Advice I keep emailing myself

I don’t know about you, but I send myself almost 100 emails a day with things to do and thoughts I want to remember. Because as I go through my day, from to do to to do, meeting to meeting, walk to walk, Uber to Uber, I think of the current state of my life, the things I’m doing well and wrong, the things I wish I could make happen, the people I wish I spent more time with. And for someone who’s obsessive about getting to inbox zero this is the best system I could come up with to force myself to go through these observations again before copying them to some document and probably forgetting about them.

I’ve noticed trends in thoughts that keep re-emerging. Here are some of the more popular ones, in list format just as the Internet likes it.

1. Spend (a lot of) time with people you like.

Sounds crazy obvious but I have a hard time staying true to this and don’t think I’m the only one. It’s so easy to get sucked up into some form of social commitment just because someone suggests it. It just pops up in your inbox or in your text messages or among your roommates. You don’t really want to do it but it doesn’t sound that bad and you don’t want to offend anyone and say no to some activity.

But it does pile up and starts significantly eating away at your time.

I’ve been somewhat of a yes man for the past year but do like this wise adage which I am now paraphrasing:

“When you say yes to something, remember that you’re actually saying no to everything else…”

Try only saying yes to the things that you really, really want to do.

Needless to say this applies to the people you work with, which usually represents the largest chunk of your life.

Do not be complacent about the people you work with. You’re allowed to be picky. If you’re not feeling it, run! Your time is so so short.

When you find people you really like or love, people who make you feel like you want to and can do everything, people who you understand and who understand you, people who you are not only seeing for a very direct, short-term reason, spend a lot of time with them. Give them the lion’s share of your day and life. They deserve it and so do you.

2. A similar, yet more general insight: be proactive instead of reactive.

My friend Emil called me up the other day with a similar realization.

Remember: you don’t have to give priority to the emails that arrive in your inbox. You are the only one responsible for achieving your goals and those emails just represent what other people want of you.

It’s natural that you should answer them at some point but make sure you’re aware of what your priorities are and deal with those first.

You could spend your entire days simply reacting to every push notification that gets sent your way and do nothing else.

So, what do you actually want to do today? Who would you like to see? What would you like to change about your current situation?

Think about it.

3. Do the hard work. The stuff that feels messy, and uncomfortable, and scary, and new, and like a struggle.

You think anyone likes filling those government forms, following up with a customer about a payment they have to make or asking for legal advice? No, but if you start making a point of doing the hard stuff, the boring, painful, administrative drudgery that stands between you and everything you’ve every wanted, you’ll get better at it.

It’s just like going to the gym, it’s just like drinking black coffee without sugar or whiskey on the rocks with nothing else, it’s just like any other good old tough habit that’s an acquired taste. We get used to things. Get used to what is hard and you’ll feel better. You’ll feel like a real person who can get things done.

File those taxes, get that visa, renew that driver’s license, talk to those damn customers, have that difficult discussion with your co-founders or spouse or kids. Whatever it is. There’s always an elephant in the room. So quit beating around the bush and get to it.

I fundamentally believe that we know what we need to do to get to where we want. The real question is whether we’ll do it.

Something that has helped me start tackling more of these painful things sooner is the hard-earned awareness that it’s going to be tough and messy anyway. It’s not like it doesn’t have to get done at some point. So why not just do it now?

4. Notice what it is that makes you feel energized and happy and do more of that.

An interesting point to follow the last one. Although I am convinced that you must get used to doing the hard stuff, I also believe that you should pay attention to what feels easy, natural, fun, invigorating, exciting, incredible and do more of it.

I heard that at the famous Bollettieri tennis academy, they take a slightly different approach. Your traditional coach, upon noticing that your forehand is clearly stronger than your backhand, would have you work day in and day out on improving your backhand and bringing it up to speed.

Bollettieri on the other hand would have you further develop the imbalance between the two. If your forehand is good and your backhand is only ok, they would have you turn your forehand into a real weapon at the expense of your backhand. Reminds me of the insight that the great companies have both very obvious strength and weaknesses.

I think balance is boring. I don’t know why people think normal and well-rounded is a good thing. It just means you’re replaceable because you never took the risk to express yourself as you are but simply conformed to an archetype that was expected of you.

It was easier to fit into a type than to be an individual.

Obsession is what makes life worth living.

If there’s something that you love, let it consume you.

Or as Bukowski would say…

5. Become who you want to be today. Not tomorrow.

I want to become a public speaker. I want to smile more and make more eye contact. I want to talk to the strangers I want to talk to in the street. I want to wake up early. I want to have a girlfriend who I really care about. I want to do more focused work and generally be better off at sectioning off my day into heads down and heads up moments. I want to feel fewer petty emotions — the little every day upsetednesses, the little jealousies, insecurities, impatiences, let them dissolve and make room for what is really important. I want to feel more empathy, be less anxious, be more grateful, be more focused, meditate, run, travel to countries I wouldn’t normally go to…

Yes, it can be absolutely terrifying to think of all the possibilities and permutations the world has to offer. What are you supposed to do when there are a thousand branches to choose from?

I face this option paralysis all the time.

The good news is, if you think about it, there really is only one thing that matters at any point in time. One thing you have to do, focus on or fix.

All the rest is just pretty important. Not crucial.

I’ve found that viewing the world in this way has helped me narrow my focus and forced me to prioritize.

This is very difficult, especially for someone who wants to be everywhere and do everything like me, but it’s possible.

6. Be honest about how you’re feeling and what’s wrong.

If I think about it, my life can be broken down into periods or movements, and during each one of those I had a dominant mindset and outlook on the world.

Often, by the way, those movements can be summarized by the books and songs that mattered most to me at the time.

For example, my sophomore year had an overarching existentialist Kurt Vonnegut / Tolstoy-y mood that was very different from my first post graduation year which had more of a drive-along-the-water-at-night-in-California song feel to it.

In each case, some things went really well and others bothered me a lot. Sometimes it took me months to realize what was wrong. Well… no, I knew what was wrong but I didn’t pay attention to it. That cloud that is hanging over your head… It’ so easy to ignore it and to focus on the immediate, more pragmatic day to day stuff that has to be done. But that doesn’t change the fact that there’s this massive tropical storm of a realization that hangs right over your head and that won’t go away. Just like the hard stuff that I talked about earlier, this is the hard realization stuff that’ll hit you no matter what.

Wrong city, wrong job, wrong group of friends, wrong daily routine, wrong destructive habits, wrong something. Whatever it is.

That’s what has the most important influence on your life so you just can’t ignore it. The sooner you listen to that little voice, the better off you’ll be.

7. Express yourself more, keep producing.

I would really like to write every day. I don’t because when I start to write it’s mostly bad, I feel like what I’m pumping out is low quality, poorly expressed and unexotic, also because other things arise — life mostly — and I do that instead. Email, events, other tasks. I do that. I tell myself I’ll write before I sleep but I get tired.

Sometimes I also get the feeling that I have nothing to say.

I also don’t really like advice blogs and all that. I feel like most of these people become “successful” by telling other people who to become successful…

I hate that I’m writing a 7-bullet point post on Medium.

I prefer novels, stories. I would like to write those. But I don’t have the time, or I keep falling short of the quality that I would like to produce.

But you know what…

I find that it’s better for you to just express yourself imperfectly, for you to fall short of the beautiful work of art that you wanted to put out into the world, for you to cringe at the edits that could and should have been than to not say anything at all.

It will never be ready. I would rather exist and create in an imperfect, human way, than die without having put anything out there.

It’s imperfect? Who cares. Let the critics create instead of criticize.

I could spend weeks rewriting this post. Why the hell are there 7 bullets and not 8 or 9 and while you’re at it why are there any bullets at all?

Maybe I should split each bullet into its own blog post. Maybe I should wait, write more and make this a book.

I’m writing this on a plane to SF as we speak. Well, as I write.

I’ve got other stuff to do. I’ve already spent enough time writing this today. If I start editing this I’ll never get to the other stuff I want to do and I’ll never push anything out.

So yes, make imperfect things.

Love them, and move on.