Are some freelancers just lucky? How to think about luck, effort, and character

Reflecting on how he landed a series of anchor clients, a writer named Hank told me, “I feel like I've gotten lucky.” Luck isn’t a strategy any of us can copy, but let’s see what closer scrutiny of Hank’s experiences as a freelancer word turns up before we look at the word “luck” itself from several angles.

Hank had approached me about freelance business coaching, but rather than pitch him on working with me, I took my usual tack and asked questions to better understand his thinking and situation. What were his goals? What were his roadblocks? How had he picked up new projects in the past?

His answers to the last question were telling:

• “I was testing out persistence at the time.”
• “I immediately found another client just because a friend of mine passed them my way.”
• “I've also been trying to Google keywords that I would want to write for and just emailing the people, the sites ranking for those, asking if I could send them a sample or write for them.”

Most of us think of persistence as something that some people have more of and others, less of, a fix quantity like gallons of gasoline in a tank. Yet, Hank had treated persistence as a scientist might an experiment. He committed in advance to more persistence as a test.

This way of thinking is unusual for freelancers. We’ll try new things from time to time, this offer or that marketing tactic. However, we keep the emotion in rather than taking a dispassionate, experimental approach. When rejection comes or when we don’t quickly get the results we want, discouragement overpowers resolve. We back of any commitment and stop doing the thing.

I’ve had dozens of conversations with freelancers, consultants, and agency owners who made fatalistic pronouncements about proven strategies: “Yeah, cold email outreach just doesn’t work for me.”

But was fate the problem? It just wasn’t meant to be? Or did discouragement beat down resolve while consistency hurried away? Sometimes, we give up too soon.

It’s worth noting that Hank didn’t. The Youtuber who was on the receiving end of Hank’s persistence eventually hired him.

The second line in the list above may at first seem unremarkable. Referrals happen all the time. Even so, Hank’s friend had enough confidence in his abilities to recommend him to someone else. We could say that’s what friends are for, but most of us don’t willingly risk our reputations even for friends. We send referrals when we trust the other person to not make us look bad.

Finally, Hank’s Google searches required a combination of self-awareness (”Here’s what interests me”), creativity (”Here’s something I can try”), and elbow grease (”Here’s what I need to do”). The result was an outreach strategy most freelancers haven’t tried.

So was Hank simply “lucky”? After he used that world, I pointed out several of the qualities he had displayed, including persistence, trustworthiness, and creativity.

When one Ann meets another Ann, is it luck?

Ann Miura-Ko is a venture capitalist and co-founding partner at Floodgate, and when she was a junior at Yale, she had the opportunity to work in the office of the Dean of Engineering as a student assistant. In an interview Ann shared how that low-profile job with its menial tasks led to one of the most important invitations of her life.

Here’s the abbreviated version of the story:

• As she was leaving to go to her first day of work, Ann called her parents. Her dad told her, “Make sure you do a world-class job.” She responded with youthful skepticism: “I’m photocopying and filing. There’s no such thing as world-class there.” Undeterred, he said, “Well, I’d still think about it.”
• Ann remembers later standing in front of a photocopy machine with a stack of papers, thinking, “What is world-class in this situation?” From photocopies to printing labels to getting doughnuts, she really tried to do everything as well as she possibly could.
• One day, the Dean’s executive assistant Sarah was out, and when he poked his head out of his office. he saw Ann. “Who are you?” he asked. Ann replied, “I’m Ann Miura. I’m your student assistant in this office.” He said, “Oh, I’ve heard of you. I need you to go and give this friend of mine a tour of the engineering facilities. I know you’ll do a good job. Sarah has told me you’re great.”
• The Dean’s friend turned out to be Lew Platt, then CEO of HP. Platt and Ann hit it off, in part because they were both from Palo Alto. Lew invited Ann to come shadow him during her spring break, and she accepted the invitation.

Ann’s week with Lew Platt changed her life:

“And I came back from that with my mind completely blown. I met Ann Livermore who was an executive and I’ve never seen a female executive in my entire life. And here’s someone who I can look at and see and I can see that people around her respect her. It was just a life-changing moment and it comes from that first comment from Dean Bromley who said, ‘I’ve heard of you. I heard you do a great job.’ And that’s why the opportunities opened up.”

Was Miura-Ko “lucky”?

Like Hank, she displayed several key qualities. She took her dad’s advice to heart, meaning that she was coachable. She pursued excellence in small things, and she did that so consistently that Sarah noticed and sang her praises to the Dean.

With both Hank and Ann, consistency preceded opportunity.

Four Kinds of Luck

In a series of conversations, Babak Nivi and Naval Ravikant, who founded AngelList and Venture Hacks, discuss four kinds of luck. They draw from a post by Marc Andreesen, who in turn drew from Dr. James Austin’s book called Chase, Chance, and Creativity.

For brevity’s sake I’ve paraphrased:

1. Blind luck. Something out of your control happens, and you chalk it up to “fortune” or “fate.”
2. Generated luck. Through hustling and doing lots of things, you generate opportunities. You put yourself out there, and luck “finds” you as a result.
3. Luck from preparation. As you accumulate skill, knowledge, and experience in a particular domain or market, you gain sensitivity to opportunities as they emerge. That is, you get lucky breaks because you noticed them when others didn’t.
4. Luck from character. As your character, mindset, or even brand becomes unusual and unique, you improve your position. Because you’re well positioned, opportunities come to you. Luck finds you.

Naval calls luck from character “the weirdest, hardest kind” and shares a memorable example: ****

“Let’s say that you’re the best person in the world at deep sea underwater diving. You’re known to take on deep sea underwater dives that nobody else will even attempt to dare. Then, by sheer luck, somebody finds a sunken treasure ship off the coast. They can’t get it. Well, their luck just became your luck, because they’re going to come to you to get that treasure. You’re going to get paid for it. Now, that’s an extreme example. The person who got lucky by finding the treasure chest, that was blind luck. But them coming to you and asking you to extract it and having to give you half, that’s not luck. You created your own luck. You put yourself in a position to be able to capitalize on that luck. Or to attract that luck when nobody else has created that opportunity for themselves.”

At a certain point, Naval says, luck becomes destiny:

“I think also at that point, it starts becoming so deterministic that it stops being luck. So, the definition starts fading from luck to more destiny. So, I would characterize that fourth one as you build your character in a certain way and then your character becomes your destiny.”

In an interview entrepreneur and former competitive cyclist Rob Fraser used slightly different language: “engineered serendipity.”

What then should we do?

We have no control over where we’re born, who our parents are, our genes, or a host of other facts and factors that plants us in a particular time in a particular place.

However, giving too much credence to blind luck is a mediocre strategy. Just ask the millions of people who never win the lottery.

Some facts and factors act like a sliding scale of difficulty. Hank lives in the United States. His geographic location makes it easier to get freelance writing projects. Ann Miura-Ko got into Yale, a prestigious school by anyone’s standards, and Yale made it easier for her to meet industry giants like Lew Platt. If you were trying to raise money for a startup, living in Silicon Valley might help. Serendipity is easier some places.

Even the folks who win the lotteries of birth or education still have to exert effort. Some will have certain advantages and try really hard at things they want to succeed at and still fail. Effort correlates with success, but it doesn’t cause it.

So, on one side of the expanse of human experience and appetite we see a boundary with a sign, No Control. And opposite it, we see another boundary with a sign, Effort That Ends in Failure. Where does that leave those of us who aren’t satisfied? What can we control and how should we think about the grassy field between the two?

We can expand the field, as well as the variety and richness of the opportunities, through effort, preparation, and character. All my reading, thinking, and living has led me to believe that.

When you encounter lack in your life, see if one of those three is missing: effort, preparation, and character. If one isn’t, you may simply need patience.

When you’re ready, here are ways I can help you:

1. Free Money. A pricing and money mindset guide for freelance creatives. If you’re unsure about your freelance pricing, this is the book for you.
2. Morning Marketing Habit. This course will help you build an “always be marketing” practice, become less dependent on referrals, and proactively build the business you want with the clients you want. My own morning marketing habit has enabled me to consistently make  6 figures as a freelancer.
3. Custom Business Roadmap. Gain clarity, confidence, and momentum in your freelance or consulting business.
4. Business Redesign. Raise your effective hourly rate, delegate with confidence, and free up 40 hours a month.
5. Clarity Session. It’s hard to read the label when you’re inside the bottle. I've done well over 100 of these 1:1 sessions with founders, solopreneurs, and freelancers who wanted guidance, a second opinion, or help creating a plan.