To start the year, I am writing a series of posts around the “the career of life” series. In these posts, I focus on experiences and skills that help us succeed in our careers, but also and perhaps more importantly, at being human.
Last year, we had a pandemic, an election and tons of racial and political unrest. It is fair to say that for many of us 2020 wasn’t what we expected.
But despite all its difficulties, 2020 was a year that allowed me to learn and grow as a professional and individual. The most likely reason for this is that I came into the year with the goal of taking smart risks. These risks, I am sure helped me speed up the pace of achieving my life goals.
These risks included:
- Leaving a stable job where I had built a solid reputation as a good performer
- Ending or changing lifelong relationships that no longer served me (or them, to be honest)
- Traveling overseas to complete a real estate transaction
- Having a series of earnest conversations about race with senior management (including the CEO) at Bloomberg.
- (This was before George Floyd and current streams of race consciousness so I truly had to think this through)
Many of these risks paid off, others didn’t. But in the process, I understood the meaning of a few things:
1st: The greater the risk the higher the rewards
2nd: To take risks you have to put yourself in the position to do so
3rd : Taking risks is one of the greatest way to growth
More and more I notice that last point is extremely important.

See changing one’s life in a meaningful way is almost impossible by taking the known or safe path. As a result, most risk, and the growth that comes with it, come from moving away from familiar habits and patterns. As soon as you start doing things differently than in the past the more the likelihood of failure increase. But that same change also comes with the likelihood of obtaining a greater upside.
Taking a risk could be as simple as “having a difficult chat” or making a great financial investment where results are not guaranteed. And yet, I noticed that for me, both bring the same level of anxiety.
Consequently, I want to share a few tips have helped me increase my risk-taking and reduce the amount of angst:
1. Quantify the downside: What is the probably that the worst could happen? For example, if you have an honest conversation with an authority figure, what is the chance that you actually would get fired or worse? If you were to get fired, what would be the worst that could happen? What is the chance that you would never eat again? Really, try to put a number to it! 10% 5% 90%?
2. Quantify the upside: What can you gain by taking an specific action? A promotion, more money, the love of your life? This should incentivize you. Like before, you should start thinking what is the likelihood of this happening? 10%, 5%, 0%?
3. Practice with small risks: Instead of always making big jumps, can you start small? Could you make a smaller investment? Could you have smaller stakes conversations that get you ready for the big one? In my case, I have taken to playing low stakes poker as a way to start practicing the probably of lost and start differentiating between small and big risks
4. Are you able to hedge? In finance, you can reduce risk by buying options that are contrary to some of your main positions. What can you do in your life so you feel more comfortable with risk. Can you save more money? Can you put a support system in place? Can you gain more information somehow?
5. Quantify the cost of doing nothing? Many of you may feel different, but for me this was the true motivator. It is unnaceptable for me to stay with the status quo. If I have enough information to know that I will not be happy if things stay the same then that is enough for me to get going.
Often times, for me staying put and not growing is the absolute worse that could happen.
I hope the above gives you a bit of incentive to take more risks in your life.I also hope that the new year brings you the insight and motivation you need to achieve your goals.
Like what you read? Feel free to follow me on twitter @alexmontas or on Linkedin for more of my musings.

