How I’d Have Done My 20s Differently

You won’t take this advice, but I’ll say it anyway

Jon Tyler
Jon Tyler
Feb 16 · 5 min read
Credit to James Wheeler on Pexels

‘What day is it?’ asked Pooh.

‘It’s today,’ squeaked Piglet.

‘My favorite day,’ said Pooh.

First thing each morning, I would get up and eat. Not to enjoy the food, but to fuel my body. Then I’d work all day as a teacher. Then I’d come home and work all evening. And at some point I’d fit in an intense workout too, under the illusion that this was ‘healthy’.

I would shower and do a few other things too, just in case you’re wondering. But never for long. There just wasn’t time. It was all about doing my job as well as possible and climbing that career ladder. To the kind of leadership position I’m in now.

And now that I’m here?

It’s ok. I’m certainly grateful for what I have.

But I can’t help but look back on what I missed out on in my 20s. And how I could have made more of that time in my life. In the same way that when I was in my 20s, I looked back on my younger years and wondered whether I could have made more of them. And even though I’ve got better at living in the moment, the same will probably be true when I hit my 40s.

There’s a line in ‘The Sunscreen Song’ that always reminds me of this:

‘In 20 years you’ll look back at photos of yourself and recall in a way you can’t grasp now how much possibility lay before you and how fabulous you really looked.’

It’s easy for us to look at ourselves and think about what we lack. But I like the way this lyric reverses things, and points out how much we have to be grateful for. If only we’d realize it at the time.

So in short, I suppose I wish I’d have slowed down a little in my 20s and appreciated the journey more instead of always sprinting to the destination. I know, cliche alert. Sorry.

Your own experience of your 20s may be, or have been, very different. Some will no doubt wish that they’d worked harder. Even those who can relate to my story will find advice to slow down hard to take. I know I did. I was too concerned with making it. Whatever ‘it’ is. Money? Status? Career advancement? It’s hard enough not to be consumed by these things now.

But in your 20s, it’s only natural to be too worried about which path to take to stop and admire the scenery.

I can’t change that. I can only channel the spirit of a lawyer and call several witnesses to the stand, who may have been able to help me in my 20s if I’d actually listened to them.

1) Derek Sivers: ‘Writer, entrepreneur and avid student of life’, best known for founding the highly successful ‘CD Baby’ music company.

Derek Sivers is full of wisdom and well worth looking into if you haven’t come across him. His rule for making big decisions is one I still use all the time:

‘If it’s not a hell yes, then it’s a no’.

But for our purposes here, it’s something else he’s said that’s pivotal. He has described how he used to take a regular bike ride that he noticed would always last 43 minutes. And they were 43 minutes that he hated. He’d push, sweat, get red in the face, and end up dreading these 43 minutes of torture.

One day, he just decided to do the same bike ride but take it easy. Go at a nice leisurely pace and not worry how long it took him. And it transformed his experience of that bike ride. He actually enjoyed it and wanted to do it again.

The most striking part though was when he looked at his watch after the ride. 45 minutes. He couldn’t believe it. All that torturous effort before, for only 2 minutes of difference. Sometimes it’s ok to give yourself permission not to go full throttle the whole time. You might even end up better for it.

2) The Dalai Lama, when asked what surprised him the most about humanity:

‘Man. Because he sacrifices his health in order to make money. Then he sacrifices money to recuperate his health. And then he is so anxious about the future that he does not enjoy the present; the result being that he does not live in the present or the future; he lives as if he is never going to die, and then dies having never really lived.’

You may have come across this quote before, but it’s the type that is worth repeating.

It rings particularly true with me because I did sacrifice my health in my 20s. Not consciously. I always ate healthily, worked out religiously, and slept well. But the stress of working so many hours at such a high pace still ended up taking a toll.

Nowadays, I think anyone that knows me would be amazed to hear me talk in any way about slowing down. I’m sure they’d call me a hypocrite. But slowing down does not mean doing less. And these final witnesses prove it…

3) Brad Stulberg & Steve Magness, authors of ‘Peak Performance’.

If you read my most recent article, you’ll know that ‘Peak Performance’ is a brilliant book that might just redefine how you look at productivity.

What it shows above all is the proven importance of rest in enabling you to perform at your peak. As they put it, ‘Stress + Rest = Growth’.

Again, slowing down does not mean doing less. It means taking sufficient breaks and mitigating the ‘stress’ part of the equation enough to be your best self. You can rest more and get more done.


So there you have it. Philosophy from Winnie the Pooh to the Dalai Lama. I wish that I’d been able to take it on board in my 20s. I still need to now.

The truth is that while I’ve got better at incorporating their wisdom into my life, I’m still nowhere near as good at it as I’d like to be. The advice is timeless. But that doesn’t mean you should take your time in implementing it.

So go hard, but take breaks. Load up that ‘to do’ list, but make sure it includes items that you want to do. Feel free to focus your life on working (if you wish), but don’t lose your focus on living.

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Jon Tyler

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Jon Tyler

Responsible for teaching & learning at a top UK school. Trying to get better at life. I write about how maybe you can too.

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