Problems: Out with the old, in with the new

On finding confidence from past wins.

Problems: Out with the old, in with the new

“I bottled that, didn’t I?”

“Yeah, we’ve spoken about this before, you need to work on your positioning when you speak to the execs”, my manager says as we leave the boardroom.

Oof. Another meeting, another failed attempt at presenting a product update to our directors.

Same feedback every time – you need to position your presentation better. You need to create more context. You can’t just jump right into the profit results, you need to hold them by the hand and take them through your calculations. Every time I would be given the reins to lead the meeting, only to see my manager take over at some point because I lost the room.

I remember making diary entries about this. Entries that I'm sure I could track down, but I’m not eager to open those old wounds again. Things like: ‘I wish I was as good at pitching ideas as my manager. I wish I was as good a storyteller as my dad. I wish I was as eloquent as some of my colleagues.’

At the time, this was my biggest problem.

Fast forward 9 years and I can hardly remember struggling with this issue.

Now presenting feels natural to me.

I find it easier to think on my feet. By working on this skill, I’ve solved the problem away. By doing more public speaking, by teaching others and mentoring others, I’ve become better at reading the room. To the point where I can’t remember ever having had issues making presentations. Maybe I should re-open those diaries after all.

It’s only a problem until it’s gone

That’s the funny thing about self-improvement, right? You forget how far you’ve come because you can’t remember how it feels to have the problem you’ve solved away. How can you feel it if it’s no longer there?

I’ve experienced the same thing with other seemingly big challenges in the past.

When I moved to Germany I couldn't speak a word of German, it felt like a daunting task to learn a new language at 29. Now three years later, I can hold a decent dinner conversation, talk with my German running buddies and even run a presentation auf Deutsch.

Same for writing. If you told me 18 months ago, I’d have close to 50 newsletters by now, I would have laughed. Ditto for illustrating. I never considered myself to be very creative. I hadn’t drawn something since school. I have subsequently taught myself how to create digital art (like the image below) and I’ve taught other people how they can build this skill as well. Not bad!

All of these challenges seemed intractable at the time. All of them were subsequently solved. Walls that once looked unscalable no longer look that tall anymore.

Reframing our problems

Dealing with challenges means moving out of your comfort zone.

This is a good thing. Life is not in stasis. You are living, you are challenging yourself. Wouldn’t it be boring if you woke up every day knowing exactly what was lying ahead? Knowing exactly how to overcome everything that was thrown your way?

I like what Charlotte Grysolle says about the neuroplasticity of our brains:

“You're trying something new & feeling frustrated? GOOD. Embracing that discomfort and digging deeper is exactly what you need for rapid learning.”

When the going gets tough, reframe the discomfort. Look at it as a good thing.

Upgrading our problems

The more problems you solve, the more new challenges get thrown your way. Fun!

As Christin Chong, PhD tells her coaching clients:

"I'll trade your current problems for new problems"

My biggest challenge at the moment is doing cold outreach and marketing my actuarial services. I don’t love it. I find selling & marketing myself gross. But I also know it’s an important skill I need to develop if I’m going to help build a successful consulting business.

To make things worse, today I found out I hadn’t won a consulting gig I’d been hoping to sign with an insurance company. This came after six months of back-and-forth trying to secure their business.

It sucked. You can ask my girlfriend - I wasn’t a joy to be around today. I’m still licking my wounds.

It’s a case of back to the drawing board.

Zooming out a little has given me some perspective. While the current problem looks insurmountable, this is just the latest one in a list of (previously solved) problems.

Looking back at the tall walls I’ve climbed before gives me the confidence that I can climb the next one.

If you’re facing a big challenge today, think back to your past wins. Your problems are not intractable. You can overcome them.

Thanks to Alissa Mears, Emma Dorge, Frank Corrigan, Karena de Souza, Amer Ameen and Nic Rosslee for reading drafts of this essay and providing excellent feedback. This essay was written during a Writing Sprint — a 7-hour writing challenge with 45 writing peers to go from idea to draft to published in one day.

Originally published at on June 23, 2023.