How should I think about my next job?
Spoiler alert: it involves more feeling than thinking
“Life has a way of making all your previous experiences make sense after the fact.”
– Chong Ki Kim [paraphrased from Korean]
Chong Ki Kim lost both of his parents when the Korean War started in 1950. After living with his extended family on a farm near what is now the border with North Korea, he fled south with friends to escape the fighting around the 38th parallel.
Soon after, deadly air raids left the seventeen-year-old Chong Ki alone, moving from shelter to shelter to find food as the country deteriorated. While running for his life, Chong Ki eventually found safety by working manual labor with the US Army’s 8th logistics team in Korea.
Chong Ki was later conscripted into the Korean Army and found skilled work by learning to become a driver. You couldn’t call AAA when your car broke down in war-torn 1950s Korea, so Chong Ki was also trained to fix engines, transmissions, and anything else related to operating a vehicle too.
With dreams of providing better opportunities for their five children, Chong Ki and his wife Ok Hee moved their family to Los Angeles in 1974. Chong Ki had worked mostly white-collar jobs over the previous 20 years, but like many immigrants at the time, Chong Ki and Ok Hee supported their family with manual labor and gardening services in the neighborhood.
To make extra money, Chong Ki would buy broken lawnmowers at the flea market and repair them for a quick flip. “I could fix a four-cylinder engine on trucks back in Korea, so a one-cylinder engine was easy,” he says with a smile.
The lawnmower repair business eventually became Lomita Lawnmower Shop, and Chong Ki and Ok Hee were able to realize their dreams for their children. They provided a college education for all five of their kids through that business, and today they rent out their shop and the land it’s on to cover their monthly expenses.
When he tells this story, my grandpa Chong Ki implores us to make the most of every opportunity. We may not know how today, but a greater reason for learning certain things may be revealed to us in the future. For him, a skill he learned across the world in exceptionally different conditions became the foundation that supports his life to this day. What can we learn from his experience?
You can only connect the dots looking backward
"We drive into the future using only our rearview mirror."
- Marshall McLuhan
My career prospects as a college graduate in 2009 were not good. In May of that year, the Wall Street Journal published an article titled, The Curse of the Class of 2009: For College Grads Lucky Enough to Get Work This Year, Low Wages are Likely to Haunt Them for a Decade or More.
Nice.
I was lucky enough to get work that summer as a telemarketer selling season tickets for the LA Clippers. The wages were low, and my place on the team was lower. The morning of my first day, I was led to a desk where I would begin cold-calling strangers from 9 to 5 out of a four-pound phone book. Yes, my lead sheets were the yellow pages.
This is not what I pictured when I was in college, but it was the education I never got. Getting hung up on and berated several times a day wasn’t my favorite experience, but grit set in quickly. I realized it was a numbers game and found ways to optimize for speed. I listened to calls with the better closers to hear how they pitch. Most importantly, I learned that selling isn’t showing someone what you can offer; it’s understanding their needs and explaining how you can meet them.
At that point, none of the paths available to me would have included my current job as a venture capital investor. But the experience helped me get a sales assistant job at a bank and eventually an internal transfer to a trading desk in New York. When I moved to Warby Parker in 2014, we launched SMS checkout years before it was normal because of insights from customer research calls. It was my sales director at the Clippers who first taught me to ask open-ended questions that get people talking.
Today, I find myself doing cold outreach and trying to understand people’s needs more than I have since my telemarketing days. I couldn’t have known it when I was smiling and dialing in 2009, but as I look back on it now, I’ve built on the foundational education I received in the salesroom at every career stop of my life.
Make the choice that’s right for you right now
“People naturally resist focus because they can’t decide what is important.”
How do you think about your next job? My guess is that at some point you’ve made a pros and cons list to analyze your options. You’ve weighed things like how much you’ll make, the industry, and the role. You’ve considered optimizing between the better salary and the better brand. You may have even rolled the tape forward to scrutinize how your choices will impact your life 2, 5, or even 10+ years from now.
I’m here to tell you that there’s no way to analyze your way to the right answer. To tell you not to treat your next career move as one that will determine the trajectory of your life forever. The thing that matters most is answering this question:
“What do you want right now?”
Ambitious people try to optimize their ways to solutions for challenging problems and our careers are no different. We agonize over trying to look into the future and understand where the path we’re on will lead. To complicate things further, what’s a high priority for our careers today will differ from what’s a high priority in the future.
But that’s the beauty of it.
There’s no way to know what will matter most to you later. Over the next few years you may move to a new city, start a family, earn a cash windfall, lose a loved one or decide you want to pursue creative ambitions that aren’t jobs at all. We all know people whose priorities shifted after one of these events and any one of them or more can happen to us too.
So before you hot dog fold a sheet of scratch paper and start scribbling down the good and bad of your next opportunity on each side, grab your journal and write about what matters most to you and why. If you know what’s important to you now and make the right choice for you today, the real career achievement will be finding alignment.
The people, purpose, place and pay will change throughout your life, but a constant will be you, navigating it as you. Trust yourself. Trust that you will make the right choice and that you’ll know when it’s no longer right. Trust that you can make the most of an imperfect situation (nothing is perfect) by adding to your skill set and learning more about what you enjoy. Trust that your choice will serve you and that you’ll make sense of it later.
Want to add an egg? [Optional footnote]
I realize there are practical elements of a career move. The little bit extra is a rundown of things you might consider for your next job, in no particular order. Remember: everyone has different priorities and yours will likely change over time.
Relationships
Teammates – who you work with at the company. Do they share your values? Do you enjoy spending time with them? Do they give you energy and inspire you? Are you collaborating with people who bring out your best?
Managers and direct reports – your reporting lines. Will you get mentorship from the people you report to and the people who report to you? Do you have complementary working styles? Is management invested in you and your career?
Customers – consumers, enterprises, healthcare providers, financial institutions, governments, etc. The type of customer you work with can impact the types of problems you solve and how you solve those problems.
Personal
Role – what you work on day-to-day. Is it below, above, or at your competence level? Do you enjoy the work? Are you making an impact that makes you proud?
Location – where you physically spend your time. Is your office in the city and neighborhood you want? Does the remote or in-office culture suit you? Is there travel? How do you feel about the travel?
Learning opportunity – how you will change as a result of this job. Are you learning new skills? Are you bringing your skills to a new industry or stage? What rooms will you be in where you can learn from osmosis?
Financial
Current compensation – salary and variable/incentive pay. Salary should pay the bills and make you feel valued for your contributions. Variable compensation should entice you to do more that helps the company on the key metrics that matter.
Long-term upside – exposure to uncertain financial gain. Long-term upside can come in the form of equity (options, stock, carried interest, etc.) or in the form of future earnings potential at this company or another one.
Capital structure – ownership and rights to profits. Is it private or public? Who are the investors in the business? Is there debt that might put the company at risk? Folks often underappreciate how capital structure can affect their long-term upside.
Market
Industry – the companies and people you work with outside the company. What does the company do and what role does it play in the broader industry? Does it suit your interests? Are there perks to working in it that mean a lot to you?
Stage – the company’s position in its life cycle. Is it an early-stage or a growth-stage company? Is it growing and taking market share or more mature and exploring new avenues of growth? Obviously, startups and public companies operate differently.
Brand – how people perceive the company. Is it known to be high-quality and do the people who leave have better or worse opportunities afterward? Is there a vision that motivates you? Are you proud to say you work there?