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How To Get Lucky, Or That Time Someone Took A Chance On Me

How To Get Lucky, Or That Time Someone Took A Chance On Me

Liston Witherill
Liston Witherill
5 min read

How do you become successful in your field?

I wish there were an easy, one-size-fits-all answer. Here’s what I’ve learned: you need someone to take a chance on you. Maybe multiple someones.

Ryan Holiday, an author and marketer, got his break when he worked with author Tucker Max. The two of them staged a boycott of Max’s book, which drummed up considerable publicity and book sales. Holiday then worked with best-selling author Robert Greene), and later became Director of Marketing at American Apparel. He now runs a marketing firm and book services business, and has published nine books of his own.

Would Holiday be where he is without first knowing Tucker Max?

Perhaps not, or perhaps it was all fated to fall into place this way. Who knows.

It’s tempting to examine successful people and reverse engineer their success in hopes of repeating it. That may work in some cases, and not in others. But there is one pattern shared by many successful people I’ve either known or observed:

  1. They knew one or more pivotal people who put them on a new trajectory
  2. They attribute a large percentage of their success to luck

Finding those pivotal people seems to be a part of making your own luck. Which is to say that you can’t succeed alone, and you need to create your own luck.

You Need Help, I Need Help

We all need help. It may be possible to succeed without it, but it’d be the rare exception.

If you’re running a business, you need clients.

If you have a creative pursuit, you need fans.

And if you’re looking for a new job, you need an employer.

For you to progress, you need these people to take a chance on you. Hoping that they’ll take a chance on you isn’t a strategy, though. The only way that ends well is through dumb luck - no different than winning the lottery.

Someone recently took a chance on me, and that person has changed the trajectory of my life. Here’s what happened.

Well That Was Lucky

I was working on a slow afternoon when a new message popped onto my screen. Someone on my website wanted to take my sales training and had some questions about it.

We had a phone meeting to discuss what she needed and how I might be able to help. Her company is bigger than any client I’d had before: a public company worth $7 billion with 5k employees. I’m not a corporate guy. I told her as much, knowing that she might say “thanks, but no thanks.” She didn’t.

A few months later, I was training more than 50 people at her company.

She took a chance on me. I didn’t have the perfect track record of working with companies exactly like hers. She knew that.

And without an existing track record of work with big companies like hers, the risk was even greater. Still, she took it, and it’s worked out well for both of us.

How did I get so lucky? To answer that question, let’s first look at how luck works.

The Dimensions of Luck, Explained

If we need someone to take a chance on us, it begs the question: how can we get lucky? We could hope for luck, but we can also make some.

It’s instructive to look at the dimensions of luck to see how we can get lucky - or luckier. Marc Andreessen suggested there are 4 types of luck:

  1. Chance I - Blind Luck: great things happen totally by chance
  2. Chance II - Motion: you do a bunch of stuff and, through applied but unfocused action, something good happens
  3. Chance III - Recognizing Good Fortune: you identify an opportunity because you’re the only one equipped to see it
  4. Chance IV - Directed Motion: you recognize opportunity and direct your motion to attract and seize on it

Let’s simplify the definition a bit with just two dimensions: effort and intention. The more effort you apply, the more likely you are to find opportunity, and the more likely it is to find you. You’re also more likely to get lucky if you’re intentional and strategic in applying your effort. Combine the two, and you’ve maximized your chances of getting lucky.

Here’s how I think about luck:


Focused Luck. That’s your best shot at getting someone to take a chance on you.

Applied effort and intention will attract the right people. Whether they take a chance on you or not is up to them. But the more effort and intention you create, the more like you might make, too.

The person taking a chance on you will face some risk. And of course they will: the less proven you are, the more risk they take.

But if you find yourself getting lucky through Focused Hustle - or Chance IV luck - then someone is taking a small risk.

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In an interview on How I Built This, Tobias Lütke of Shopify attributed 90% of his success to luck. He’s being modest, but he recognized the timing, relationships, and chance events that needed to fall into place. Before raising investment, he had thousands of businesses using Shopify stores and proven methods of marketing. Investors took on low risk when they invested because of Tobias's Focused Hustle. Sure, he had the right people involved and he got lucky, but he made a lot of that luck himself.

More Specifics On How I Got Lucky

I left out a few things about how I got someone to take a chance on me. Here’s what else you need to know.

I record and publish a sales podcast every week. No one pays me to do it, and no one pounds down my door if I miss a week. I’ve spent over $10k on growing and promoting the podcast.

My client first discovered my podcast through an ad I bought. She became an avid listener, and eventually my services lined up with her internal priorities. That’s when she visited my website and reached out.

Once we began talking, there was nothing inevitable about us working together. In fact, there was inertia working against me, for safer training options in the market. I persisted. It also helped that I provide sales training, and could show her how I approached my own sales process.

Over the course of 5 months of persistence, checking in, and repeated effort, we finally reached an agreement.

All of these factors made the decision a lot less risky for her. My intention was directed, and 100% of my effort went into that single direction. That’s why she took a chance on me.

It helps to create as much of our own luck as we can.