macht mich heiß, weil ich’s gerne besser wüsste.” 

Happy Monday.

LFG. 🔥

PS: If you’re still not sure who to vote for in the German elections on Sunday, I encourage you to read my friend Niklas’ article on “how to vote consciously”. Deeply researched with a lot of secondary data to dig deeper on.