The Dangers of Delegating


Hey friends,

I’ve been planning my trip to Istanbul this week – researching restaurants, places to visit, fun activities. I was thinking the whole time: “hey, I could just get my exec assistant Dan to do all of this and give me an Istanbul itinerary”. But I decided to do it myself.

Now, that’s a bit out of character for me. I always preach that delegating and outsourcing frees up your time for higher ROI activities. Like in 10 Time Management Tips That I Genuinely Use Everyday, where I talk about calculating the dollar value of your time:

But what I realised planning this Istanbul trip is that doing the leg-work yourself unlocks a bunch of hard-to-quantify side-benefits:

  1. Planning the holiday is part of the fun – it builds up anticipation.
  2. I value experiences more if I understand exactly why I’m doing them, and what the alternatives were.
  3. Researching gives me more context, which makes me enjoy the trip more than if I just wandered around Istanbul knowing nothing about the city.

Mr Money Mustache makes a similar point about cycling instead of driving to save money. Sure, you save on fuel costs if you cycle to work. But you also unlock a bunch of sneaky secondary benefits by doing things yourself:

🚴‍♂️ Cycling vs Driving → Fitness, better posture, fresh air and sunlight

🍕Homemade Pizza vs Takeaway → Healthier, a fun family ritual, you perfect a skill.

🔨 DIY vs Builders → Learning a new skill, a more personal connection to the outcome, not staring at a screen.

Then there’s just the satisfaction of doing it yourself. A lot of the best times I’ve had are when I cooked a big meal with friends instead of ordering Deliveroo, or spent a whole day building IKEA furniture with flatmates. Sometimes both of those things at the same time.

So in the future, before delegating a task I’ll try to think: what non-obvious benefits might I miss out on? Would this be a joyless waste of my time, or a good life experience?

Have a great week!

Ali xx

PS: Laundry and cleaning are still very much on my “outsourcing this is awesome” list. Would recommend, if you’ve got the disposable income + you don’t inherently enjoy those things.

PPS: Fitness journey update: it’s going well. I’ve been going to the gym x2 or x3 times a week. Even on days when I don’t feel like going, when I actually do, I end up feeling way more energised for the rest of the day.

🤝 Get help finding a fulfilling career that does good, too

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♥️ My Favourite Things

📚 Shortform Summary – Originals by Adam Grant. Originals makes loads of great points about originality and creativity, but tbh it’s a bit too long at 200ish pages. Enter the Shortform summary, which boils everything down to just 10 pages (one for each chapter), and includes some short exercises to test whether you absorbed the content.

📝 Article – How Will You Measure Your Life? by Clayton Christensen. Great article that talks about not defaulting to work during your spare hours. Unlike most of his friends, Clayton tried to dedicate his occasional spare hours to “figuring out his purpose in life”, instead of pouring even more time into his work. And he feels that’s paid long-term dividends, when he looks at how many other graduates from Harvard Business School end up with difficult marriages, mental health problems, or struggling to function outside their work.

🗒️ Tech – Moleskine Smart Notebook. Probably the most ridiculous thing I’ve bought this year. It’s basically a £160 (now £108…) pen from Moleskine with a camera in it that reads what you’re writing in your paper notebook, converts it digitally, and transfers it to your iPad, phone or computer. In real time. Sadly the battery doesn’t last that long and it has a few weird quirks.

🧙🏻‍♂️ Movie  Fantastic Beasts: The Secrets of Dumbledore. I saw this last weekend. Wholesome, heartwarming stuff. The plot was a bit all over the place, but hey, I’m only really there for the Harry Potter nostalgia.

👕 Clothes – Chinos from SPOKE. I’ve bought about five pairs of these chinos. They have lots of different fits, nice comfy material, and look pretty good.

✍️ Quote of the Week

Young people in Europe and North America in particular, but increasingly throughout the world, are being psychologically prepared for useless jobs, trained in how to pretend to work, and then by various means shepherded into jobs that almost nobody really believes serve any meaningful purpose.

From Bullshit Jobs by David Graeber. Resurfaced using Readwise.

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