How to Get Lucky and Change Your Fortune

Can you really improve your chances of getting financially lucky?  Turns out you can.

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As Luck Would Have It:

I missed my flight.  I missed my flight because I got off the plane at 12:05pm.  I got off the plane because mechanical issues had grounded us for an hour and a half, which means I would be late for my 3:30pm call if the flight didn’t leave by 12:15pm.

So I ran.  I ran 15 gates down to ensure a seat on the later flight.  Just as I arrive at the other gate, they call me back to re-board.  It was 12:09pm when my futile knocks fell on the jet bridge door.*

Luck had gotten me again.

With time to spare now, I decided to do the prep work I’d planned to do on the plane.  I checked my email to run through the meeting itinerary when I noticed something.

The call had been moved up to 2:30pm.  Had I gotten on that earlier flight, I would’ve missed the call completely.

Is it Better to be Lucky or Good?  


It’s better to be good at being lucky.  

Luck is a force that brings you good fortune or adversity.  And it feels largely outside of your control.  But it turns out that you can improve your luck.

The hedge fund manager and author, Nassim Nicholas Taleb, calls big luck events “Black Swans**” (unexpected events that change your worldview) and he’s thought about luck more than just about anyone else.

Because Black Swans and luck share similar characteristics, I will lean heavily on Taleb’s book, The Black Swan, to provide us insight on luck.   

The Lucky 7:  Tips to Understand and Improve Your Luck

1. Don’t Overestimate the Power of Bad Luck:

You’re going to experience two kinds of luck:  “Good” and “Bad.”  Luckily for you, bad isn’t so bad.

“We grossly overestimate the length of the effect of misfortune on our lives. You think that the loss of your fortune or current position will be devastating, but you are probably wrong. More likely, you will adapt to anything, as you probably did after past misfortunes.” – Nassim Nicholas Taleb, The Black Swan

Think about the worst thing that happened to you in the last 2 years.  Sure, it felt really bad at the time. You thought you’d never get over it.  But chances are, you did.  For the overwhelming majority, bad luck won’t kill you.  You’re more resilient than you think you are.  And because of your pluck, even though today is bad, you give yourself a fighting chance at better luck tomorrow.

2. Believe in Your Luck:

Lucky people are more lucky.  According to psychologist Richard Wiseman at the University of Hertfordshire in England, people who describe themselves as lucky:

  • Are more willing to meet people and keep in contact, maximizing their chances to have a lucky encounter.  
  • Are more relaxed.  So they “notice chance opportunities, even when they’re not expecting them.”  
  • Are open to new experiences.  They travel more, welcome unique opportunities, and like unpredictability.  

But, if you think of yourself as unlucky, you’ll dwell on your bad luck.  You’ll be afraid and avoid new people, new things, and new experiences.  You will have minimized your chances at getting lucky again.

3. Interpret Your Luck:

Here’s the thing.  Most events in our life can be lucky or unlucky, depending on how we interpret it.  Take something that happened recently.  I dropped a knife on my foot last weekend.  It sliced into my foot and left me with searing pain, a slight limp, and inability to exercise.  But, even though blood poured out profusely, I didn’t need surgery.  And my guest for dinner that night?  Just happened to be an ER doctor.  So…was I lucky or unlucky?

If you think I’m lucky, would you like to have switched places with me moments before the knife fell?  If you think I’m unlucky, can you imagine what else could have happened?

Luck is the narrative you tell about your life.  Wiseman adds that those who believe they’re lucky “turn bad breaks into good fortune.”  Lucky people expect good things to happen.

Luck is an unexpected event.  That you cannot control.  But what you can control is how you interpret it.  In many ways, those who view their situations as lucky also seem to be the type of people who choose to be grateful.  Coincidentally, grateful people and self-described lucky people tend to be happier.

(I get into this more and share the story of my luck below.)

4. Give Yourself a Chance to Get Lucky:

“I’m up all night to get lucky” – Daft Punk

“The reason free markets work is because they allow people to be lucky, thanks to aggressive trial and error, not by giving rewards or “incentives” for skill. The strategy is, then, to tinker as much as possible and try to collect as many Black Swan opportunities as you can.” — Taleb

This makes sense.  Quit early and you disqualify yourself from winning the game.  Stop tinkering after some early failure and you’ll miss out on potential discoveries.

In many ways, this is the law of averages.  In his book, Originals: How Non-Conformists Move the World, Wharton professor Adam Grant notes that highly successful people just try more things. He uses Shakespeare and Picasso as examples.  Each produced a very large amount of work, many “average” and not distinguishable from peer artists.  But the few pieces that we do remember define how we think about them.

Grant writes that we assume that we should trade less quantity for higher quality.  But in fact, quantity is the most reliable predictor of quality.

So try enough things, and chances are you’ll get lucky on one of them.  But, try the right things and you can get even luckier.  How do you identify those things?

5. Understand the Game — the 3 Rs:

Most people don’t stop to figure out the game they’re playing (most people don’t even know they’re in a game).  They’re passive participants.  They don’t take time to figure out The 3 Rs:  Rules, Rewards, and Risk.  The great majority of us work for someone else, so let’s look at that game:

  • Rules:  Do what you’re told.  If you perform your objectives, you stay in this game.  If you don’t, you’re disqualified (fired).
  • Rewards:  If you play this game well, you can get promoted.  From sites like, you can generally know your potential rewards by looking at the compensation of the levels above you.  Some careers have very high rewards, like finance and law.  Others, not so much.  And within each job, the career ladder is different.  So your potential reward not only varies by amount of dollars but by odds.
  • Risks:  You risk getting fired.  You also risk your firm going out of business.  If you’re in a cyclical industry, during a down point in the cycle, you might get fired along with many others.  So you’re competing with hundreds or thousands of players for very few, if any, jobs, since almost no company in your industry is hiring.  So the risk in your game is not unemployment — it’s prolonged unemployment.  Or, it’s the loss of time, with years of your life spent trying to earn rewards that you haven’t yet realized aren’t worth it to you (especially for those of you who are in stressful, high paying jobs that require excessive hours.  You risk under-developing your friendships and life outside of work.  High pay sometimes blinds us to the true risk.)

If you don’t know the rules, the rewards, and the risk, you have no strategy (or a very poor one).  If you do know the rewards and they’re not that exciting to you, then your potential luck is minimal in the area where you devote most of your waking hours.

Time to find a new game.

In other words, if you’re taking Taleb’s advice, it means that your tinkering is not for ways you can get that promotion or raise.  It means that you tinker with finding new jobs with higher rewards, acquiring new skills, or trying out side-hustles.

(If the rewards of getting promoted are worth it to you, read about how to land that promotion here.)

6. Gamble Better — Limit Your Risks:

“This idea that in order to make a decision you need to focus on the consequences (which you can know) rather than the probability (which you can’t know) is the central idea of uncertainty.” – Black Swan

See that?  Don’t focus on probability of your getting lucky.  Focus on the consequences — in other words, your risk.

Contrary to belief, successful entrepreneurs don’t run to risk.  They run from it.  They are great at mitigating their downside.  Malcolm Gladwell writes in The New Yorker:

“In a recent study, “From Predators to Icons,” the French scholars Michel Villette and Catherine Vuillermot set out to discover what successful entrepreneurs have in common….The truly successful businessman, in Villette and Vuillermot’s telling, is anything but a risk-taker. He is a predator, and predators seek to incur the least risk possible while hunting.”

Gladwell uses the example of Ted Turner, who bought a failing TV station.  Everyone, including his lawyer and accountant, advised Turner not to buy it, viewing it as too risky.  But he used the losses to offset the tax gains in his highly profitable outdoor billboard business.  He also used his blank billboards (around 15%) to advertise for this station.  Finally, he paid for it with a stock swap structured in a way where he didn’t have to put a penny down.

This transaction eventually led to the founding of CNN, TBS and TNT.  It also helped him buy the Atlanta Braves and made him a billionaire.

If you mitigate your risks well, you minimize the chances of bad luck while preserving your chance to get lucky.  This low risk, high reward dynamic is the recipe the most successful entrepreneurs and investors used to get really lucky.

So how can you mitigate risks in your life while trying to get financially lucky?  Make a map.

(So what’s something you can do that has low risk but high rewards?  Blogging.  Find out why and how here.)

7. Make a Map:

“(J)ust as we tend to underestimate the role of luck in life in general, we tend to overestimate it in games of chance.” – Nassim

The luck you care about is really about future luck, not past. And future luck is affected by your decision making, which is further affected by your planning.

In Make Your Own Luck, authors Eileen Shapiro (a former McKinsey & Co. consultant and current Hillcrest Group, Inc. President) and Howard H. Stevenson (Harvard professor and founder of the multi-billion dollar hedge fund Baupost Group), encourage us to start with the end and work backward.  

(Interestingly enough, I had come to this same conclusion even before I had known about Make Your Own Luck.  I cover my thoughts about it here:  Why Living in Reverse is the Key to Moving Forward)

Why start with the end?  Because it helps to think about your path and outcome before you place your wager.  

But if you start from where you are and build your route forward, then each step forward could have multiple options.  For example, a route forward with 5 steps where each step has 4 options renders over 1,000 potential outcomes by the final step.

  • Step 1:  4 options (1 x 4)
  • Step 2:  16 options (4 x 4)
  • Step 3:  64 options (16 x 4)
  • Step 4:  256 options (64 x 4)
  • Step 5:  1,024 options (256 x 4)

No wonder we get paralyzed thinking about the future!  We’re overwhelmed by the choices.

But, as Shapiro and Stevenson write, “Every option you prune at the beginning of the path allows you to cut all the multiple future alternatives that would’ve grown from that initial possibility.”

And the power of working backward is it reduces the outcome to one option.  And while the steps in between the end and today may have different options, knowing your starting point and ending point anchors you in both directions, helping you limit your options in between to the most rational and realistic.

Now, because you’ve pruned your options to a more rational and realistic path, you can do your “3 Rs” analysis of each step.  And because you better understand the risks, you can figure out how to mitigate them.  

That said, don’t forget to be flexible to enough to allow for changes and unexpected events, since that’s the nature of black swans.  In those cases, hit the re-route button and work backwards from your new position.

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Decades of Luck:

I’m a lucky guy.  I have been my whole life.  Here are the five major moments:

  • When my parents escaped their country on an overstuffed fishing boat, I cried.  I cried so much that I put the entire boat in danger of alerting pirates at sea.  My dad had to come over to help calm me down.  Right then, an unusually large wave hit and tipped the boat.  The people in the section of the boat where my dad had been sitting were washed away and lost to the sea.
  • I was a shy, awkward kid.  I was bullied.  Adults called me stupid.  For some reason, after a few weeks into 3rd grade, they moved me into the gifted and talented class despite my poor grades.  In this class, I met David, who befriended me even though I never said a word to anybody.  He taught me how to play sports.  He invited me to church.  That one invitation changed my entire world.
  • After interviews at other, lesser firms, that went nowhere, I had a promising one with a prestigious investment bank on the top floors of a world famous building.  They didn’t want me.  I was rejected and dejected.  I was living in a hostel in Spanish Harlem and down to my last dollars.  So I pleaded hard for it.  Didn’t help.  Months later, planes crashed into that building and its twin, taking out the floors underneath where I would have worked.
  • My longtime girlfriend shattered my heart.  I was depressed for months.  Until it opened my eyes to a good friend.  She’s smarter, more attractive, more accomplished, and better with budgeting than I am.  We now have 3 children together.  Did I mention I’m a lucky guy?
  • I was being laid off in the worst recession in many decades, with my first child on the way.  But before they could fire me, I found another job with better hours.  I invested heavily into the recession and enjoyed the best returns of my life.

You think I’m incredibly lucky because I set the narrative that way.  I could’ve just as easily focused on the moments of misfortune in my life and let that dictate the story I tell you (and myself).

Focus on and be grateful for your moments of good luck and you’ll feel and be fortunate.

You’re So Lucky:

Many things don’t go according to plan.  If it did, you wouldn’t be reading these words.  Instead, you would be on your private jet en route to your private island.  Instead, life gives us the unexpected.  And we rationalize it as luck, either good or bad.  Whatever you get, don’t forget:  Your success or failure isn’t because of luck but the decisions you make to get luck.

You also wouldn’t be reading these words because you shouldn’t exist.  I’ll let the quotable Nassim Nicholas Taleb elegantly conclude us:

“Imagine a speck of dust next to a planet a billion times the size of the earth. The speck of dust represents the odds in favor of your being born; the huge planet would be the odds against it. So stop sweating the small stuff. Don’t be like the ingrate who got a castle as a present and worried about the mildew in the bathroom. Stop looking the gift horse in the mouth—remember that you are a Black Swan.” 

*This is how crazy I am.  The unattended agent’s desk phone rang.  I reached over to pick it up.  Before the person on the other line could complete a sentence, I interrupted to tell them that I was standing outside the jet bridge and to let me in.  No luck.

**Why is it called a Black Swan?  Imagine you’ve grown up being told all swans were white.  Every encounter with and every picture of a swan you’ve ever seen was white.  Then one day you pass by a lake and see a black swan.  You have to revisit everything you’ve ever believed about swans.  


  • Luke April 3, 2017 at 1:09 pm

    Loved your header for the article. Interesting read thanks for sharing.

    • JT April 5, 2017 at 12:05 am

      Thanks for dropping by, Luke! Hope you find it useful.


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