Reader Q&A #1: Should You Take a Gap Year in Today’s Economy?
Occasionally I get a reader who reaches out using my contact form, which I always appreciate. It’s a nice reminder that I’m not just speaking into the void. Keep those emails coming.
This time, Sydney sent over some especially thoughtful questions. So much so that I thought it would be great to share as a post, in case any other wandering mind finds its way to my little corner of the internet.
Let’s get into it!
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✉️ The Questions
Hi Amanda! Thanks so much for writing about your gap year. Everything you said about your "why" resonates with me. I've been considering taking a gap year of some kind for several years, and I think I'm finally ready to take the leap.
I have a couple questions I'm interested in your opinion on:
Do you think there's a major risk in leaving a stable job in the current economy and political landscape, enough risk to not take the gap year? What would you say to the people who advise others to stay in the stable well-paying job and keep your career on track?
What was it like entering back into the job market, in terms of finding a job, interviewing, the competitiveness of the job market, etc.?
Hope to hear back from you!
Best,
Sydney
💭 My Answers
Hello Sydney!
First of all, omg! So exciting that you’re ready to take the leap. It’s definitely a scary decision, but also an extremely exciting one. I can tell you’ve already put a lot of care and thought into it.
It’s been about 3 years since I embarked on my gap year, and already 2 years since I’ve been back at work. Has it really been that long? Time seriously flies, I didn’t realize how much time had passed until I did the calculation just now.
All that to say, I’ve now gone through the full cycle: taking the leap, stepping away, and re-entering the job market, so I’ll do my best to share what that experience was actually like.
Q1: Is it too risky to leave a stable job right now?
On risk in today’s economy
This is such a good question, and honestly, a very fair one given the current economy and everything going on in the world. I think the honest answer is that yes, there is real risk. There’s always going to be some level of risk in leaving a stable, well-paying job without a clear next step lined up. That part doesn’t really change depending on timing.
So the more interesting question isn’t just “is this risky?” but rather, “what kind of risk am I choosing to take?”
Because on one hand, there’s the obvious, external risk: the job market, the economy, how long it might take to find something again. All very real, very practical concerns. But on the other hand, there’s a quieter, more internal kind of risk: the risk of feeling stuck, of burning out, or of wondering for years whether you should have just done the thing you’ve been thinking about for so long.
For me, that second category ended up weighing more heavily.
Is it enough risk to not take the gap year?
Now your question is whether the risk is enough to not take the gap year. Because the reality is, life is full of risk. There’s risk in leaving your job, but there’s also risk in staying. You just have to decide which one you’re more comfortable living with.
Before I quit, I spent a lot of time thinking through the practical side. I made sure I had enough financial runway, thought about what worst-case scenarios could look like, and asked myself whether I felt confident in my ability to re-enter the workforce later on. Once I had those answers, the decision started to feel less like a blind leap and more like a calculated one.
And then it became a different question altogether: Is this something I’ll regret not doing? For me, the answer was very clearly yes. (I’d recommend reading about Jeff Bezos’ regret minimization framework.)
What I’d say to “stay on track” advice
The “stay on track” advice is really rooted in optimizing for predictability. And that’s valid. But it’s not the only way to think about a career.
I read this piece a while back about how we tend to “maximize optionality,” meaning we try to keep as many doors open as possible. But over time, that can actually become a way of avoiding real decisions and delaying what you actually want.
One thing to remember is just how long careers actually are. Taking a year off feels like a huge deal in the moment, but in the context of a 40+ year career, it’s really just a small slice of time. If anything, taking a step off the default path, intentionally, can actually give you more clarity on what you want in the long run.
For me, I gained a lot of clarity on my relationship with work, how I think about ambition and success, and how it all fits into the kind of life I actually want.
Q2: What was it like going back into the job market?
What the timeline actually looked like
I entered back into the job market in April 2024, and it took me about ~3 months of serious job searching to land something I felt good about. That timeline actually ended up being pretty in line with a lot of my friends who were in similar situations at the time, many of whom were job searching due to layoffs, so I went in expecting it would probably take around 3–4 months to find the right role.
How I approached the job search
When I say “3 months of serious job searching,” I don’t mean I was literally applying to jobs 8 hours a day, 5 days a week. But I was very much prioritizing my time around it. That meant regularly applying to roles, reaching out to my network and letting people know I was actively looking, staying on top of recruiter emails, and being flexible with scheduling for recruiter screens and interviews.
Especially in this market, where it feels like there’s a new layoff announcement every other week, it’s important to stay on top of opportunities as they come. But at the same time, you also need to make sure you’re actually prepared for them when they do. For me, that looked like doing mock interviews, brushing up on how I told my story, and talking to friends and mentors about how to position myself well.
What the market felt like
Something I learned pretty quickly is that hiring managers can be quite picky right now (even more so than 2 years ago). They’re often looking for candidates with very direct, relevant experience so they can de-risk the hire. Plus, there are more qualified job seekers than available positions, which means they have the upper hand. So it’s super duper important to pitch yourself in a way that removes any guesswork on their end.
What does that actually look like? Even if you don’t have perfectly 1:1 experience, there are still ways to position yourself. Clearly map your past experience to what they’re looking for, explicitly explain why you’re a strong fit, and tell a cohesive story that makes your background feel intentional. Basically, make it as easy as possible for them to say yes.
At the same time, you also have to get comfortable with the fact that sometimes you’ll be passed over for candidates who do have more direct experience. That’s just the reality of the market right now. Your job is to take the experience you do have and sell it as best as you can, in a way that still feels authentic to you, but not take it personally if they find a closer match.
In some cases, this can actually lead to recruiters or hiring managers matching you with a different team or role within the company, or even reaching back out later when something more aligned opens up. Timing really is everything (which is why it’s important to take advantage of any in you do get!)
How the gap year came up
On the gap year specifically, this was something I was honestly a bit worried about beforehand. People would say things like, “What will your next employer think?” But in practice, it came up way less than I expected.
I didn’t actually have many recruiters or hiring managers question it directly. And when it did come up, it was never framed as a negative. It was more of a neutral or even curious question.
I think a big part of that comes down to how you talk about it. If you can clearly explain why you took the time off and what you got out of it, it comes across as a very intentional decision rather than something to be concerned about. And honestly, with the right people, it can even be a positive. I had a few moments where someone would say something like, “Oh that’s amazing, I did something similar,” or “I’ve always wanted to do that.” There’s a bit of a shared understanding there.
The emotional side of job searching
All that said, job searching is rough process. There’s a lot of rejection involved, and it’s hard not to take it personally at times. I had to constantly remind myself that it’s part of the process, especially in a more competitive market, and make sure I was also taking care of myself along the way. Having a strong support system, and accountability with friends going through the job search at the same time, helps a lot with the emotional roller coaster that is job searching. Make sure to book in time for breaks and still doing the activities that de-stress you and bring you joy 🙂
Overall, I’d say the re-entry was very doable. While I was able to market my background and skills from my past 6 years of working effectively, but it was definitely not easy, so it’s important to go in with that expectation. It mostly just came down to being intentional, staying on top of things, and giving myself enough time and space for it to play out.
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Thanks for sending in the questions, Sydney! And good luck with your leap. You got this!
Amanda
A lil snapshot from a recent sunset hike from last weekend
