11 Practical Pieces of Advice I'd Give My Younger Self

"The quality of your work will eventually catch up to your ambition."

These days, people love to make small talk starting with the following: “Man, 2020 has been a really shitty year.” 

While I understand the sentiment, I can’t bring myself to nod in full agreement. This year has been absolutely devastating for a myriad of reasons, but it has also had a few bright spots. I got married, left my job, started a business, and moved to a new apartment. 

When I was younger, I would let one awful event ruin my day, week, or even month. Every time something good happened, the awful thing I worried about would loom over me like a perpetual dark cloud. One of the biggest lessons I’ve learned this year is that good and bad can co-exist. When something’s bad, it’s not all bad, and vice versa.

My birthday is approaching, so I wanted to reflect on my 28th year of life and share some practical nuggets that I’ve found useful.

1. The quality of your work will eventually catch up to your ambition.

I’ve been working on The Profile for three years. It’s come a long way since then. The reason it has gotten better is because I didn’t give up on it — even when it was bad.

Ira Glass says that everybody who does interesting, creative work went through years where they had really good taste and could tell their product wasn’t as good as they wanted it to be. It fell short. And that’s exactly when most people quit.

It took Glass 10 years of podcasts for him to feel like his taste caught up to his ambition. The only way to close the gap between taste and skill? Doing the work week after week, day after day. “It is only by going through a volume of work that you're going to catch up and close that gap,” he says.

2. Find ways to fall into intellectual rabbit holes.

When I sit down to write, I typically draw on my experiences for ideas. But during quarantine, those real-life experiences have dwindled. So I’ve had to learn how to create an environment that facilitates falling into rabbit holes.

The first way I do that is by pestering interesting people to have conversations with me. The second is to go on a walk outside and actively observe my surroundings. And finally, I sometimes just take a book from my bookshelf, open it to a random page and start reading. Ideas are all around us … we just need to notice them.

3. Take mental breaks throughout the day.

After a long period of staring at the screen, my mind starts screaming. That’s when I know I need to take a break. For me, there are several activities that soothe me, and I use them to break up my day in three chunks.

In the morning, I do 10 to 20 minutes of yoga. In the afternoon, I exercise for about 30 minutes. And in the evening, I take a walk with Anthony for about 45 minutes to an hour. All three things are physical because they get my blood flowing, allowing me to step away from technology and let my mind wander. This has been the single-best, most-rewarding change I’ve made in the last year.

4. Chase what you don’t know.

It’s so damn easy to label ourselves a certain type of person. For a long time, I was a “journalist.” Suddenly, I’m an entrepreneur! Who knows what I’ll be five years from now? The point is not to let your identity become stagnant.

Actor Willem Dafoe, who has played a Spider-Man villain, Vincent van Gogh and Jesus, says that so much of what we do is predicated on an idea of ourselves that we’re trying to protect. It’s part of the reason he enjoys playing such a range of characters. He’s always chasing after what he doesn’t know. “Do things that don’t let you decide definitively who you are and the way things are,” he says.

5. Be interesting, not perfect.

I used to optimize for perfection. Now I optimize for being interesting. Think about the favorite people in your life. Do you care that their hair is perfectly combed? Or do you not even notice that because you’re so captivated by their brain?

Whether it’s art, movies, or books, people talk more about the flawed things that get stuck in their heads than they do the obvious, perfect things. Malcolm Gladwell says, “You want an aftertaste, and that comes from not everything being perfectly blended together. The question is: What is interesting? That’s what has to drive any creative act.”

6. Competence is the antidote to fear.

I used to be absolutely terrified of public speaking. At the thought of it, I’d start nervously sweating. But here’s the thing: Things aren’t scary. People get scared.

I learned this from astronaut Chris Hadfield. He uses the following example: When you first learned how to ride a bike, you were fearful because you could crash and hurt yourself. Then, as you got better and more confident in your skills, it became silly to be afraid of a bike. Yet the bike itself didn’t change — it remained just as dangerous as it always was. You are the one who changed. Competence breeds confidence.

7. Your choices belong only to you and no one else.

One of my biggest worries before I left my job at Fortune was: “What if I disappoint someone?” When I think about this question now, I am amazed at the self-centered assumption it implies. Who — aside from my incredibly supportive family — cares so much about my life choices that they would be …. disappointed?

The brutal truth is that we’re all busy navigating our own lives to have enough time to be disappointed in other people’s decisions. I’ve learned to normalize my life. Do whatever makes you happy, and stop letting other people’s misinformed judgements dictate your day-to-day. 

8. Love is not an emotion; it’s a skill.

Everything in life — yes, even love — is a skill. When I asked couples for their best marriage advice, the one thing that kept coming up is that they understood that a loving partnership is a constant work in progress, and there’s always room for improvement.

One reader told me, “It has to be worked on; sharpened regularly. Much like any other craft, the time that goes into keeping it fresh and vibrant must be respected. And like all important skills, it must be used.”

9. Life is about good people and good stories.

Because we’ve all been in quarantine for months now, I’ve become much more intentional about the people I want to spend time with. Although my circle of friends has gotten even smaller, it’s grown exponentially in terms of amazing conversations and unforgettable memories.

As Shonda Rhimes put it: “I now work to see people, not as I’d rewrite them, but as they have written themselves. I see them for who they are. And for who I am with them.”

10. No matter what, always bet on yourself.

One of the more mind-blowing things I’ve realized in the last year is that no job, no person, no amount of money will ever fulfill me if my self-worth is tied to something external.

I’ve written about this before, but it’s incredibly liberating to have your identity tied to your own name. The best thing I did is start The Profile in 2017 because it gave me another identity — one that allowed me to be 100% myself.

11. Get proximate to suffering.

After everything that’s happened in 2020, it’s become crystal clear that many of us live in a bubble. To better understand other perspectives, we’ve got to get curious and break out of our own narrow views of the world. Visit a shelter, volunteer at a food bank, or help someone going through a tough time.

Here’s what Bryan Stevenson taught me: “We must get proximate to suffering and understand the nuanced experiences of those who suffer from and experience inequality. If you are willing to get closer to people who are suffering, you will find the power to change the world.”


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