6 min read

What to do when you’re not sure what’s next in your career

What to do when you’re not sure what’s next in your career
Photo by Tim Mossholder / Unsplash

I wrote this post sometime last year when a friend was asking me for career advice. Now that theviewfromjq.com is up and running, I'm sharing it from the vault!

Recently, a lot of people have been asking me for my opinion on what to do with their lives. Usually, my answer is "I don't know – what do you want?" After having many of these conversations, what I think people are really asking me is how to go about figuring out what's next.

I went through this decision-making process last year when I decided to leave the Go team and accept a new role as the Cloud SDK Uber TL. I hope that this post helps others going who feel stuck in the mud.

What you’re supposed to be doing with your career isn’t always going to be straightforward. There have been many times when I haven’t felt sure about what was next for me, and also unsure as to how to figure it out.

In my twenties, I switched jobs and career trajectories multiple times. With each transition, I faced an internal struggle that looked something like this:

1. Should I stay or should I go?

When I find myself unhappy for a long stretch of time, I'll start to question if it's time for a change. Having a life outside of work is important, but living only for the weekends makes life short and sad. 

This doubt is usually followed by weeks (probably months) of being stuck in the mud, wavering on whether I should look for new opportunities. To regain momentum, I'll take these actions:

  • Being upfront with my manager about what I want: Having an open and honest conversation with my manager about my discontent helps me evaluate if improvements are feasible within my current role. If the conversation is unsatisfactory, it usually means it is time to go. However, for me, it is important to give them a chance. That way if I do leave, I’ll know for sure that I explored all my options.
  • Asking for advice: I have many mentors whom I lean on for advice, and likely have been in my shoes before. These conversation help provide me with a fresh perspective and clarity on next steps.
  • Letting things fail: I’ve done a lot of glue work in my career that I’ve felt goes unnoticed and under-appreciated. Doing too much of this leaves me feeling undervalued. Letting things fail lets me reallocate my energy towards things that better serve me and bring me joy.
  • Exploring new opportunities: I often passively explore opportunities outside my current role, to see if I can find what I might be missing. Gathering this information has been valuable for evaluating whether my current job is really the best one for me.
  • Investing in new skills: One of the reasons I am often hesitant to switch jobs is because of the interview process. For the 7 months leading up to my Google interview, I carried a copy of Cracking the Coding interview everywhere and did at least an hour of algorithms everyday. I dread the day when I’ll have to spend my precious time like that again. However, working on the Go team at Google has been an incredible experience. Looking back, I’m so happy that my younger self did the hard thing and did those months of studying, so that my current and future selves can reap the benefits.

In case it isn’t clear, doing hard things is hard, and you will feel resistance about doing them. That’s okay! Be kind to yourself as you continue with that forward motion, and maintain a growth mindset that you really are capable of anything you put your energy towards.

2. How do I find where to go?

One of the hard things I mentioned doing is to exploring new opportunities. You might get lucky “holding the tree and waiting for a rabbit,” but actively pursuing opportunities has generally increased my prospects of success. These strategies include:

  • Applying for jobs: Sometimes I apply for jobs, just to see what comes back. When looking for my first software engineering job, I probably applied to about a hundred jobs, and ended up with 4 full-time offers. There is a long road between taking a few recruiter calls to actually signing that offer letter and walking out the door. Casting a wide net increases your chances of finding something given a lot of information asymmetry in the job search process.
  • Talking to people outside your network: You’re probably already telling your friends and families about your lack of job satisfaction, but you should tell your “weak ties” too. I got my job at Spring because I went out to grab drinks with a friend one night, and someone that happened to be there eventually became my first engineering manager at the company. I got my job at Google because I decided to start speaking at conferences, and ended up meeting two amazing Googlers who pushed me to apply. I was at a women in tech dinner the other night, and ended up referring two friends to an engineering manager at a startup I hadn’t heard of before that night. You never know who might be looking for someone like you to fill their next role, and talking to people outside your immediate network will statistically increase the chance of you bumping into the person who can change your life.
  • Doing things you naturally gravitate towards: There are things that you are naturally good at and enjoy doing, so do more of these things in more areas of your life. The more you do things that bring you joy, the more positive energy you will bring to your interactions with others, which can also help you figure out where you are supposed to be. If you don’t know what your natural strengths are, Kathryn Bishop’s “Make Your Own Map” book can be a useful resource. 

It’s hard to know which moments are going to be the catalyst that push you into your next big thing, but staying open to and seeking new experiences outside your immediate vicinity and comfort zone can help you find more of these moments.

3. What if where I go turns out to be the wrong place?

Once I’ve made the decision that I want to leave, fear and doubt usually creep in. Here's what I’ve struggled with before taking a leap of faith:

What if there is more left for me here? 

I’ve often had FOMO on what I might be missing out on if I left now. What if I’m unhappy now, but things get better and I miss out on something down the line? What if I just haven’t given it enough of a shot? Of course, there is no way to truly know the answers. But it is also why I do the hard things to evaluate if I should stay or go. This gives me that body of evidence to have confidence that I am making the right decision for myself.

What if the risk is too high? 

There is always a risk with changing things up, but there is a risk with staying too.

A year after moving to SF for my first job, I decided to leave and move back to NYC. At the time, it felt like the risk of moving back across the country could be an irreversibly wrong decision, and I agonized about it for a while.

I knew for a while that SF wasn't my city, and also had a feeling that I was supposed to be a software engineer. I loved the computer sciences class I took in college, and eventually, I moved back to NYC to go to the Recurse Center, which set me on the path I am today.

It was scary at the time to take this big leap of faith, and I’m happy it worked out the way I intended. Looking back, the risk of not leaving SF was really much higher. If the move didn’t work out, I could have always moved back. I was only a year into my career, and had plenty of time to explore new options. The trade off was waking up everyday, knowing that I want to be doing something different, and wondering if I should have taken the leap.

What if the grass is not greener on the other side? 

Leaving a job has always been an uncertain step for me, even when it was due to discovering pay disparities or a lack of growth opportunities. I was always scared of falling prey to the "grass is greener" syndrome, and that I would come crawling back for my old job. 

This is particularly scary as a woman in tech. At every job that I’ve had as a software engineer, there was always someone who made me feel small or less than, someone who tried to minimize my achievements by asserting that I was handed something, and someone who had undoubtedly equal or lesser impact than me, yet was paid significantly more. These experiences made me really scared to leave a job – what if the next place was even worse?

The truth is that no job is going to be perfect. However, it is also true that the world is a big place with an abundance of opportunities. Even if this next opportunity doesn’t work out, there's always another waiting. And for the one million bad things that could happen at the next place, a million wonderful things could too. 

At the end of the day, your career is your responsibility. If you wake up and don’t want to go do what you are supposed to be doing for too many days in a row, you need to do something differently.  No one else can tell you what you should do with your life, because no one else has to live with the consequences of your decisions. Wherever you choose to stay or go, I hope it leads you to exciting new horizons.