21 Things I Learned in 2021

Our lives are the sum of all the decisions we make.

We've all encountered moments when we know we should do something, but are too lazy or lack the courage.

Hitting the gym instead of sleeping in

Going for coffee with a new person instead of watching TV

Taking on a growth project instead of playing more video games

Taking the job interview instead of staying complacent in a job

Speaking up in a meeting instead of passively sitting back

Sharing your art with the world instead of staying in your safe space

Asking for a promotion or raise instead of avoiding hard conversations

Any of this sound familiar?

I spend a lot of time thinking on the margin where these decisions are made.

Sometimes, all it takes is a gentle nudge to overcome laziness and fear.

Here are six ideas I keep in mind when I need that nudge:

Minimize potential regrets

Engineer your own luck

Step into the arena

When in doubt, ship it

A closed mouth doesn’t get fed

Make uphill decisions

Minimize potential regrets
Jeff Bezos, Founder of Amazon, has a simple mental model for making tough decisions.

He asks himself the following question:

”In X years, will I regret not doing this?”

Then he takes action.

The next time you have an opportunity to take on an impactful project at the expense of your temporary free time, ask yourself: “In 5 years, will I regret not doing this?”

“I knew that when I was 80 I was not going to regret having tried this. I was not going to regret trying to participate in this thing called the Internet that I thought was going to be a really big deal. I knew that if I failed I wouldn’t regret that, but I knew the one thing I might regret is not ever having tried.”

— Jeff Bezos

Engineer your own luck
Luck doesn't have to be passive. You can engineer your own luck by maximizing your chance of serendipity.

‘Getting lucky’ is the result of an:

Attitude (belief or mindset)

Opportunity (a good thing coming your way)

Action (doing something about it).

Consider the Luck Razor: If stuck with 2 equal options, pick the one that feels like it will produce the most luck later down the line. (e.g. Instead of watching Netflix, go out for drinks with a stranger).

Step into the arena
I stole this idea from Sahil Bloom, who stole it from one of Theodore Roosevelt’s most widely known speeches.

Being on the sidelines is easy. It’s comfortable and it’s the safe option. It’s tough to step into the arena — to be vulnerable, exposed, and open — but that’s where growth happens.

Be the man (or woman!) in the arena.

"It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better.

The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat."

When in doubt, ship it
It takes time for the quality of your work to catch up to your ambition.

Your first article, piece of artwork, podcast, product… will likely be subpar.

But as the Silicon Valley ethos goes: When in doubt, ship it.

By shipping early, you get more feedback, and as a result — more opportunities to iterate on your work.

In the Marshmallow challenge, MBA students and Kindergarteners were given 18 minutes to build the tallest possible structure with marshmallows and spaghetti. Guess who won? Kindergarteners.

Once the timer went off, Kindergarteners immediately began building structures. Through rapid iteration, they were able to quickly understand what worked and what didn’t. The MBA students were most likely stymied by analysis-paralysis, overthinking the problem, and failing to test sufficiently.

A closed mouth doesn’t get fed
Be your own best advocate. Learn to identify what you want and ask for it.

The worst thing that can happen is a ‘no’ and you’re back to the status quo. (wow, that rhymed)

And if you receive a 'no,' it’ll just thicken your skin. Rejection therapy has long been used to help folks enhance their emotional intelligence.

Make uphill decisions
We’re wired to take the path of least resistance.

Instead, encourage yourself to do the hard things and make uphill decisions:

When presented with two options, pick the one that’s more difficult in the short term.

We all desire to achieve something effortlessly, yet the effort paradox holds true in that it takes more effort to make something appear effortless.

Do the hard things.

An antidote for inaction
Keep these ideas in your toolbox for the next time you're faced with a seemingly difficult decision. Especially, if you believe that laziness or fear is driving you in one direction.

I’ll leave you with this:

“Hard choices, easy life. Easy choices, hard life.”

— Jerzy Gregorek, Olympic Weightlifting Champion