The Biggest Career Decision of My Life Isn’t About Money

Aaron Orendorff
Aaron Orendorff

How do you make career decisions?

Not the little ones. The big, looming, “This choice will shape everything I do for the next few years and impact the rest of my working life” kind of career decisions.

It’s tough. In fact, you don’t even have to be staring down that barrel yourself for it to be a front-line issue. If you’re a leader, somebody on your team is facing the question right now. How do you navigate those waters with them? How do you acquire, develop, and retain talent?

For both groups, the temptation is to go after the money. We live — to paraphrase the great philosopher Madonna — in a material world and I am a material boy.

Your biggest career decisions can’t be about the money. There’s something better.

As natural as that feels … it’s the wrong path.

Three months ago, I walked away from my full-time job as a college instructor, away from a guaranteed paycheck, an employer-matching 401k, and union-won health insurance. It wasn’t as scary as you might think. I’d built up a freelance side hustle with monthly recurring revenue four to five times my living expenses. The decision that was long overdue.

Here’s the twist. That’s not the decision I’m talking about.

What I’m talking about went down two days ago.

As of February 22nd, I’m an official Content Marketer for Shopify Plus, one of the fastest growing ecommerce companies in the world. The agreement included the biggest cumulative payoff I’ve ever signed my name to.

The funny thing is … that payoff does not add up to the MRR I’ve been making as a solo freelancer.

So what’s the deal? Why would I choose to so willingly violate a core tenet of capitalism? What does my career decision have to do with decision-making in general? And why does it hold the single greatest lesson I’ve even learned about leadership?

In a word: love.

Love at First Tweet

It all started last year with a single, automated Tweet:

Back in early 2016, I was experimenting with Sujan Patel’s now defunct on a handful of my old guest posts. What Notifier used to do was grab every name and mention from a post and create Tweets which it’d send out to each person individually.

I didn’t know Tommy Walker — the editor-in-chief of Shopify Plus’ growing, enterprise blog — and wasn’t even trying to get his attention. To my surprise, Tommy wrote back.

You never know where the smallest gesture will lead yo

Always on the hunt for new business, those Tweets quickly turned into DMs. DMs into emails. Emails into a Skype chat, and then a freelance blog contract that suddenly made up roughly 25-30 percent of my MRR.

What’s more, the content machine Tommy was building was truly a thing of beauty. Three Trello boards linked together with a structured editorial process and detailed calendar all run through Google Docs, Slack, and weekly standups. Plus, it was accompanied by a manifesto entitled “The Code” that included lines like:

Opinions Are Bullshit. Do The Research.

“We solve real problems. We lead and create change in the world of commerce. If someone isn’t trying to emulate your work, you’re doing something wrong.”

All told, a pretty healthy payoff for one automated Tweet. Little did I know it was nothing compared to what developed next.

Love on the Job

To put it mildly, writing for Shopify Plus has been the single greatest working relationship of my life.

Tommy is an editor who actually edits … critically, insightfully, and with both wit and warmth. The stretch on that front has made me a better writer. (Hint: if you’re an editor, writers crave this. Give it to them.)

They also invested in my development outside of Shopify’s content itself. Tommy, for instance, exposed me to storytelling on the cinematic scale through Robert McKee’s Story: Style, Structure, Substance, and the Principles of Screenwriting — a 500-page tome that I devoured — and by enrolling the whole team in Aaron Sorkin’s Masterclass on Screenwriting.

Whenever I needed a contact, the dude was happy to help, even if it wasn’t for Shopify. Whenever I had a big win, he celebrated with me. And when I accidentally wandered into my first ambush on social media and then had my column at Inc. Magazine canceled, he talked me through each situation.

On top of that, they’ve been patient with me as a relative newcomer to ecommerce. Case in point, earlier this month I wrote a 2,000-word article on personas to which Tommy affixed this comment:

A very important distinction of what you’re talking about in this piece.

These are not “personas”; these are segments.

That doesn’t diminish the quality of the piece by any stretch; however, I think it does reposition it slightly from the outset.

Understatement? Absolutely.

I’d written an entire piece — a piece that I’d been assigned, mind you — about personas … that wasn’t actually about personas. We chatted. I adjusted. And that post eventually turned into a three-part series, about (shocker) segments.

The kindness, willingness to pour in time, editorial eye, focus on precision, and support culminated when we met for the first time in person at Shopify Plus’ Fashion Report launch party in New York.

Special thanks to Megan Walker for capturing the budding bromance

It’d be easy to take that little narrative and run right into how everything came together in this week’s big decision.

Before we do that, I don’t want you to miss the lessons on leadership.

Why? Because the loyalty and productivity Shopify Plus’ care led to — and there are far more examples I could mention — is not an aberration.

Love and Leadership

When Stanford business professors James Baron and Michael Hannan concluded their eight-year study of over 200 tech startups — Organizational Blueprints for Success in High-Tech Start-Ups — they arrived at one overarching conclusion.

In an attempt to determine the most successful managerial styles, the duo created five cultural models. To quote the MIT Sloan Review:

  1. The engineering model describes companies that attract employees by offering challenging work, that emphasize informal peer-group control, and that hire people for specific skills.
  2. The star model refers to companies that expect employees to internalize a strong professional commitment to excellence and require relatively little control. In this model, employees are selected according to their long-term potential.
  3. The commitment model depicts companies in which strong emotional bonds are the basis of employee attachment. Commitment-model companies believe in informal peer-group control and emphasize cultural fit in hiring.
  4. The bureaucracy model covers organizations with formal control procedures that attract staff with challenging work and focus on specific skills in selecting employees.
  5. The autocracy model references the organizations that motivate employees primarily with financial rewards. Such companies emphasize the importance of close personal oversight for control and coordination — and also make hiring decisions based on specific skills.

After the data came in, Baron and Hannan discovered the “commitment” model beat its counterparts on literally all fronts.

Even more staggering, as Baron told Charles Duhigg in Smarter Faster Better:

“Not one of the commitment firms we studied failed. None of them, which is amazing in its own right. But they were also the fastest companies to go public, had the highest profitability ratios, and tended to be leaner, with fewer middle managers, because when you choose employees slowly, you have time to find people who excel at self-direction.”

In similar fashion, the first chapter of Dan Ariely’s new book Payoff: The Hidden Logic That Shapes Our Motivations In Life opens with a quote from Viktor E. Frankl:

Life is never made unbearable by circumstances, but only by lack of meaning and purpose.

What follows is case study after experiment reinforcing everything I just shared: money doesn’t motivate … meaning, purpose, autonomy, ownership, personal growth, and encouragement do.

Payoff culminates with another quote from Frankl:

“For the first time in my life I saw the truth as it is set into song by so many poets, proclaimed as the final wisdom by so many thinkers. The truth— that Love, Meaning and Connection are the ultimate and highest goals to which man can aspire.

Then I grasped the meaning of the greatest secret that human poetry and human thought and belief have to impart: The salvation of man is through love and in love.

Those are heavy words for a book on motivation in the mostly professional sphere. But as Ariely concludes:

“Ultimately, this book asks you— whether you’re an executive, a parent, a salesperson, a teacher, a government official, or anyone else who seeks to motivate yourself or others— to think deeply and broadly about the effects of your approach.

If we do it right, the journey will reveal the secrets of more productivity, love, and meaning. Now, that’s motivating.

Other examples could be cited — like Intel’s discovery that a simple compliment increased productivity more than a cash bonus or Fidelity’s 2016 finding that 58 percent of millennials prefer “improved quality of work life” over financial benefits.

Still, it takes more than personal experience, objective evidence, and the words of great writers to teach us. At least it does for me.

Love Breaks Through

Eight months into my time on the freelance team, Tommy approached me with a question, “What would you think about coming on officially?” That was over the Thanksgiving holiday. I’d already resigned from the college and was wrapping up my final term.

Naturally, the first questions that came to mind were: “Can they afford me? What’s the price tag?”

You see, Shopify Plus was not my highest paying client … especially on the wage-per-post front. Nonetheless, it’d take a few months to hammer out a deal, so I said I was interested.

Two months went by and to my delight, Shopify Plus hired Hana Abaza — previously the VP of Marketing at Uberflip — as the new Head of Marketing. I knew Hana from a few Slack groups and we both spoke at Unbounce’s 2016 Conference. Even better, our presentations were glowingly written up in Unbounce’s Move Fast, Break Things and Get Rejected: Day 2 of the Call to Action Conference.

After Hana went on board … things moved fast.

Shopify scheduled what they call a “Life Story” interview and I laid everything on the table. Some of you have heard bits of my story, and (thankfully) the nitty-gritty, ugly details of what led me into online marketing four years ago didn’t scare Shopify away.

If you’re reading this Katherine Ste Marie, you are freakin’ amazing at your job. No joke!

Next was the one-on-one with Hana.

Proudly, I held my own against her genuine marketing genius for about 90 percent of the conversation. When she asked, “If you could wave a magic wand over Shopify Plus, what would you have us do?” I said a few wonderful things but realized after we hung up that I didn’t say the two things I should have: (1) analytics and (2) personas.

Also, I got schooled when, after I talked a little about all the popular content I’d created, she dropped this knowledge bomb:

At the end of our conversation, we broached compensation. I won’t go into detail here, but I’ve already hinted at my conundrum: I knew they weren’t going to match my MRR. So I threw out a number in between.

A week later, the initial offer came and after one more back and forth, the final package.

Love and the Biggest Career Decision My of Life

Given my strong relationship with Tommy, I reached out to talk with him. That might sound odd, but it just shows how far your track record as a leader extends in these hinge moments.

Here’s what he said via Slack:

“It is the company’s goal to make sure you get to do your life’s work.

“You are in a very similar position that I was when I started here, in that you can go anywhere. You do not need this job. You are a highly sought after talent, and any place who brings you on would benefit immensely from having you.

“For me, this has been the most difficult, challenging, and rewarding experiences of my career, and some of the things that have happened I never dreamed would have been possible.

“We met face to face at one such moment. I think you’re amazing and I would be be honored and lucky to have you on my team, but you could literally go anywhere you wanted with the skill and network you’ve built for yourself. I remember having that realization about myself when I was fielding offers, and it was such a moment of freedom.

The question you have to ask yourself right now, really, and I’m saying this as a friend, not as a potential employer, whose company do you want to build and what impact do you want to have on the world?

I don’t share all that to make myself look good; though, honestly, my pride isn’t above looking good as a side benefit. No, the reason I share that is this …

First, if you’re a leader, steal it. Don’t copy-and-paste, of course, but lean hard into the ethos behind those words. They are transformative.

Second, I’m slow and maybe you are too. It took a full hour before his last line sunk in: “The question you have to ask is … what impact do you want to have on the world?”

It’s cliché to talk about things like, “Do what you love and the money will follow.” It’s even more cliché to say, “Money doesn’t matter.”

But for the first time in my life, those clichés clicked. They hit my soul like a freight train:
I don’t need to make this decision based on money.

In fact, I shouldn’t.

That’s not the point. That’s not how I’m going to pursue lasting happiness. That’s not how I’m going to do great work. That’s not the ingredient of mind-blowing professional relationships. ‘Can they afford me?’ and, ‘What’s the price tag?’ are the wrong questions.

Sure, I had to ask those questions a couple years ago. But I don’t anymore.

What do I really want to do?

Oddly enough, this epiphany didn’t come out of the blue, even though — in the moment — it felt like it.

A few months ago, after leaving the college job, I started work with a coach, Candace Horton.

One of the exercises was to put together a list of my current clients, the workload for each, and the monetary payoffs. As a little bonus, I created another column on my spreadsheet marked “Happiness” and I scored each client on a scale of 1-10.

Besides revealing one project I needed to let go of, I didn’t go back to that spreadsheet until the final offer came through. In the airport on Tuesday, I pulled it up, added in all the new numbers (the things I thought were guiding lights) and noticed the last column: “Happiness.”

On it were one 5, three 8s, two 9s, and a single 9.5 — Shopify Plus.

There it was. The final, happy-measured, breakthrough straw brimming with all the sexy gusto a simple numerical rating can muster.

After one last conversation with my lovely wife, I sent an email outlining my thought process that ended with: “Let’s do this.”

Love and Your (Professional) Life

Will I make less money this year because of my career decision? Probably.

At first, that sounds stupid, borderline sacrilegious.

The pressure to get bigger, to scale, to open an agency, to make something that makes serious money is enormous. All the cool kids are doing it.

But is all that the real reason we do what we do? Maybe launching your own agency or product is the dream. And yet, even in that setting, is money the be-all-and-end-all metric of human decision-making? Is the “price tag” how we want to shape our lives and lives of the people around us?


At least, I’m trying real hard to live like it’s not that way for me.

My hope is … that’s also not the way for you. Whether you’re staring down the barrel of a big career decision or trying to help someone you care about make their own, there has to be something more.

And there is.

How we treat ourselves and other people, especially the people we lead, how we make the really big decisions should ultimately come down to one thing: love.

So let me ask … what’s guiding you?

Let’s save the world from bad content

Close Icon
Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.