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

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:

• Freedom
• Financial upside
• Learning

The most important priority was freedom. I’d spent most of my career working remotely (a decade pre-Covid), and was certain that there was no world in which I saw myself going into an office five days a week. Remote work allowed me to optimize my own productivity. I had recently had my second child and also had a three-year-old, and loved having control over where and how I did my work.

As long as I know what I need to accomplish at work to be successful, I can structure my day to benefit both my professional and personal life. I start each day having breakfast with my family, and then dive into deep, focused work—all before I have a single meeting. I end each day by taking my kids to the park. My team at Trello knew, as my current team knows now, that time is sacred, and that I'd get back to them within a requested time frame. I have always been ruthless about time management and optimizing my time at work to be fully present when I'm with my family. This control is a key factor to my productivity.

My time at Trello also gave me some financial freedom to bet on new and uncertain opportunities—and startups can be high-risk, high-reward.  After my experience at a big tech company, I craved the autonomy and control of guiding an early-stage startup. 

I also wanted to learn something new every single day. I have an old mantra:  “Do something that scares you every day.” For me, the scary stuff is educational, instructive, and what helps me grow the most. I wanted to learn exponentially, and to learn by doing. 

When I wanted to learn about investing, I worked with venture capital firms. When I wanted to learn about starting a business, I started one and learned a ton. The best way to learn is to put yourself in the position to get firsthand experience.

What are my options?

I knew I wanted to give myself time to explore. I’d spent my career working mostly in and around startups. This left me with a few natural options:

• Join a growth-stage company as a chief marketing officer or senior vice president of marketing (which I rejected for the reasons I discussed above)
• Transition to venture capital investing
• Advise startups on marketing strategy
• Start a company

My next steps involved trying these options in a low-risk way that would allow me to be sure before I made the leap.

How can I try things out in a low-risk way?

Did I want to be an investor? Or an advisor? The only way to find out was to try it. I became an advisor to a well-known venture fund, helping portfolio companies with go-to-market strategy; made lots of angel investments in early-stage companies, and took on an advisory role to a startup. 

I’ve always been keen to develop my professional network, so whenever I had the bandwidth to take on opportunities, I let people know. I posted on LinkedIn, asked my network who I should talk to, and reached out to people to chat over coffee. That’s how I was introduced to Denzil Eden, founder and CEO of Smarty, an AI-powered day planner. She was starting to think about a go-to-market strategy for her company, and I found that I loved helping her think through her business. 

It might seem like everything I was doing was systematic and logical, but this networking period wasn’t an exact science—I had to signal what I wanted to learn to the universe and that came with lots of trial and error. In turn, the universe delivered opportunities. My framework made it easier for me to decide where I wanted to spend my time. When it came time to make decisions, I thought about whether the opportunity fit the framework and how. For example, being an executive meant little freedom, some financial upside, and a lot of learning. But because the freedom was limited, it didn’t fit the framework.

After a few months of investing and advising, I realized that neither would be the next full-time career step for me. 

I found some aspects of investing not as interesting as others. Investors constantly need to cultivate deal flow: doing deals, meeting entrepreneurs, getting insights into market pricing, and having a niche—this part I enjoyed. Great investors also need to know the ins and outs of startup financing, deal structure, and cap tables. This part was less appealing. 

As an advisor, I would find that I was itching to execute on my own work after talking with founders. While there are people who advise full-time, they tend to either become a fractional executive or a consultant, neither of which sounded particularly interesting to me—I wanted an opportunity to go all in. 

The founder route

I had been a founder before and was interested in being a founder again, given the right co-founders and circumstances. Earlier in my career, I was the founder of a startup called Matchist. I sold it after business school and joined Trello. Before that, I was on the founding team of a startup that got acquired by Groupon. Having gone through the journey from beginning to acquisition more than once, I knew that being a founder life ticked all of my boxes: freedom, potential upside, and learning.

About six months into my exploration, a couple of my teammates from Trello also left and began to consider their next steps. Over many meetings and conversations, it was clear that we had similar feelings about the next phase of our careers. We had worked together for many years on Trello’s executive team. We still liked each other—against all odds—and were at similar life stages with kids and other responsibilities. We each had some financial flexibility and relevant experience from our time at Trello, and shared similar values and outlooks on life. We all value integrity, transparency, autonomy, being good human beings—oh, and building world-class products. Together, we were part of what made Trello so successful as a culture and a company, and we all had nostalgia for the early days. I proposed we team up and tackle another big problem.

While we weren’t your standard 22-year-old founders, we were experienced operators who had seen what it takes to build a successful company. We were hungry to replicate that experience, this time as founders.

A few months later, my former coworkers and I became co-founders. Every interaction with my co-founders enforced that this was the right next move. I was giddy after our meetings. Often, I couldn’t sleep because I was so inspired by our plans. For the first time in a while, I felt excited, terrified, and creatively motivated. 

I could tell that I had made the right choice.

Soon, Hoop was born. We’re building a smarter way to manage tasks at work and cut down on busywork. Imagine a to-do list that writes and manages itself, across all the tools you use like Zoom and Slack. Our goal is to make it so you have fewer distractions and waste less time, so that you can do what humans do best: concentrate and create. 

Trust the process

Hoop is currently in the product development stage. We started up 18 months ago and are a team of six. So far, it has been a journey. As a co-founder and CEO, I’m constantly learning, and I’m committed to growing an amazing company culture with a fantastic team and a clear mission. Every day, I grow more sure that this is the right path for me. 

Introspection costs more after you’ve made long-term commitments. Take your time and follow a process—following this framework took me about a year. Figure out your options, identify your current season of life, and try to understand what’s most important to you. Test things out in low-pressure ways and see how they make you feel. 

Ultimately, you only have one life to live. Make sure you’re following the path you’ve set out for yourself and not anyone else’s.

Stella Garber is the co-founder and CEO of Hoop. Previously, she led marketing at Trello, building the team as its initial marketing hire to Atlassian's acquisition and beyond. She is an angel investor in more than 30 early-stage tech companies.