#14: How Do I Know If It's Time to Leave My Job?
Let me tell you about my orange theory. (Not to be confused with...Orange Theory.)
Hello Hayes,
I have been at my company (a Series A tech start-up) for a year and a half, and it’s largely been awesome. The company is growing rapidly, I like most of my coworkers, I have a lot of responsibility, title clout and room for growth.
Buttttt, I’m underpaid and overworked. I make a decent living but do believe I can make significantly more elsewhere. It’s hard for me to fully take the plunge to pursue leaving, because I feel very tied to the success of the company, and I (likely naively) believe they’ll take good care of me. Also “the devil you know.”
How do you really know when it’s the right time to leave, especially when your current role checks off several major boxes that define what it means to “have a really good job”? I can’t quite imagine leaving because of my stake in the company and feelings of “what I’ve built” and “what I can still build,” let alone the feeling of regret if the company continues its trend of hyper growth and I miss out on a huge payday. But I really want (read: need) more money and more flexibility. I need work-life balance. Is it possible to find a job with 50% more pay and 30% less work?
It can’t be healthy to be thinking about work at all hours, answering “quick Slacks” or being generally available all the time. But is this what’s required to grow a career? Is my drive for success serving as a figurative enabler of unhealthy habits?
Yours,
Happy to Slack, Happier to Sleep
Hello Happy to Slack, Happier to Sleep
I have this video of myself from 2017, the week before I quit my first job. I’m laying on my bed in a yellow sweater. I am exhausted and swollen and gray, my voice low. I say, “I’m taking this video in case you ever need a reminder of why you made this choice.” (Proof that long before I started sharing my work online, I had an instinct for documenting big moments.) This was the first time in my career where I was deeply burned out.
It was ironic because my burnout came on the heels of a nice bit of success. I had just won a prestigious national teaching award. Why, you might wonder, would I quit a profession that I was just recognized for being pretty good at?
The answer was simple though devastating. I quit that job because I had to. I had become a shell of myself, I could not sleep, I was irritable and absent with people I love, including my students.
Sometimes you quit your job for those reasons. You quit because your life requires significant change if it’s going to continue — and it must continue.
But other times, even when you feel burned out or irritable or are having trouble sleeping, it’s not yet time to quit. I’ve had three full-time jobs in total, including that first teaching one, and there were moments in the next two where I felt similarly to how I did when I recorded that depressing video. I didn’t quit though, not right away.
Instead I applied my orange theory: Think of your job like it’s a big fat juicy orange, with a finite amount of juice to be squeezed. Some are Sumo and plentiful, and others are Clementines — there’s less juice from the get go. Some are deceiving: You think it’s a small orange and the fruit has run dry, but then you flip it around and realize there’s still a pocket of juice left to give if you squeeze it just right.
If a job is an orange, then you leave when there is no more juice to squeeze. But before you toss it in the trash, you need to make sure you’ve squeezed all of its sides. Sometimes when we feel miserable at work, ready to quit, what we actually just need is to approach it from a different angle.
This analogy has been fundamental in my life, and hopefully in the lives of all the people I’ve shared it with over the years. Reading your story, Happy to Slack, it sounds like there is still juice left in your job. There’s juice in the form of equity, relationships, new experiences and responsibilities. I hear though that you want the kind of juice that makes life a little more leisurely: you want money and time. Which is fair. Do you know, for a fact, that you cannot get those things in your current job? Have you communicated recently that you are looking to be compensated more for your work? Have you had a frank conversation with your boss about introducing more flexibility to your schedule, in ways that not only benefit you but also benefit the company? (It pays to be good at spinning things, which, if you work at a Series A tech start-up, I’m going to assume you are.) Being able to ask these questions is a privilege, but I’m taking liberties here to assume that you might have them in your role. If you haven’t yet, or you haven’t recently, I urge you to have those conversations. Make them say no. Or let them surprise you. You cannot control whether they work with your wishes, but you can control whether you even try to make them come true.
You talk a lot about work-life balance and boundaries in your letter, about feeling “always on” even when you are quite literally off. You’re right: Start-ups and other high-pressure environments breed and reward this type of behavior and addiction to work. But we also nurture the behavior in ourselves.
This is always what I’ve found hardest — not just setting boundaries with the people I work for and with, but respecting the boundaries I set with myself.
It isn’t so hard for me to say to a client, I don’t check e-mails on weekends, but it is hard for me to not actually check them.
Yes, “the workplace” and capitalism is the system that created a monster in me, but I have still been its ultimate shepard. I say YES and I CHECK MY PHONE and I DO EVERYTHING I NEED TO. But sometimes, looking back, I didn’t need to. I didn’t need to check my Slack when I went to the bathroom at dinner. I didn’t need to work on Sunday just to get ahead.
Be honest with yourself: Are you in a job where you really need to do all that? Or are you breaking your own boundaries and in fact, you might be part of your problem? I hear your answer already: A little bit of both, Hayes. I think it’s a little bit of both.
You talk about this behavior and ask, “is it what’s required to grow a career?” For some, I think yes. I think it’s what’s required.
I got coffee with a dear friend recently, an entrepreneur who is by all definitions *extremely successful* but is still on his way to reaching his peak success. Both of our phones were tucked away as we cracked out on cold brew. We spoke of our work, our ambition, our experience, and he said that he has only just gotten to a place where he’s earned the ability to put his phone away in a situation like the one we were in. That only now, after slogging for years working for others and in the last few building his own business, that he’s afforded himself that right. In the weeks since, I keep coming back to that notion, the idea that “making it” in this day and age could be defined by being able to get coffee with a friend on a weekday without your phone in sight.
This was a fact for him, needing to be plugged in at all hours of the day in his former jobs. I think a lot of people think it’s a fact for them, too. But it might not be. For them, nothing would really happen if they didn’t check their Slack or email for two hours during the day. Their anxiety might spike! Their boss might be confused at first because typically they respond in 30 seconds! But there’s a solid chance that nothing career-altering would occur. Except maybe they’d become happier.
There’s also the reality of the truly toxic work environment, or the deeply burned out person, which I don’t think you can just pomodoro method your way out of. In those situations, there’s no more juice left to squeeze. Your orange is not just empty, it’s molding. That’s definitely someone’s story — but it doesn’t sound like yours.
Can you find a job with 50% more pay and 30% less work? I don’t know what you’re getting paid. If you’re really getting screwed, then yes, I think you can. I don’t think it’s the right question though. We think more money, less work will make us happier, but it doesn’t. Instead, I think happiness is when we earn the right amount of money for the right amount of work, and crucially, for the right work.
You could have paid me 3x the amount of money I was making in my last job, same amount of work, and while I would have had access to things that might make me happy — I’d fly first class when I travel home, maybe we’d buy a house — I would not have been any happier because I hadn’t figured out what my idea of a “good job” was. I was working based on everyone else’s definition, which turns out to be fundamentally different to one that is authentically me.
This is why I think, first and foremost, you need to narrow in and align on what you want. Stop wasting your energy stressing about whether it’s the right time to leave. Free yourself from the pressure of making a decision. Channel your focus into identifying what you actually want in this era of life. Is earning more money the most important thing for you right now, or is enjoying your summer with a job that’s predictable, albeit disappointing sometimes? Once you have your definition, hold your orange and see if there's juice to squeeze in those areas you’ve identified.
There’s one more thing that we didn't talk about, but it’s important. You believe your job will “take good care of you,” which it might, but do not confuse that possibility with real, genuine human care. Your job does not love you. It cannot love, it is not an animate thing. It has no personality or morals and it owes you nothing. Remember: You’re the one squeezing it dry. When the ship is sinking, your job is jumping in the lifeboat while you slide down the deck. Do not confuse your loyalty to your job with your loyalty to your idea of success. The false promise of a “good job” is what you’re loyal to, but it’s a hollow plague that’ll trail behind you until you look it in the eyes and tell it what it is.
What is it?
Yours,
Hayes
Send me your advice letters at alexandrahayesrobinson@protonmail.com
Bravo ! bravo!!!!
So incredibly helpful. Love