Here are some of the top questions I get about how to leave tech, also covered in the video.
When will I know I’m ready to leave?
First, your body will tell (or scream at) you. For me it was chronic neck pain and 5 migraines a week, both from tech neck. Emotional eating: on one occasion I ate way too much mac-n-cheese to get revenge on my job(??). I’m not sure how that works, but it’s real for many of us. I had insomnia and that panicky feeling that goes with it (although the insomnia really helped my book per month ratio). A couple times, I didn’t sleep a wink. I felt drunk during the work days that followed. I also, of course, had depression symptoms.
I know this sounds familiar.
The good news: these lifestyle factors often ease up, quickly, after you leave. Sleep usually improves first, which helps across the board. The tight muscles start to relax, improving range of motion, migraines, teeth grinding, etc. Eating becomes less involved, because work ain’t at the table anymore. Energy returns! The heavy feeling starts to lift, especially if you get professional help managing it. Hobbies resume. So do friends and family.
Obviously results may vary, but generally you can expect improvement once you’re out of the environment(s) driving you mad. Your body will tell you when it’s time.
Second, and assuming you don’t want another corporate job, you’ve started achieving income from your own business or non-retirement investments. You have a year of savings, etc. I call this “raising venture capital for your own self.” You wouldn’t want a friend to quit her job without securing ongoing investment in her next chapter, because you know she’d be in trouble when her savings depletes. And then she might have to go back into tech.
Apply that rigor to your own income, especially if you worked in go-to-market, commercial, strategy, or product roles in tech. Lock in that business justification.
Ideally, you’ll be making other income in the thousands per month. Don’t be like me and think you can become a full-time Substacker because you got a one-time $200 donation (thank you to that wonderful person!).
And check out this recent post by Charlie's Toolbox about magical thinking. It will help clock your own b.s. about investing in yourself — it did for me. There’s a worksheet companion too.
Third, sometimes you just gotta go. This was me. There was no other income. I was the breadwinner and the benefits provider. But I was having a nervous breakdown. The unlock finally came when I realized I couldn’t keep my work happy and improve my mental health. So I chose myself — without a plan. Because I love her and needed to intervene. I came to my own assistance, dramatically increasing trust in myself.
What should I do while I’m riding it out?
Stay with me for a sec: if you’re not yet in the middle of a career nightmare, you’ll need someone to help you when you are there. Ideally, you’ve already established some trust and rapport with this person. They know your background and goals — maybe even your typical patterns. If you don’t already see a therapist start now, for your future self.
Think about it: will you really want to explain your background to a professional week after week in 50-minute increments when you’re at your lowest? Shit no! So get ahead of it and make the investment now. It wasn’t until I was 8 years into therapy that I realized the gift my 29-year-old self gave my 37-year-old self. Now that is self-love.
Next, test one income replacement idea. No more than that, because testing multiple things at once gets messy — as you know from your UX co-workers. See if you can replace 1/5 of your monthly income, then 1/4, and so on. The higher it gets, the easier your decision exit timing will be. Word of caution: when you’re testing income replacement, this means talking with potential and actual customers. This does not mean creating a brand, setting up a business website, etc. A landing page is fine. Don’t be like me and waste precious time on activities that usually come 2 years in — or at least after achieving consistent market demand.
Now let’s talk about disengagement at work, a coping skill I relied on personally to just make it through. As a former practitioner of disengagement, I want you to know that there’s a hidden cost. When you practice disengaging, the flip side is often compromising on your values. And that wounds the heart, which makes things worse. So if you need to disengage, do this first. Identify the values where you won’t compromise and those you don’t mind compromising as much.
For me, I was not willing to compromise on advocating for my team, but I was willing to on continuous improvement. Both values were uniquely me, but I could survive without the former — I didn’t see my future at the company anyway. So why would I care about improving it?
Do a values analysis so you can figure out your internal boundaries when purposefully disengaging. It keeps you better aligned with your values than disengaging generally.
That brings us to networking. Don’t disengage (ha)! Hear me out. I have a reason. You know how a planted seed might take 3 months, 6 months, a year to start growing? plan for this timeline as you start exploring your next chapter. That looks like telling your favorite former co-workers that you’re looking. Maybe they went to a company they love and want to refer you. Maybe they’ll ask someone about an opening at your target company at that family wedding 4 months from now. Don’t fight the timeline here. You know that career help isn’t instant gratification. So put in the time now to network, so the benefits will be there for you down the road.
If you start networking when you’re desperate, your network will be turned off and you’ll weaken your position — or you may even damage some relationships. So start letting in the people you trust, and tell them, specifically, what you’re looking for next. Or promise them an update on X date when you plan to know then.
Lastly, do your doctor appointments while you wait it out. Prioritize the OBGYN and their recommended tests, a mammogram when over 40, the eye doctor (if you wear contacts/glasses and need a new 1-year Rx), and the dentist. Get the procedures, x-rays, etc. done before you have to switch insurance providers and while you’re still on that top-notch corporate insurance. This will free you up if you need to be on lower quality insurance for a year or two.
Wait yeah, wtf do I do about healthcare?
Your worry is valid. It’s horrible that healthcare is tied to work here in the U.S. — and often not even then. It sucks that your future is chained to it.
So do some grieving work (about how shitty this is) through journaling or talking to a friend or therapist — especially if you’re the breadwinner and healthcare provider for your family. Acknowledging this pain and pressure helps you see things more clearly, rather than staying stuck in rage.
And then, before you ever assume again that you have to stay in a bad job for healthcare, I want you to go to healthcare.gov and get private and public marketplace insurance quotes. If you don’t know what the alternative is, then you can’t complain about being stuck. Here’s my example:
I used healthcare to justify staying at a company I didn’t like for years. But then I checked out the marketplace. Most recently, my public marketplace insurance was $791 monthly for me and my wife. The plan wasn’t great, but it gave us some peace of mind. And since we completed tons of healthcare stuff when I was still on the good insurance, it was okay (for us) to sacrifice on that front.
So get that monthly quote. Once you have it, ask yourself “Is this amount worth me leaving my job?” If yes, then you just unlocked a new option as you build your exit plan. If no, then you have more clarity: riding it out or a longer runway might be best.
X condition should change things, so I’m planning around that. That okay?
It depends. Do you have control over X condition? If yes and you’re motivated to achieve it, then it might be okay to plan around that condition. Examples: if getting a new certification will unlock your desired career path, then plan for it. But if you don’t have control over that condition, then you might not want to plan around it.
For example, let’s say your former boss is recruiting you to join their new company. You’re excited, you just have to wait for next steps. But imagine that the company freezes hiring. “When will it unfreeze?” you ask your former manager. “I’m hoping Q2.” “Ugh.”
You do not have control over other companies, other people, and other opportunities. You only have control over your own actions, beliefs, attitudes, focus, and perspective.
So here’s the best play: reduce dependencies on others as you architect your next career chapter. That will speed things up. If you need to stay focused on those opportunities out of your hands, then at minimum, don’t put all your eggs in one basket.
Active planning > hoping for the best
Many of us (myself included) loop on existential woes when we’re suffering. Instead of giving into that seduction, which buries us even deeper, channel that energy toward building your exit plan. And give yourself rewards to stay motivated. Making those two changes (active planning and rewards) will get you out faster and on steadier ground.
Tell me in the comments: what are your questions about leaving tech? I’ll be doing this Q&A monthly, so give me all the new questions.
Rooting for you,
Rachel
