Hi there — posting has been a bit spotty the last few months, with COVID 😷, holidays, a work offsite in Austin (hello breakfast tacos), and a subsequent cold from traveling. I also made it out to a beach ultimate frisbee tournament, which was a nice change of pace. Hope your year has been off to a good start. This is a post that’s been rambling around in my mind the last few weeks, especially as many people are on the job market. Enjoy!
Everyone has something that they feel is a gap or deficiency in their career experience.
The engineer who climbed the ranks at a well-known high-growth startup from straight out of school for 8 years wonders, is everything I’ve learned applicable elsewhere? Maybe I’d be more well-rounded if I had worked at a few more companies.
But the engineer who spent 1-2 years at each company wonders, what if my résumé raises red flags for hiring managers, and they think I won’t be in it for the long haul?
The startup founder looking for an employee role wonders if their experience will be relevant or valued, and what sort of title their skill set even maps to at a company that’s not their own.
The engineer who got into software later in life wonders what their career would look like if they had started earlier.
The engineering manager who spent the last 15 years at BigCo wonders if their skills are externally relevant. Will they be able to keep up with the hustle of smaller companies? And is it worth the uncertainty of playing the startup equity game?
The early-stage startup engineering manager wonders if they’ll be taken seriously if they apply for a director+ level role at a larger company. They’ve rolled out leveling, onboarding, and hiring processes, but never managed a team or org larger than 20.
The engineer who took a few years to care for her children wonders how the gap in her résumé will be perceived and if she’ll have to settle for a lesser role than she knows she’s capable of.
The examples above are all of software engineers and engineering leaders, but you could imagine similar scenarios in any field.
Everyone has alternate career paths that linger in the back of their heads, that from time to time, they wonder… what would my path look like if I had done things differently?
My own what-ifs
I try not to dwell on the past, but I have plenty of what-ifs of my own and career “deficiencies.” Here are a few:
What if I had continued deepening my expertise in Android development back in 2010/2011 and led Android at some company that’s now worth billions?
What if I had spent a few more years on a purely technical track before moving into management?
I’ve spent the last 13 years at early-stage startups as an engineer and engineering leader — what if I had gone for an engineering leadership role at a mid-size or larger company? What options would that open up?
I spent a few years in coaching and leadership development — what if I had taken that time to further my career at another tech company?
Moving away from a deficiency mindset
What would it look like to drive personal and career growth not from a place of deficiency that needs filling in, but from a place of genuine desire?
What brings you joy? What energizes you?
If you’re trying to change your career path substantially (eg go from big companies to startups), instead of telling yourself:
I should’ve kept more updated with the current technology
I don’t know how to build any of this from scratch
I shouldn’t have stayed somewhere so long
It’s going to be embarrassing when people find out what I don’t know
What would it look like to fully embrace these mindsets?
I have a wealth of experience to share about how technology and processes succeed or fail at a much larger scale
I’m looking forward to mapping my skill set to a startup environment.
It makes sense that there will be things I don’t know and will have to learn or ask people about.
I can supplement my experience with knowledge from teammates, friends, and mentors.
Owning your unique path
It’s easy to think of your gaps as deficiencies that you should fill in.
But every career (and life) has countless forks in the road — it’s impossible to have explored every one, and at each point, you made the best decision with the information you had available to you.
Hindsight is 20/20, and feeling regretful that you missed out on a successful startup opportunity is akin to feeling regretful about losing the lottery after the winning numbers are revealed.
What would it look like to tell your career history from a place of owning your path and the uniqueness of your experiences?
What that looks like for me is that I have the unique experience of having worked at a large company (Google), as well as building out engineering teams at multiple early-stage companies. Taking processes, projects, and products from zero to one is where I excel, tackling a steady stream of new and ever-changing challenges. Having spent several years training and coaching engineering leaders, I have unique insight into the tech industry as a whole and also what motivates individuals.
Now it’s your turn
Whether you’re on the job market, brushing up your résumé to start looking around, or happy where you are, here are some prompts to help make this mindset shift from a deficiency mindset to owning your career narrative:
Write down all your gaps, deficits, and shoulds. Reframe each one - what do you have to offer, and what would you like to learn?
Now from a place of owning your unique experience, what is the story of your career thus far? How does what you want to do next fit into that narrative?
If you’d like, send your version over to me, or let me know what you got out of the exercise. (reply if you’re receiving this via email, or directly to jean@jeanhsu.com). I’d love to read it.
Things I’ve been enjoying
Soups! Although Bay Area weather doesn’t change that much year-round, there’s a time of year when all I want to do is make pots of soup. Now is that time. Very into recipe-less throw-everything-in-and-see-what-happens soups.
Slowing down - with recent colds, I’ve been enjoying taking it slow and letting myself be cared for. The kids have been making me tea, sparkling drinks, and snack platters.
Weeding - after the recent rainstorms, our garden is full of weeds. The never-ending tedious work of weeding scratches the same itch as deleting code.
This is a terrific perspective and a great way to think about experiences.
Loved this. I tend to let what ifs take too much of my brain space and this is very helpful