“Angela, why are all these questions so difficult? If I knew the answers, I’d probably be doing all that already and living my best life!”
A client gasped, when I gave her a set of career reflection questions for the week.
“Well, someone smart once said: adulthood is about wrestling with the difficult questions. By your thirties, all the easy ones you've already answered.”
Growth always hides in the questions we don’t yet know how to answer. If we already had the solution, it wouldn’t be a challenge at all. There would be no growth.
Good questions are good coach' superpower. They crack doors open when everything feels locked. They help us see beyond the false walls we’ve built in our own heads.
Today I want to share with you 3 of my favorite ones, that I use myself and with clients when we are not sure where to go, what direction to take, or what choice to make:
1. What if the worst thing happens?
That exciting and terrifying option you’re considering - career move, relationship, big business leap. What if it fails? Most of the time, the “worst” isn’t as catastrophic as we imagine. We’d survive. Often, we’d return to our normal baseline in a matter of days and weeks. And if you don’t have a safety net yet, could you build one so trying feels less like cliff-jumping into the fog and more like leaping into a bouncing mat?
2. Why did I fail?
Trying new things means failing more often than not - failure here is defined as a mismatch between what you expect and how the real world is. But the important part isn’t rushing to the next attempt, bouncing back faster - it’s pausing to ask why. What expectation didn’t match reality? What can I learn about myself, my circumstances, the world? That’s how failure turns into an asset - better mental and world models, sharper instincts, higher self-awareness you can use for your journey ahead.
3. What’s the third option?
Our brains love making fake tunnels: either stay in my corporate job (soul-crushing) or leap into entrepreneurship (terrifying free-fall). But life is rarely that binary. It’s more like an open sky with millions of possible paths. When clients get stuck, I ask: “Pretend neither option is available. What else could you do?” Suddenly, there’s not just a door but a whole field of untaken paths forward. You scale down one thing or take an extended vacation to give other things a try, you can work part-time now while having another side gig, you can try different things in the same company... once we open the "third door", you'll see there are many more you were blind to.
Bonus (thanks, Tim Ferriss): How can I set this up so even if I fail, I succeed?
Like when I started my podcast 6 years ago. Even if it flopped, I’d still make friends with brilliant people, learn a ton, and practice speaking on the fly. Not bad for a “failure.”
So over to you, dear reader: which of these questions resonates with you the most? Try it in your next journal session. And remember - life’s easy questions are already answered. The good ones are waiting for you now.
