Advice to My 20 Year Old Self

I’ve been listening to Tim Ferriss’ podcasts lately and am really enjoying them. Highly recommended. He ends many of his interviews by asking his guests a list of short answer questions, one of which is some variation of “what advice would you give to your 10 years younger self.”

Most people give one or two answers, but others expand and give in depth answers. As I was wandering around Buenos Aires last week listening to Ferriss’ interview with Naval Ravikant, I started to think about what I would tell my 20 year old self. I stopped for some ice cream and started to write my list. After thinking some more, I came up with 20 things I’d tell my 20 year old self. I think there’s four really important things, then 16 more. Here’s what I’d tell my 20 year old self.

1. Never say you know something when you really don’t.

If you say you know something you don’t, there’s only two possibilities:

  1. You end up looking like an idiot because the person now expects you to be able to talk intelligently about the subject
  2. You missed an opportunity to learn something you didn’t know.

I used to do this in high school and college. But as I got older, I realized it was really dumb. One of Entrustet‘s mentors used to test prospective employees and business relationships by saying something like “have you heard how well xyz company is doing?”

Xyx company didn’t exist. And if the person said “oh yea, they’re doing amazing!” he immediately knew that the person was bullshitting. Don’t do it.

Most of the very successful people I know immediately ask for an explanation when they don’t know something. I think it’s one of the biggest reason’s they’re successful.

2. Don’t be afraid to look dumb. You’ll learn stuff faster.

The only way to learn something new is to get your hands dirty and make mistakes. As a 20 year old, I remember not liking to look dumb in front of people, which caused me to learn things less quickly than I do now. I had to get over my embarrassment of looking dumb by force: when you learn a new language, you’re going to look dumb and say the wrong thing all the time.

In my first six months in Chile, I didn’t learn much spanish because I didn’t want to risk saying the wrong thing. But after working at Welcu for about a week (and getting bullied whenever I said something wrong!) I got over it quickly.

3. Develop an exercise routine. It’s really hard to get back into it when you stop, even for a few weeks.

I remember being a 20 year old, playing soccer, basketball and racquetball a few times a week, reffing soccer, biking hundreds of miles a month. I never thought I’d stop. And as soon as you stop, it’s hard to get back into it.

4. Read and write like you’re doing now. Don’t stop. It’s like exercise, hard to start, but easy once you’re in the habit.

At 20, I read at least a book a week. I now read in spurts, nothing for a month or two, then three in a week. I used to write almost daily, now in spurts. Reading and writing are key to staying mentally active. Do it, don’t stop.

Here’s the rest of my list, in no particular order:

Don’t share anything publicly that’s not providing value for other people. It’s going to be tempting to show off or be mean online. Don’t do it. Value your privacy. Low profile is the way to be.

Don’t be lazy with close friends. You have them across the hall and down the street in college, but as they graduate, you’ll drift apart if you don’t make an effort. You can’t expect them to make the effort. It has to be mutual.

Don’t do business with unethical people. It’s just not worth it. Short term it might seem to be good, but long term, it’s not.

Don’t use an alarm clock to wake up unless you absolutely have to. Humans weren’t meant to get up to a horrid noise.

Trust your instincts, they’re probably right. If something feels wrong, it probably is.

When someone’s doing something poorly or screwing up, give them honest feedback as soon as possible. You’d want them to tell you if you were screwing up, so it’s mean, almost unethical not to tell them. You’re not giving them a fair chance to improve. Most people who you want to be friends with or do business with will appreciate it.

Via negativa is the way to go. If you’re unhappy, cut stuff out until you’re happy again, don’t add stuff in. If you’re stuck in business, make it simpler until it works.

Don’t be scared of brutal feedback. Seek it out.

Study or live abroad as soon as possible. Chile made me a different person for the better by forcing me to see things from other people’s perspectives.

Being a big fish in a small pond feels good, but not challenging yourself enough won’t make you happy. Take chances to test yourself against the best.

Don’t be lazy and stop cooking as you get busier. It’s healthier, its cheaper and you like it.

Look for even more Talebean low risk, high reward opportunities.

You were right about valuing experiences over things. Keep it up.

Take present value cash unless you have a Talebean logarithmic upside possibility. If the upside is linear, take the cash.

Tell people exactly what you want as clearly as possible.


  • Posted from my email.

    My aunt:

    I forwarded your blog to XXXX and asked what he would tell his two-year-old self. (He is 12.) Thus is his response:

    12 year old:

    Don’t cry.

  • Great advice, especially the bit where you encourage us to read and write regularly. I met an energetic 94-year-old woman in Ireland that credits her daily reading and writing activities to her well-being and mental health!

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