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Hey! 

If you’re reading this and wondering why you were sent this email, let me give you a quick reminder…

My name is Benji. 

I recently ran the length of Great Britain, but prior to that I’ve spent the last few years building this newsletter around ideas of self-development, wellbeing, and human flourishing. 

It’s a bit awkward, because for someone who makes a lot of noise about how much of life comes down to consistency and discipline, I’ve been pretty poor at keeping on top of this email newsletter. 

You likely signed up at some point along the way because you either saw an ad for this newsletter, know me personally, or simply came across my content online and signed up to read more. 

I’m dedicating right here and now to resuming sending weekly newsletters. Hopefully for many years to come. But at the very least for a good while. 

With that re-introduction out of the way, let me try to deliver you some value in this email... 

The 5 ideas that changed my life this month 

I’ve spent the last 30 days posting short 60 second videos to my Instagram to try to A) improve my public speaking skills, B) overcome my fear of being judged, and C) help sort through and clarify some of the lessons I’ve learned this year. My rules are simple: one take only, and I have to post whatever I record. 

I’ve posted 30 videos exploring different ideas, and I thought I’d share the 5 that have resonated the most with people. 

Here are the five most impactful ideas so far…

1. Do it or don’t - you will regret both

“Do it or don’t, you will regret both.

This is a line from Søren Kierkegaard’s book, Either/Or.

It sounds quite depressing—until you realize that the point being made is not that in life we should try and avoid regret. But rather, if we are aware that whatever path we go down, we will end up with regret, all that is left to us is to decide which set of regrets we would rather have.

If you start a business, the business might fail and you will regret the lost time and the lost money. If you don’t start the business, then you may regret not knowing what could have been.

And it’s just on you to ask yourself: which regret would you rather have?

For me this year, I ran the length of the country and I knew that I was going to have to give up a lot of social events, time with friends, things that were important to me relationship-wise.

And honestly, I do regret that.

There are certain friendships that I regret not being more present for this year.

But if I hadn’t done the run, I would have regretted that so much more.

And so it’s simply about knowing you cannot avoid regret.

You simply have to choose which regrets you would rather live with, and then be okay with making that trade-off.”

2. One year of obsession can change your life

“A one-year obsession can change your life.

May 2025, I ran two miles in just under 20 minutes.

May 2026, I drove to the top of Scotland and then ran a marathon every day until I hit the bottom of England.

I raised this comparison because I want to point out that I don’t think I had anything that special going for me physically.

What I think I did have was a willingness to be obsessed and to get obsessed over something and to work really intensely for a season until I achieved that thing.

It reminds me of something I heard from author and investor Naval Ravikant.

He said that it’s better to work like a lion than a cow.

A cow grazes all day.

They’re just munching and munching and slowly getting stuff done.

A lion lies in wait, rests, and then when they see the opportunity, go after it with ferocity and intensity.”

3. The cost of giving your all

“The cost of giving your all is that you have nothing left.

I just finished, two months ago, running the length of a country.

And honestly, if you told me beforehand that one of the hardest things would be what came after finishing, I probably wouldn’t have believed you.

We all know that there’s a cost and there’s a price to be paid when you do something.

And for me, I knew that I would have to train hard, and there was a lot of sweating and crying and all the effort that went into getting in the shape and the preparation to be able to do the thing.

But what I wasn’t really anticipating was that after I was finished, it would take me months to recover emotionally, physically, mentally.

I would be having recurring dreams about still running. Emotionally, I’d be having, like, nervous breakdowns over the most silly things.

I would be unable to run, unable to lift weights. You know, I’d be needing a spotter on weights that I used to warm up on.

I would be indecisive, have, you know, trouble making decisions, brain fog all the time, just extreme fatigue.

I kind of just thought I’d finish and that I would feel amazing.

And I did feel amazing, but you just can’t get around the fact that I kind of just destroyed my body for a couple months, and there was a price to be paid after that as well. You know, just the caffeine withdrawal alone was pretty crazy.

So, yeah, I think—I don’t know that there’s a lesson here really.

That’s just something I learned, is that for anything worth achieving in life, you’ve got to be willing to pay the cost beforehand, but you also have to be willing to pay the cost after.

And obviously, I’m talking about running. This can be anything.

Posting content like right now. You know, there’s a cost and there’s effort that goes into building an audience, but then once you’ve done it, the harder cost sometimes is afterwards.

Okay, now maybe you have less privacy. Now you’ve got an expectation to serve that audience.

There’s all these costs that come before and after, and you have to be willing and ready to pay both.”

4. Keep your promises

This was a strange one. 

I accidentally messed up while recording this post and ended up just sitting in silence for 60 seconds.

But I decided to post it anyway and explain that it was more important to me to keep my promise of only giving myself one take rather than redo it.

This idea resonated with people, and the lesson for me was simple: people value authenticity and integrity more than they value a polished script or perfect video. People respect people who keep promises.

5. If the worst case is nothing happens, you should just do the thing 

“If the worst case is nothing happens, you should just do the thing 

If you’re not familiar with the concept of asymmetric bets, this honestly might be one of the most useful videos you see today.

An asymmetric bet is simply a bet where the downside, the potential downside if the bet does not pay off, is either limited or practically non-existent. But the upside if it does pay off is enormous or potentially unlimited.

So I’ll give you a few concrete examples.

If I take £1,000 and start a business, my downside, I know my downside. If the business doesn’t work out, it’s that £1,000. But if the business does work out, it could be far more. You know, it could be 10, 100, a million. It could be so much bigger than that initial £1,000.

So the upside is disproportionately large compared to the downside.

What about applying for a job?

If you apply for a job, the potential downside is that you get rejected or simply you don’t even get called. That’s a limited, small downside. The potential upside is your future career.

Let’s talk about some examples that are a little less obvious…

If you go to a store, get to the checkout and you ask them, “Hey, do you happen to have a discount on this item?”

It’s uncomfortable, but that’s the only downside. A little bit of feeling uncomfortable. The potential upside is a fair bit of money saved, which I think most people would say disproportionately outweighs the downside.

This, what I’m doing right now, posting on social media — the downside is sometimes nobody cares and the video flops, but that is a limited downside. The potential upside is huge. Your video could reach tons of people, and you don’t know who any one of those people could be.

The moral of the story is just to be on the lookout in life wherever you can for asymmetric bets.

And if you keep stacking enough bets where you have little to lose and lots to gain, eventually you will win.”

There you are—five ideas myself and a few others have found impactful this month. 

I’ll send a similar round-up at the end of next month, but in the meantime I look forward to updating you on what else I’m reading, learning and training for. 

(If you want to see all the updates, not just the top 5, you can follow my Instagram here.)

See you next time. 

Thanks for reading!

Benji

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