Sometimes the Best Career Move Is Backwards

Why I took three pay cuts on purpose (and how each one unlocked my next big move)

We’re all raised with this idea that a career is a ladder. Every move has to be “up.” A better title, more money, a more prestigious company.

But the reality is, a modern career is more like a rock climbing wall.

Sometimes, the best path to the top requires you to move sideways, or even down a bit, to find a better handhold.

I’ve done this several times in my career, and each time, it was a deliberate choice that unlocked my next big move.

Let me walk you through a few examples.

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Case Study 1: The “Foot in the Door” Play

When I graduated with my Master’s in Mathematical Finance, my classmates were getting offers for these highly analytical, six-figure jobs.

But the catch was, none of them were in New York City, which was my ultimate goal.

I had an offer from The Royal Bank of Scotland, but it was for a middle-office, Trade Support role. It didn’t require much quantitative analysis. It was basically pushing buttons to move trades through systems. And the salary was probably the lowest in my entire graduating class (i.e., no where near six-figures).

But the job was in Connecticut, a train ride away from New York. I knew I just needed to get my foot in the door.

I took the job, and from day one, I started networking. I met people, I learned the business, and after just five months, I landed a new role internally with the Market Risk team.

This job was exactly up my alley. Highly quantitative, working alongside PhDs, analyzing risk for the options desk. And it came with a $30,000 salary bump.

That “bad” first job was the stepping stone that got me where I needed to be.

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Case Study 2: The “Profile Building” Play

A few years later, after my footwear brand didn’t go as planned, I knew I needed an MBA to repackage my story and build my leadership skills.

But in my research, I noticed that a lot of students at top business schools had “strategy” on their resumes. I didn’t.

I had opportunities to go back into finance after I stopped working on my little brand startup, even a temp role at Credit Suisse that paid well, but I knew it wouldn’t help my MBA goal.

So I made a choice. I turned down the six-figure finance jobs and started applying for only strategy roles, in any industry.

I eventually convinced a director at a hospital to hire me as a Strategy Analyst. It was a massive pay cut, but I was thrilled. I was learning, I was doing pure strategy work, and I was intentionally building the exact profile I needed for business school.

That intentional step back is what ultimately helped me get into Kellogg.

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Case Study 3: The “Clarity” Play

Even after my MBA, when I left consulting, I took another massive pay cut on my base salary to join the digital health startup.

Why? Because I knew the 70-hour work weeks in consulting were crushing me, and I needed to be in a place where I was happier.

That move paid off in an unexpected way. The better work-life balance gave me the time and mental space to reflect, to be more tactical, and to plan my next move without being burned out.

It was during that time that I built the plan that got me into the retail industry. The industry I always wanted to be in.

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It’s Never Too Late

So I want to leave you with this.

It is never too late to pursue your passions. Don’t let money, title, even age, or what other people think dictate your moves.

Your career journey may not be a straight line. It will have twists, turns, and moments that look like a step back.

But as long as you are being intentional, and as long as the long-term trend of your journey is moving forward and up, then you are doing the right thing.

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Your Task

Your task for this post is a mental one. Look at your North Star.

I want you to ask yourself: Is there a “stepping stone” role, maybe with a lower title or salary, that could actually get you there faster than trying to make one giant leap?

Just consider the possibility. It can open up a whole new set of opportunities.

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Now, as you heard in my story, one of my biggest intentional “step back” moves was taking that strategy job with the specific goal of getting into a top MBA program. That brings up a huge question that many people face in their careers: “Should I get an MBA? Is it worth it? And when is the right time to go?” In the next post, we’re going to dive deep into that exact topic.

I’ll see you there.

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Next up: Is an MBA worth it? (My controversial take)

Here is the complete career playbook (all 26 posts with real-world interview, resume, and career examples) for anyone who is pivoting roles, industries, about to graduate, stuck in their current path, not sure what to do next, etc.