Taking chances on people

Issue 209: Stories and expectations on the giving and receiving end

"I need someone to take a chance on me," is a phrase I hear a lot. Who can blame them? It's a brutal job market right now and people are hoping for an opportunity to show what they can do. I know well because it happened to me in the first recession in the 2000s.

Taking a chance on a person is making a bet not on what they are now, but the potential of what they can become. This requires a lot conviction and chance. NFL Hall of Famer Tom Brady was drafted in the 6th Round (the second to last round) in 2000 and then ended his career winning seven Super Bowl championships. This post shares lived experiences of receiving end and giving end of a chance. I’ll start by sharing the first chance I received.

My first chance from a future mentor

I matriculated from college a few years ago and no longer pursuing my Master of Fine Arts. Software became really interesting to me when I said goodbye to my Motorola RAZR phone for a phone strangely made by Apple—the iPhone. After getting hundreds of immediate rejections for design opportunities, I got connected with a few external recruiting firms since. Clearly, my portfolio wasn't working so reached out to a few talent agencies that offered freelance work. Of the dozens I reached out to, only one got back to me—a small but mighty boutique firm in Pioneer Square. They had a small project that needed to be done in 2-3 days. I took the opportunity. I was introduced to a woman who ran an independent UX studio, the person who needed work on the project.

We met at the Top Pot Donuts in Downtown Seattle. She briefed me on the project; visual explorations for a wellness iPad app—a new device launched. I was ecstatic to work on such a new innovation and didn't want to screw it up. Though the scope of work was a few billable hours, I spend triple that time un-billed because I wanted to get an opportunity. This was pre-Slack and video calls so I'd send designs back and forth over email. She'd give me feedback and I continued iterating. The designs were not immaculate and I'm sure she had to put the fit and finish to it. However, she thanked me for taking something from 0-to-85%, which freed up a lot of her time.

Working on that project gave me the confidence that I had a chance to pivot to software. We stayed in touch and there were several more projects. Throughout my career, I've ended up working with her at the agency and also full-time in-house. I often ponder what would be if I didn't get that chance. I'm sure eventually I would have made the switch, but her mentorship and willingness to make a bet on an unproven person like me accelerated and amplified everything.

Reflection: When someone bets on you

Make the most of the opportunity
Taking a chance on someone does not guarantee success.If the opportunity does not pan out, remember you don’t have full control of the outcomes. What do you have control of is maximizing opportunities any time you receive them. The people I take chances on have such rigor, hustle, and ambition that it compels you to believe there is no way this person would be unsuccessful.

Remind them of their impact
Every year, I send an email to my career advisors. I give them an update of what I’ve been up to professionally and personally. At the end, I remind them of the impact they made on me to say thank you. Many career enablers do not think much of their generosity, so to hear the impact it had may be new to them. In addition to making the most of the chance you got, let people know the impact it had on you.

Pay it forward
The number one way to return the favor to someone who took a chance on you is to pay it forward to someone else. If you’ve benefitted by someone opening the door for you in your professional craft, it’s your duty to return the favor for those in the future—the best way to invest in the ecosystem.

Taking a chance with a designer

Years later, I was now the person in a privileged position to take chances on people. Through the deep mentorship I received, I co-founded a product studio with a good friend, and had a lot of chances to pay it forward. There was a barista at the local coffee shop I’d go to who studied graphic design. I hired her to work with us on illustrations and visual directions on UI. There was also the UW grad working at the Apple Store who I referred to an Art Director friend who needed help at his digital agency in Downtown Seattle. Taking chances with your own company and resources is one thing. I quickly learned that when it’s making bets working in-house at a company, there were a lot of implications to consider. I’ll share a story of when we made a bet in-house.

At a previous company, our team was growing but enduring major growing pains from hyper-growth. That type of environment can be a buzzsaw for early career designers. I held a strong point of view about only hiring senior designers who have lived the pain of that experience. However, one of our managers had a promising early career designer they were advocating for. Our headcount was slim, so each hire had to count. I pulled our design leadership group aside to discuss, and they all committed to investing in this designer's growth. The designer had such an impressive growth mindset and desire to hone in on their craft. We extending an offer and this designer is continuing to thrive.

Taking this chance changed my perspective: excellence at all levels—the best principal designer to the best new grad/intern. This chance panned out because the leaders were all in on creating the right environment.

Reflection: When taking chances on someone

Foster the environment for success
Putting someone in a poor environment can ruin their professional career forever. I've known designers who quit the profession because though they got a chance, the environments were so toxic it turned them away from the craft forever. You’re responsible for the environment they are in.

Be mindful of excessive empathy
The primary reason designers are great at their work is their empathy in a human-centered way. However, it's important to contextualize the empathy as you make decisions. I've been the manager who wanted to say "Strong Yes" to every applicant because the desire to see everyone succeed, but that's not your job. It's important to remain empathetic while evaluating the best decision you can make. I remember applying for a Product Design Manager role years ago at one of the most iconic startups. The rejection letter was so kind, yet rigorous, that it taught me you can have a high bar while caring for people.

Your credibility is the currency for bets
When you take a chance, it is your credibility that's on the line. I once made an intro to a friend who was looking for a freelance designer. After a week of the intro, the designer never communicated with my friend and completely ghosted them. Though things are fine with my friend and I, that miss took a hit on how he viewed my referrals for a while. If you continue to send bad referrals to people, they will stop trusting your ability to evaluate people. It's important to take chances on people, but be realistic about the standards.

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Recap

History is built on incredible stories of humans rising to the occasion because someone believed in them. It's important to take chances on people, but not all of them will be Tom Brady. For every GOAT there are hundreds more who don't pan out. Take opportunities seriously when people give you one—give it your all. If you're in a fortunate position to take a chance on someone, be mindful of how you approach it.

There will be people you take a chance on who don't pan out along with people you pass who ended up proving you wrong. It's not about being 100% right. What's important is everyone continuing to place bets on people. I know I will.

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Hyperlinks + notes

A collection of references for this post, updates, and weekly reads.

• 221. Using AI for School is NOT Cheating by Steven Sinofsky

• Exceptional People Think in Decades by Dr. Julie Gurner

• Here’s What You Can Really Expect When Pitching Your Seed-Stage Startup at a VC Partner Meeting by Liz Wessel

• Soulcraft, Snails, and Synchronicity by Steve Schlafman

• Artificial intelligence is losing hype