How To Opt Out Of The Career Ladder

The art of taking your first steps off the “conventional” career path.

About the author:

Jean Hsu

is the writer of

Tech and Tea

, a startup VP of Engineering, leadership coach, and mom of two.

When someone is described as being “really successful,” people usually mean a societally agreed-upon flavor of success, driven by status and achievement.

To its credit, this definition of success does provide a lot of clarity on what to do next at each step. 

• You’re a student? Get good grades, ace your SATs, and apply to prestigious universities.

• In college? Apply for elite internships. 

• About to graduate? Go for the best job you can (i.e. intersection of a reputable company and high-paying).

• Working full-time? Strive to level up through promotions and checking off the leveling system’s boxes. 

• Working as an IC? Climb the IC levels and then try to move into a leadership position.

• At a lesser-known company? Apply for more reputable companies.

The gist of most career aspirations: Make more money, have more impact, and leave a legacy.

This is a reasonably clear way forward.

What If The Ladder Doesn’t Feel Right?

More and more, I’m finding that people further along in their careers are no longer motivated by the conventional career ladder. 

The choice between hustling to have a more senior role at the same company or hustling to either have the same role at a “larger/better” company starts to feel like not that appealing of a choice.

Once you get off the “proven” career path, you have to figure out for yourself what road you want to be on, and that can be terrifying, like veering off a well-trodden hiking trail and risking being lost in the forest.

Particularly in tech, people commonly fantasize about quitting tech to do some combination of making things with their hands via woodworking or art, opening up a small business in the form of a bookstore or coffee shop, or buying land to farm and live off of.

Perhaps less extreme departures from the VC-startup tech grind include moving into consulting or coaching, working in non-profits or govtech, or sabbaticals to travel and spend time with family.

If the conventional tech career ladder feels unappealing to you, but you’re not sure where to go from here, here are a few directions to start exploring. There is no one tool I can hand you to provide clarity on what to do next, but these are all useful to have as you navigate this next phase of defining your own path.

Get Clear On Your Values

When you’re mindlessly on the default path that is climbing a conventional career ladder, you’re also living the default values celebrated by that path. The “normal” path values things like achievement, financial abundance, leadership, career, and legacy.

To find your own path, it’s exceedingly helpful to get clear on what your personal values are. There are plenty of exercises, journaling prompts, and coaching engagements you can find to help you get clear on personal values, but just to start, take a look at this list of values. 

Say the values of integrity, belonging, and authenticity jump out at you as important. Then perhaps that startup with the CEO you got sketchy vibes from isn’t a good choice, despite your high confidence that it’s an early rocketship that will bring you financial wealth down the line.

In the absence of clarity around your own values, it’s all too easy to strive for the conventional “success” you see around you. 

This comparative tendency is particularly challenging in tech, when almost everyone knows someone directly or indirectly who’s ended up with a life-changing amount of money through founding a startup, being an early employee at a successful company, or… buying crypto at the right time.

Getting clear on your values gives you something to come back to when you’re tempted to compare your “success” with someone else’s.

Figure Out How Work Fits Into Your Life

For many high-achieving people, stepping away from conventional achievement does not come naturally. For much of our lives, our job is to do more, to get better grades, to get the next promotion. 

Unlike handing in a problem set when it’s due, striving for the next, bigger achievement never ends — there will always be a higher impact role, a higher valuation, and a bigger exit. 

This post is not meant to convince you to take a step back from that, but rather to be intentional about the role that work plays in your life.

Work Fits Into Your Life Differently At Different Life Stages

There may very well be times in your life when you choose to have work be all-consuming and play a very central role in your life, even taking up late nights and weekends.

In other seasons of life, work may play a more supporting role. An obvious example is when people become parents — that first year of parenthood has so many challenges that work usually takes a backseat. 

But parenthood need not be the only viable “excuse” for work to not be all-consuming. You may just want more time to work on your mental health, to learn woodworking, to care for a loved one, and to spend time with friends.

When thinking about the role you want work to play in your life, you don’t have to make long-term plans. You can just think about this next year or even six months. Here are some examples of setting intentions around the role of work:

“As I settle into a new home, I want work to play a supportive role — I’d like to do a good job and be an effective teammate, but I don’t want to raise my hand for additional responsibilities”.

“As I become a parent for the first time, I’m prioritizing spending time with my newborn. For this next year, I’ll plan to coast at work to make space for my new priorities.”

“I’d like to spend more time with family and friends. For me to make space for that, work looks like taking a step back from management and leaning into IC engineering work on a flexible remote schedule.”

“As my kids are getting older, I’d like my work to be part-time, so I’m available to them these last few years that they’re at home.”

You Shouldn’t Feel Guilty For Needing Things Work Can’t Provide

For high-achievers, intentionally deciding for work to play a less central role in their life can bring up a lot of challenging emotions — guilt, shame, stagnancy, and lack of purpose. 

We’re fed this story that so many of our needs can and should be met through our work — social needs, personal growth, desire for impact, desire to lead a fulfilling life. 

But many of those needs can be met outside of work, so being clear with yourself on what role you actually want work to play in your life is an important foundational step to exploring what’s next.

Notice What Sparks Your Interest

Start to notice what jobs, job arrangements, or people spark your interest. 

Perhaps you come across an engineering role on LinkedIn at a non-profit that you care about. 

Or maybe your friend tells you about their part-time consulting gig and how they plan to spend a few months hiking the Pacific Crest Trail after their next contract ends.

Or your former co-worker who switches to an individual contributor role after years in management.

Make a list. Jot down everything that sparks something in you.

This is just an exploratory process. It’s practice for noticing what you’re interested in, for starting to think creatively about what your path might look like outside conventional full-time ladder-climbing, where you’re bucketed into well-defined engineering and leadership roles that have been the default for so many years.

The career ladder exists because companies need some way to categorize people, to figure out how to hire them, pay them, and compensate them. The career ladder works to organize and make sense of tens or hundreds of thousands of workers at scale, but it doesn’t need to define your path.

Expect Skepticism

When I started a coaching business after leaving an engineering leadership role at Medium, more than one person asked me how it would scale (perhaps a side effect of being steeped in the VC ecosystem for so many years). 

What I realized was it doesn’t need to scale. 

I was just one person on my way to getting a few coaching clients. I didn’t need or want to grow a billion-dollar coaching behemoth. 

More generally, though, be prepared for criticism or skeptical thoughts, especially from those who are unhappy on their default career path,. That’s not about you — that’s them projecting their own fears onto you.

You’ll probably hear things like…

“Maybe you should just stay if it’s not that bad. It’s not a good market right now.”

“If you take a step back, how will you explain that on your resume?” 

“How will you get health insurance?”

You may experience skepticism from people in the tech industry, but also from parents and other well-meaning family members who built their careers at a very different time, possibly staying at one company and climbing the ladder for decades.

As you explore paths that aren’t clearly higher-paying, higher-prestige, or higher-impact, be prepared for off-handed remarks, but know that they’re not really about you. Find people around you who you can explore ideas with without getting shut down. 

Questions Whose Answers Will Help Get You Started

Some reflection prompts to think about or journal about as you explore your own career path:

• What values are most important to you? 

• Are you prioritizing maximizing your financial outcome? If not, what are you prioritizing instead?

• Do you want work to play a more primary or supportive role in your life?

• Do you want your work to be a main area of growth, or do you mostly want to lean on your existing skillsets and strengths?

• What are some career paths or people that have sparked your interest lately?

• Who do you trust to bounce ideas off of?

• When you look back on your life, how do you want to define your success?

Leave a comment with what you found helpful, and where you feel stuck on this path, or email me directly at jean@jeanhsu.com.

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Tech and Tea

, where I write about navigating life in all its messiness while also working in startups.

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