Bargaining with risk

One of my favorite sayings is ‘choose your favorite flavor of sh*t sandwich’. It encompasses better how we should spend our time than to ‘follow your passion’.

Maybe I am just enjoy pain, but often to engage in an activity we find meaningful will involve a degree of discomfort.

It comes down to a choice of do I take the pain now, or do I take it later. It is the choice of getting your ass in front of your computer to research that business idea or lying on the couch dreaming of being Elon Musk.

But given a definite choice to realize your dream, you must endure a certain number of sleepless nights, quantifiable weekends at your desk working and so many hours of sacrificed social events, many of us would opt to work for our dreams.

Namely, if we could quantify the price, we can make a rational decision and decide to make the trade. But the best things in life are rarely rational or transactional in nature.

And so, we look back at those once dreamed of goals and ask ourselves why we gave up on them? Did we try and realize it wasn’t for us? Or did we get scared of failure?

We want certainty, we want to know that if we put in the effort there will be a reward for it. If we make that investment, we want that return on our capital.

My mind still has that wiring, but over the years I have become more risk tolerant, but still have a way to go.

A lot of what I found, is that you must take multiple risks to start seeing a return. Your first effort will likely fail, that one idea will come to naught, that stock will lose 50%.

It is the learning tax. That price of learning can be too much for many of us and all those uncertainties come flooding back, so we get out while we can.

We can also satisfy ourselves that we gave it a try.

But we are focusing on the downside of our dreams and the upside of the security and certainty of what we knew before.

Logically that is how we are wired. Emotionally, we regret what we don’t do much more than what we do, do. We are left with that aching feeling, no matter how much we rationalize it.

Following your dreams is a journey not a destination and we do not know what opportunities will open-up on the way. New contacts, new learning, new experiences for us to adapt our viewpoint of what we really want.

Following your dreams or goals is giving you permission to try different things.

I remember when I was at Tesla, and serious problems hit, we were always under the crunch to get things fixed rapidly.

My initial mindset was to investigate the issue, pick the most likely variable to change, collect data, analyze the results, and see whether you had made an improvement.

Wow, so slow . . . and very often led to failure at the first try.

My mind was opened to brainstorming a diverse set of solutions and trying them all at once and iterating from there.

You learned far more quickly and whatever didn’t work you could peel off until you converge on the best possible course of action.

Giving yourself permission to chart that new path is not fixed, it will allow you will try new things, meet new people and encounter many ups and downs.

Some of us, try to hustle this process, we work our day job, we try to maintain our existing commitments and look for spaces to fit our dreams in between.

This can be okay for a while if you have clear steps, and you can use the compressed time as a pressure point to motivate you into progressing along that path.

At some point, you will want to expand to give yourself more space to try more things to realize the true direction you want to go.

Your life as it is, is not structured in a way to put your goals and dreams front and center.

I remember watching Esther Perel in an interview making an observation when having lunch at a restaurant on a Monday and seeing all these people in energetic conversations and wondered how many were actually with their partners rather than their work colleagues?

Her point was that often we give the best of ourselves to our obligations, and we end up giving our partners, or ourselves what is leftover.

Just like you cannot hustle a relationship, you cannot hustle your dreams, our motivation will get too depleted. We would miss that training session, then the following week maybe two and soon your goal falls out of your grasp.

However, if your goal became the most important thing in your life for a while, you could give the best hours of your day to it. Then rest, relax and enjoy to ensure there are enough reserves for the next day.

This is why taking the risk, is more important than trying to hustle something through. It maximizes your chance of success, even if it is in a way you did not envision, because the risk you take is you saying ‘I am giving myself priority for this’ no matter what the discomfort.

And taking those risks will determine how you will look back on things, by being the dreamer who did not go for it, or plucking up the bravery to put your dreams front and center despite the risk and uncertainty.