Too Scared To Try, Too Entitled To Win
There’s a strange dichotomy I notice in coaching clients.
We are far too hesitant when it comes to following our passion. Deep down, we think a creative path is impossible for “ordinary” people.
At the same time, we are far too entitled when it comes to outcomes. We want to be wildly successful — or nothing.
That’s a problem.
The Paradox in Action
Here’s how a typical coaching conversation might go:
Client: “I want to be a writer / content creator / comic book artist [fill in the blank].”
Me: “Great. Let’s set up a plan and daily habits that will get you there.”
Client: “Oh, but I don’t believe it’s realistic. That kind of life is only for a select few.”
Me: “You can absolutely make a living doing this, though probably not six figures right away.”
Client: “Well, then I don’t want that.”
Do you see the issue here?
We dismiss the possibility of being a working writer, yet daydream about topping bestseller lists. We consider an online business too risky, yet expect the first try to be a unicorn.
It’s a double punch to stop any dream dead in its tracks.
Why We Stay Stuck
There are two forces at work here:
Unfamiliarity bias: All around us, we see people who did the usual thing. They went to college, got a job, bought a house, etc. But how many people do you know who made it as an artist or an online entrepreneur? Few, if any. Their absence makes the path look impossible.
Status protection: We feel we must justify stepping off the beaten path with superstar-level success. Being Beyoncé and making millions is acceptable. Being a $45,000-a-year voice coach feels like admitting defeat to ex-colleagues with “proper” corporate jobs.
Together, these beliefs create impossible standards: don’t try at all, unless you can guarantee greatness.
The Hidden Cost of Safety
Faced with these odds, most people choose the conventional path. But this choice comes at a price.
You are committing to a life of silent suffering.
Most professionals won’t admit it, but every Sunday night, they dread Monday morning. Every workday, they watch the clock. Monday through Friday, they fantasize about the weekend — the two precious days when they finally get to make their own choices.
This is what you get when you are both too scared and too entitled — you end up in corporate hell.
A Different Approach
If fear is the first obstacle, then the remedy is exposure. You need to see with your own eyes that creative careers are possible. That means seeking out people who are already doing it.
For example, when I started out as a digital nomad, I strategically sought out people who were already living the location-independent lifestyle I was aspiring to.
Some of them, I met at local meet-ups or online. With others, I went so far as to visit them in different countries. In the process, it became clear as day that it can be done and that I would be able to pull it off, too.
If entitlement is the second obstacle, the antidote is reframing success. What if the goal isn’t to become the next Steve Jobs or Stephen King, but simply to spend your days doing work that excites you?
That shift lowers the stakes. You don’t have to justify your choices with billionaire outcomes or bestseller lists. The win is getting to do the work itself.
For me, the litmus test for success is the 10 minutes after waking up. I spend these still lying in bed, thinking about the day ahead. Most days, I feel downright hungry to work on the projects I chose for myself, like writing this newsletter or talking to a certain coaching client. Unlike many people, I feel energized, not depressed.
Success — real success — is doing the work for the love of the work.
It is the musician picking up their guitar and nailing that solo for the first time. It is the writer reading the new chapter they wrote yesterday and realizing how it pulls the reader in. It’s noticing, mid-coaching call, how your words suddenly connect with the client.
This is possible — for you, too. And it is intrinsically rewarding.
Bonus Tip: Lower the Bar With Location Independence
There’s one more move that makes both obstacles easier: build a passion project that you can execute online.
Why does this help with the “too scared” problem?
Because the numbers change dramatically. If you’re in San Francisco and need $6000–8000 a month just to survive, becoming a comic book artist or online songwriter feels impossible. But if you’re in Thailand or Colombia and can live well on $1000 a month, suddenly that dream looks far more realistic. The bar is much lower. Also, in these places, you will meet plenty of other creatives who already had the same idea. This will help with the unfamiliarity bias.
And why does it help with the “too entitled” problem?
Because maybe you’ll never make millions doing your thing. But you don’t have to. While your former colleagues are stuck in gray cubicles, you’re taking client calls from a beach café. Trust me: Status anxiety hits differently when your backdrop is the ocean. If you ever feel you’re “losing” the corporate game, just send yourself a postcard from paradise.
No beach for me this winter! I am flying to Bansko on October 1st, a small mountain town in Bulgaria that has become a digital nomad hub in recent years. Starting at the end of December, it also becomes a bustling ski resort. So, snowboarding instead of surfing — if my knee holds up. I’ll keep you posted.
Talk soon!
Niels