Live Life and Make Choices Like You’re a Startup CEO
Our lives are a series of choices, some of which we make ourselves and some of which are made for us.
In the end, we’ll all look back on our lives and the choices we made and judge whether they were good or bad and what they add up to.
It’s like we’re all driving a train that won’t stop, deciding which turns to take with nothing more than a vague idea of where we’re going or when we’ll get there. So how can we make the right choices?
Rolling the Dice
I landed in Buenos Aires at 3 am on January 3, 2010, with a backpack and no return ticket. I had less than $5k in my bank account, a reservation at a hostel and no friends in the city.
The receptionist at the hostel was a short, curly-haired porteño with a beard. Eyes half shut, he showed me to my room and left me there in the dark. Five sleeping occupants lay on the bunk beds that filled the room, snoring in foreign languages. The only free bed was all the way at the top, and there was no ladder.
I hoisted myself up, lay down fully clothed, and wondered what the hell I had gotten myself into.
I’d graduated with a history degree less than a year earlier than the day left the US with a one-way ticket to South America. With the Great Recession in full swing, the only full-time job I could find was at Starbucks. I came to Argentina to teach English and improve my Spanish.
It was a major choice — lots of people looked at me like I was insane when I told them what I was doing. I’d done research, found a school that offered a well-reviewed TEFL course, spoken to other ESL professors living abroad.
For a move like that, how much research is enough? There was no way I could ever know enough to be sure I’d be successful, that I wouldn’t come running back to the US with my tail between my legs, having spent all of the money I’d saved working at Starbucks for eight months, with nothing to show for it.
Yet my gut told me it was the right choice. That I was poised on the edge of an adventure, that I needed to roll the dice. So I went as soon as I’d saved enough money, with no apartment lined up, and no real backup plan for what I’d do if I failed.
The first week I was there, I met with some prospective roommates in a large shared apartment. One of the Brazilian guys who lived there poured me a beer from a liter jug of Quilmes. He had a quick and easy laugh and I felt like he’d be a friend for me in a strange city.
Seven years later, I was a groomsman in his wedding in Sao Paulo. While I was there for the wedding, I reconnected with the woman who I just married this last August.
I ended up staying in Buenos Aires for two years. I made dear friends, learned a lot about myself, gained maturity, made mistakes, and figured out a few things I didn’t want to do.
Now, I speak Spanish fluently and am well on my way to learning Portuguese. My experience living abroad is something that I draw upon daily. Moving to Argentina was one of the best decisions of my life.
Sometimes, we need to make a gut choice, without having the complete information. Because in reality the information you have is never complete, and that’s ok.
Saying Yes is Saying No
Choosing something means more than just saying yes to one option — it also means saying no to a lot of other things.
Opportunity cost is the price we pay when we commit our resources to one thing. Those resources are no longer available for something else, which means we can miss out on opportunities that might have otherwise been available.
And we have to learn to say no to a lot of things before we’re able to say yes to new things. In his book Essentialism: The Disciplined Pursuit of Less, Greg McKeown talks about focusing on the “vital few”. Deciding what’s truly important and honing in on that.
It’s easy to slip into a reactive mode where we make choices as they come up. Our days become a chain of little tasks and before you know it the day is over and we haven’t moved the needle on any single priority, we’ve just kept the ship upright.
McKeown posits that we need to focus more on momentum — instead of moving a millimeter in each direction, move in one direction towards what’s really important.
That means being deliberate about the decisions we make, and acknowledging when we are making decisions. Which is basically always. When we accept that meeting request at work, we’re choosing to do so without asking why or pushing back.
When we pick up our phone and read that email that comes in after work hours, we’re choosing to stay connected to our jobs rather than spending time with friends or family.
When we slump on the couch and turn on Netflix instead of picking up a book, we’re choosing mindless entertainment over enrichment.
None of these choices are bad necessarily. What’s important is to remember that they are choices, and to not make them on autopilot.
Knowing Yourself Is the Most Important Thing
None of this matters if we don’t truly know ourselves and what we want out of life.
We can’t seek our true north if we don’t know in which direction it lies. We can’t build momentum and focus on our priorities if we don’t have priorities.
I once made a bad career decision. I left a job I loved and took a new position that had a lot of benefits — literally, it had great benefits, higher pay, and was an opportunity to build a skill that I thought I really needed to advance my career.
On paper, it was the right choice. But if I had truly looked into my own heart and known what was most important to me, I would have seen that I was giving up a leadership role, where I managed others and made important strategic decisions for a job that was much more tactical and self-reliant.
It didn’t fulfill me. I could feel that I was building the skills I thought I needed, but I just wasn’t happy.
Now, I understand that what is important to me is being in a position of leadership. I love the science of management and motivating others. I thrive on feeling like an entrepreneur, building processes and tweaking them to constantly improve.
That choice I made was wrong because I didn’t know what I really wanted, but it also helped me learn about myself, which was crucial for future decisions I had to make.
Live Your Life Like an Entrepreneur
In the book The Lean Startup, which is basically a bible for the modern entrepreneur, Eric Ries says that the goal of a startup is to figure out the thing that your customers want to pay for as soon as possible.
In other words, you don’t start with the perfect product, with all the right answers in hand. Instead, you have a vision of how you want to impact the world and undergo and iterative, experimental, scientific, learning process where you keep refining your product and process until it works.
You never “get it right”. You’re always innovating, changing and tweaking.
You’re informed by your goal, but leave yourself room to pivot and change to continuous refine how you are getting there.
That’s how we should all make choice — unafraid to make mistakes and learn from those mistakes, having calculated the risks to make sure they won’t be disastrous and take us out of the game.
