How to get lucky

Ever since I was old enough to understand the meaning of the word, I’ve considered myself lucky. By that I mean someone who generally has good things happen to them and catches a few big breaks along the way. While the dictionary definition of the word luck hints at a force beyond one’s control, following the rules below will increase your chances of hitting “greenlights," as McConaughey would say:

Be an optimist. You cannot get lucky - or even recognize it when it happens - if you do not have an optimistic outlook. People who are constantly victimized and think the world is out to get them are never lucky even when they are. They are often a drain on others. They do not put themselves in position to capitalize on opportunities that appear. You want to view the world from the lens of someone who is in control over their own destiny.

Never assume. Every day, many times per day, we make judgements about different situations we are presented with. Many times we turn out to be wrong. Lucky people do not take action based on assumptions. They do not jump to conclusions and get stressed out by them. They test, validate and make decisions once they have complete information.

Actually do assume (the best in others). As Hanlon's razor states, "never attribute to malice that which is adequately explained by stupidity”. I take a slightly different tack on this and assume that one's colleagues generally do not have a goal of creating more work for those around them. I am surprised by how often people approach professional situations with closed-minded skepticism. I like to approach interactions with the assumption that people want to get the job done as efficiently as possible.

Work hard. Probably the most important prerequisite to getting lucky is to simply work hard. I had a boss early on who liked to use the maxim “never let your boss beat you to the office.” I often failed at this simple task, but showing up and outworking those around you is something that anyone can do and it has stuck with me.

Accept every opportunity. Early in your life and career, you should accept every opportunity that comes your way. I have been involved in many companies and organizations that were not immediately lucrative but led to other opportunities down the road. Eventually this will flip and you will have to learn to say no more often than yes and be more precise in your criteria for evaluating things, but this is a good problem (and make no mistake, it will be a problem at some point) to have.

Be open. Optimists tend to be open to new opportunities and connections. I think this is a prerequisite to being in position to capitalize on things that may come your way. If you approach inbound opportunities with a skepticism, it will come across clearly in your communication.

Be yourself. Perhaps the most cliche item on this list, but one that has served me well since I began to put it into practice. Posturing, trying to seem smarter than you are, trying to be a chameleon in every situation is incredibly tiring. It also ends up pulling you in the wrong direction as people will draw you into situations that they think (based on your behaviors) are appropriate or relevant for you. Just be open, honest, empathetic and do good work and the rest will take care of itself.

Growth mindset. Nothing is fixed. Over time, your skills will improve, even more so if you make time for deliberate practice. The things that you may not consider yourself good at today can easily be strengths in the future if you take the time to make it so. The worst thing you can do is assume that the strengths and weaknesses you have today will be the same 10 years from now.

Manage expenses first. Be cheap, especially with business expenses. It is easy to sign up for recurring charges and forget about them, to make hires that are not yet necessary, to plan for best-case outcomes. If your overhead is low to begin with, you’ll have much more flexibility in your decision making. This is also true in your personal life - I optimize major decisions around 2 things: net income (does it bring money to me or away from me) and flexibility (does it increase or decrease my options). If it fails either of those tests, it is a no.

Be flexible. Things are not always going to go the way you want them to. When my wife and I were planning on leaving New York to travel and work internationally, we submitted a request to our co-op board to sublease the apartment we owned. Despite the bylaws stating that this was permissible, they rejected our request outright and refused to provide any rationale for their decision. Frustrated but unfazed, we sold the apartment within a few weeks and hit the road. Two years later, COVID-19 hit, decimating New York in many ways, including the residential real estate market. What appeared to be a major setback turned out to be the best thing that could have happened.

Have fun. As Jerry Seinfeld has infamously said, life is long. We spend a great deal of it at work. Given that not all of us (myself included) are lucky enough to end up in our dream job, finding ways to enjoy each day is important. If you can’t find enjoyment in the daily grind, in delivering excellent work and interacting with others, you are likely going to experience some miserable decades in your life.

Don’t take yourself too seriously. Life is going to come with ample challenges. You are going to be tested personally and professionally. If you are someone who believes they can do no wrong, or that others aren’t on your level, people will see through that and talk about you behind your back. To me, this is one of the saddest things to see, especially in the workplace: someone who thinks they are beloved but are reviled because they lack empathy and see themselves on a higher plane than those around them.

Be grateful. One of the most powerful mind hacks I’ve ever learned is to simply think of a few things you are grateful for in the midst of stress or despair. It is impossible to feel both emotions at once and as soon as you put some concrete thinking around what you are thankful for, you will feel better. Even more impactful is to do this daily, even when things are going well, which I find creates a snowball effect in lifting your entire outlook.

I’m writing this during the Thanksgiving week in the US and I am thankful for a challenging year. For being able to spend time, however limited, with family. For the two years of travel I experienced prior to the pandemic. For the freedom to write this. For those who have sacrificed and continue to sacrifice to allow me that freedom. I will spend some time each day thinking of other examples.