Buying my time back through career gapsFeatured

You probably remember people saying “Just take the first job out of college, so you gain some experience.”

I heard that too, but I also heard something else: “There’s an opportunity cost to taking a job one doesn’t find enjoyable.”

The argument is that you might get “guaranteed” pay at a steady job, say for a year, but what could you be doing instead that grows your career/finances by 2X or more in the same amount of time? I took the latter advice and it grew my base salary by more than 2X with my first job in tech.

My first gap: waiting for the right opportunity

Back in 2016, I was graduating with a Computer Systems Engineering B.S. degree, with no software engineering internship experience, but I did have a full time offer from Boeing’s Info Tech Sector for $60K/year in St. Louis. That’s even after interning for two summers for Boeing. While I tried to negotiate with the recruiter and inquired about positions in the Engineering Sector, the role and offer remained the same. I would have to relocate to St. Louis, a city that doesn’t have job growth opportunities I was interested in, and for a company that didn’t want to help me pursue my chosen career path.

To me, it was an obvious opportunity cost if I were to take that job and was the first time I bought my own time back by taking a gap year. So with no other job offer on hand, two weeks after college graduation, I moved to San Francisco with the $20k in savings from my past internships. For the next year, I spent the majority of my time thinking through which field I wanted to pursue, attending meetups to network with people in tech, building Android apps, studying for software engineering interviews, applying for jobs, attending interviews and failing at them, picking up running as a stress reliever, working part time at Trader Joe’s with the 5 am shift, working through a failing romantic relationship, and watching my bank account drain to the point where Chase started charging me fees for not keeping a minimum balance, and from time to time, crying out of frustration and exhaustion.

Though often painful, all these experiences led to me creating things like a complex weather app, getting a lot better at interviews through valuable failure and practice, and demonstrating individualism gained through soul searching. With a friend’s referral, I landed my first tech job as an Android Developer Intern at a self-driving car company.

I went on to become the second Android Engineer and first female Mobile Engineer of the company. When I negotiated for my full time compensation, I received an offer with a base salary of $120k/yr and another $40k in other compensation. Though it was extremely difficult to live through the gap year, I made all the money back as if I took the $60k/yr offer and more. Remember that every future compensation offer after will hopefully build on top with increases of 10% - 25% from your previous salary, so don’t sell yourself short! Always politely and strategically negotiate!

It let me begin my career with an exciting self-driving car startup doing Android work. Perhaps even more importantly, I got to live in a city littered with tech opportunities and pick the brains of some of the brightest tech minds in the world. It also allowed me to attend local events, conferences, and meetups (found on sites like hosted by disruptive companies with a focus on recruitment, educational talks, and sometimes even with a bonus of providing experimental foods!

My second gap: recharging and reassessing to emotionally catch-up

Silicon Valley startups favor relentless work and breakneck pace, so when my time at the self-driving car company ended, I knew I needed to take another break to recharge and reassess. I had worked and learned so much, I knew I had to take time to myself to emotionally catch-up with what I’d lived. Soon after, I got into a skateboard accident which added some months on to the gap period. Living off of savings and unemployment insurance (remember that your taxes pay for it, so make sure to pay yourself back if you ever end up in that situation), I took the time to heal from a concussion, neck pain, and tailbone bruising.

I also knew there were some interesting questions to which I needed answers: What practices were good for software engineers? What were good Android engineer fundamentals? What were company-specific software, knowledge, or opinions rather than industry-wide? With which of those concepts, values, or execution methods did I agree? Was I happy striving to be that company’s top performer? Were the interview questions we asked candidates actually a good indication of their ability as an Android engineer? What am I going to look for in my next employer or role? Do I still want to be an Android engineer?

Taking the time to work through those questions helped me better plan my career and answer questions that came up in interviews. “Why did you decide to interview with us?” “What gets you excited about this role?” “Tell me about an exciting coding/behavior challenge you worked through.”

Those answers began to come easily and helped me stand out because my responses were derived from reflected core values and experiences. In addition to life pondering, my solo application was recognized as a top 10% applicant of the YC Summer 2019 batch. Soon, I landed at a dating app company, which satisfied my curiosity on how that industry worked behind the scenes.

My third gap: reflecting on who I want to be

When March 2020 happened, everyone’s lives turned upside down. Soon after, I took gap months for the third time. The world fell apart, and so did my mental health and soon my job too. I again asked a lot of the same questions listed above. This time, some answers were more structured and getting better at being applied across companies. But one question got a very deep and clear answer, “How do you pick the right employer for you?”

I gathered that there are a lot of incompetent “leaders,” questionable practices, and extremely tedious and biased interview processes out there. Some of the obvious bad fits were the ones that left you feeling terrible when you failed your interview or companies which featured poor collaboration, rude interactions, or poorly designed interviews. Accept what they show you and move on.

By now, you've gone through lots of company interviews and you have some offers, so ask yourself, “Did I like who I was when I was interviewing with that group of people?” The worst case is you didn’t like who you were even though you aced the interview by passing their test of “this type of person will succeed in our company culture and expectations” (you can still use that offer to counter other offers though!). Who will you become in a year if every day you become a little more like who they want you to be and a little less like who you want you to be?

Now, if you’ve found a company that’s happy to pay what you’re worth, is excited to hear about your gap time, shares your values, and they are a delight to be around, then you’ve found your group of people with which to grow your career 🎉.

For me, that was Nearside. I was the second android hire in the mobile team and the only female engineer at the company at the time of hire. Where unlimited PTO meant unlimited and they provided corporate-like benefits such as paid maternity leave and student loan payment matching, while maintaining respectful colleagues, work-life balance, competitive pay for startups, and building a banking system for the underserved. Thank you Nearside for exemplifying what it feels like to be valued and cared for as an employee on a daily basis. Nearside was later acquired in October 2022 and much of the business was wound down.

My fourth gap: in progress

During this period, I’m taking my time to write this Elpha post to you all. There’s always more money to be made, but you never get time back. To add some more reassurance, the employers who have recognized my value and skills have always been excited to hear about my gap adventures, and have given me at least a 10% compensation increase from my previous job.

What else might I be doing during this time? Experimenting with food in the kitchen is a form of therapy in my opinion. I’m also building the app that caught YC’s interest a few years ago. Working on my own project will also help with my software interviews in the future. Remember, you should only ever work for you 😉.

What should you do now?

It’s never too late to buy your time back, take time off, or take advantage of government programs (your taxes paid for them)! Be okay with just existing. Go buy yourself that travel, class, or food experience. Take the time to build your own brand or create transformational networks. Reconnect with someone you care for but never had the time to stay in touch with.

Remember to budget strategically and be realistic about your monthly expenses. When it comes time to find a job (or build your own business!) again, allow 2-3 months to land a job, so you aren’t forced to trade survival for opportunity cost. Be chatty about what you’ve learned during your gap time! You always come back stronger and more desirable because of it. Your confidence will beam from within and the right group of people will be fighting for a chance to get to work with you. Hopefully by then, you like yourself more than ever before and that’s the only validation you need to keep going. Know that I’m rooting for you 🙂.

Thanks for sharing your experience. I am experiencing a career break for the first time and I am *a bit anxious* to say the least. Iā€™m definitely Increasing my skills and learning new things where I can. I got accepted into a skills accelerator for my field, which starts next week! Glad to know Iā€™m not alone in this.
Thank YOU for sharing your experience with taking a career break. And it delights me to know you feel less stress because of this story. ā¤ļø This community looks forward to many more things you get to do šŸ’Ŗ.
Thank you so much for sharing your story. I resonated with this a lot and it's nice to know it is ok to take time off. I am on my first leave of absence (but I had to take it because I got sick from prolonged stress). I was terrified to ask to take that time off and even more terrified of what I would do with having so much time to myself, but I am so glad I did it. I have been able to heal and develop new skills and renewed purpose. Similarly, I am glad to know I am not alone and it is ok.
Thank YOU for sharing your current experience with taking a break! I'm am so glad you feel better now both physically and mentally! When your body and mind feel good day after day doing a thing. Is always the right signals that's the right path šŸ’Ŗ . I also like to add that I too gotten physically ill due to mental stress and was put on short term disability leave because one of the symptoms were I lost 11 lb in 10 days. I'm so glad you found this piece helpful, I'm so glad you're sharing your story. And WE can't wait to see what you get to do when you're ready šŸ˜Ž. See you around Tiffany šŸ™Œ
I resonate with this a LOT! I've taken many gaps in my career due to various forms of burnout, and last year I burned out so badly that I needed to take months to recover. I learned a ton about balance and living more sustainably, and was also able to set up a consultancy. I realized that I'm not quite ready to commit to working on my own (as a designer, I thrive on collaboration), I really miss being on a team, and I'm ready to join another company while bringing in everything I've learned so far.I hope your current break rewards you and teaches you something new!
Hey Carrie, Glad it resonated with you šŸ„³. And I'm so sorry to hear you had the similar struggles, and I'm glad you listened to your body and took time off! My current break has been very rewarding. I've been learning new coding skills and reading plenty! I think we all have those back stacks of "oh this looks so interesting, when I have time I'm going to try that." Is been really nice getting to go through that list!
Thank you so much for sharing this, Laurie!