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Most people don’t think much about job transitions—until they’re in one.
Over the years, I’ve had a front-row seat to how people find and land jobs. Not as a full-time recruiter, but through the many roles I’ve played at the intersection of hiring, talent, and career strategy.
When I worked on the marketing team at Stack Overflow, I spent most of my time amplifying and promoting their now-defunct job board for software developers. As a result, I spent a lot of time talking with tech companies about how to work environments to attract developers, and talking with developers about the things that matter the most to them when looking for work.
At Union Square Ventures, I had the fun opportunity to serve as another type of talent node–people from all levels of a company’s hierarchy would reach out to explore their next career moves. As a result, I spent a lot of time refining my internal filter on what "good" looks like in many different roles and job functions. also started to recognize distinct patterns in how people navigate career transitions.
Here are some things I've noticed about people in transition:
Exploration: Even the most senior professionals tend to start their job searches broadly before narrowing their focus.
Iteration: There’s a natural period of iteration where job seekers refine their interests, testing ideas against the realities of the job market.
The Pause: Many senior leaders in tech need an "in-between" phase—something to bridge the gap between a high-stakes, high-stress role and whatever comes next.
Of course, not everyone follows this exact path, but it’s a common cycle.
By the way, this "pause" mode or "in between" phase of work is often when people try their hand at fractional work, gig work, or consulting. This driver of work change was so powerful it's what drove the initial conceptualization of Bolster to anchor on building a marketplace comprised almost exclusively of fractional work executives in transition.
But what about the rest of us? What do you do if you know you want out, but you just don't know where to start?
Lately, I’ve noticed a growing cognitive dissonance among my peers. More people than ever in my network are dissatisfied with their current work setup—but they’re also terrified to leave.
The job market feels unpredictable. It’s unclear who’s actually hiring. And in this AI-fueled era, even the skills required for the next wave of jobs seem up for debate. As a result, people are staying put. Which means they are staying frustrated. And feeling "stuck" for much longer than they used to. Not great.
In December, Harvard Business Review published an excellent analysis of the four reasons people quit. At the time, I wrote this reflection on why people quit, which includes a few tips for people to conceptualize their own so-called "work quests."
But all of that advice assumes you’ve already made the decision to leave. It doesn’t do much for the thousands of people stuck in dead-end jobs or wedged into roles that no longer support their growth. So how do you move from that nagging “I want out” feeling to actually building the courage to make the leap?
Here are a few ways I've seen people actually quit.
A few patterns I've noticed that gets people to actually make a change:
Tie your quitting to a significant company event. Lots of people leave jobs immediately after big events like exits, IPOs, or leadership changes. It's well-known in HR that after any downsizing event, there will be another 5-10% of employees who leave voluntarily. If you're looking for an excuse to quit, maybe you'll feel more comfortable tacking that news onto some other bigger corporate pressure, even one in which you have no control over.
Turn a personal or familial lifestyle change into a catalyzing event. Clearly this one has worked for me. As I'm 0 for 2 in coming back to my day jobs in both cases after I've had a baby. Like it or not, for me, the culmination point of something as significant as a new baby (compounded with all of the workplace finality required to tie up loose ends before going on maternity leave) has made it feel like a much easier time to lean into the change momentum. Whether you're having a baby, considering a move to the suburbs, moving home to be closer to your parents, or supporting your partner in their own career shift, these are potentially all natural change moments for you, too.
Force your own hand. Look, sometimes you just need to feel a little heat. One way that I've forced myself to keep moving in and out of different jobs as a fractional worker has been to intentionally scope fixed-window contracts, rather than long-term ongoing roles. That means I always have a hard stop—no guaranteed paycheck, no built-in safety net—forcing me to find the next opportunity. Unfortunately for me, I've found that cutting off a resource (i.e., money) can be an incredibly powerful motivator. If you can't seem to generate your own momentum in any other way, see what happens when you set (and articulate) a firm deadline out loud.
A career has both potential and kinetic energy.
If you’ve been feeling stuck in a job for a while, you’re sitting on a lot of potential energy, but not much kinetic energy to propel yourself into a significant shift. If you still want to make a change, you may need to latch onto the momentum of an external force already in motion—to ride the kinetic energy of something bigger than yourself.
For me, after four years as a fractional worker, I've been fully immersed in generating my own kinetic energy. Constant change and career agility have become second nature—it’s momentum I carry with me effortlessly. In fact, people have even told me that simply being around me makes them want to quit their day jobs too.
So if that's the vibe you're looking for right now, come talk to me, I guess.
I have a lot of friends who fantasize about quitting their day job but don't know exactly how to get up the guts to pull the ripcord. My guess is that this doesn't apply to many of us on Warpcast, as we're all doing our own weird vibes thing... but just in case you've got friends who need a push, maybe this blog post will help: https://hardmodefirst.xyz/how-to-[actually]-quit-your-job