Career Transitions: A Step-by-step Framework

If you’ve worked in tech for any period of time, you’re probably no stranger to making a job or career transition. I myself have undergone several: from magazines to book publishing, to an early-stage startup, to late-stage startups, and back to early stage at Every. With each shift, I asked myself some of the same questions that former Atlassian executive Stella Garber did when she was contemplating her next move. Stella has codified these questions into a framework that helped her take the leap to cofounding her own company. I hope you find it valuable wherever you are in your career path. —Kate

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The year was 2021, and I was at the top of my career.

Seven years earlier, I became Trello’s first marketing hire, spending the successive years building out the software company’s marketing team and strategy. I was hired as the first remote executive and helped build out a vibrant company culture with low attrition and great vibes. I held a seat on the executive team, where we oversaw hockey-stick growth in just a few years.

That growth naturally attracted outside interest and in 2017, Atlassian acquired Trello for $425 million. There were clear benefits and growing pains of this takeover, but what felt most different was that we were now part of a much larger firm—our team of about 100 had to integrate with a firm of 1,200. Just a few years later, the headcount has surpassed 10,000. 

But eventually, about four years after the acquisition, I started to feel like I was no longer learning or growing professionally at the velocity I desired. Even though I was proud of my accomplishments and position, I knew that my time there was nearing its end. After all, being a middle manager of a large software company was a very different job than the one I had originally signed up for, leading marketing at a small startup.

I knew my time was up—that was the easy part. The hard part was figuring out what came next. I wanted to be methodical about my next steps. By the end of this process, I realized I had developed a framework to help me understand what I wanted from the next stage of my career.

The framework asks five questions:

• What is my season in life?
• What is most important to me right now?
• What am I trying to optimize for?
• What are my options?
• How can I try things out in a low-risk way?

By going through and answering each of these five questions, I put real words to the problems with which I was struggling and, in the process, found one logical answer: I wanted to start a company. That company is called Hoop, where we are reimagining modern task management. My time co-founding Hoop has been everything I could have hoped for in my next step—but I don’t think I would have gotten to Hoop without this framework. 

I’ll dive into how I answered these questions and provide a guide for how to use my framework for your own transitional moment—whether it’s figuring out a new job, career path, or a big life change.

What is my season in life?

A mentor once shared a helpful way to think about opportunities in life: Life has seasons. There are seasons for buckling down and learning, like when you’re in college, and there are seasons dedicated to family life, like when you have your first child. Some seasons are for making risky bets, whether you’re investing in yourself or others, and other seasons are for taking jobs that feel safe because you need financial security.

In order to understand my season in life, I had to be introspective and take note of how different roles made me feel. In 2021, when I was looking to leave my job, recruiters were reaching out to me several times a day with juicy marketing roles at growth-stage companies. Looking at my résumé or LinkedIn profile, the obvious choice—or, at least, the expected career path—seemed to be to take on the next stage of leadership in tech. The brand names were exciting, the valuations were increasing every six months, and skilled recruiters could be convincing.

But something didn’t sit right with me about these opportunities. I interviewed with a handful of firms, even getting an offer from one pre-IPO company following nine interviews, including with founders and board members. But during each of those interviews, I found myself wrought with anxiety.

Did I really want to inherit the dysfunction and expectation of an already-established team? I particularly enjoyed building my own team at Trello. Did I want to jump into a fast-paced, high-stakes role after the intensity of my last experience? Did I want to control my destiny at work? Did I want to sit in Zoom meetings for eight hours every day and work in the mornings and evenings? Certainly not.

My season in life had changed—I wanted a job where I could set the direction, hire my own people, and build a culture that represented my values.

I had to remind myself that the choice I would make this year might not be the choice I would make next year—and that’s alright. Often, life transitions can feel stressful because choices feel so permanent. Reframing life into seasons helps take the pressure off of one particular choice, and reminds you to keep adapting and making the best choice for your present circumstance. 

What is most important for me right now?

Once I realized that I could let go of imagined expectations of my career, tons of possibilities opened up. Someone recommended the book Designing Your Life, written by two Stanford design school professors who bring design thinking into making life choices. 

That book taught me to pay attention to physical cues, like how my body reacted to different tasks, and audit my calendar to reflect on activities that excited me. At the end of each week, I made notes on how I was feeling. I found that I was energized from talking to people. But I also liked to disappear and focus on things like writing. What I knew, from the end of my time at Atlassian, was that the thing I hated most were soul-sapping, back-to-back meetings. I asked myself what was most important to me. Did I want to learn? Did I want to earn? Did I want both? What types of opportunities would appeal to me?

What are you optimizing for?

After a few weeks, I realized I wanted to optimize for three things: