10 things to do when you quit your corporate job (to work for yourself)

It’s January. Are you leaving your job to pursue your new dreams? If so – or if you have a friend who is! – here are some of my favorite practices and reliefs from my own path last year.

  1. Get Health Care. Check out Covered California or Stride Health if you’re in the Bay Area. Cross-reference the plan names on Yelp to weed out plans that will cause more harm than help. Apply well in advance (2 weeks+) of the date you need coverage to begin. Set up auto-pay and paperless communications immediately so not to waste later time opening envelopes and calling customer service. Remember: While this process may feel excruciating and annoying at times, it is ultimately a discrete task. It can and must be done. And it can and must be done, more easily today than at many times in recent history, by you.
  2. Embrace ‘CEO, Stealth.’ Your job wasn’t you. Your title wasn’t. And now it isn’t either. Lucky for you, people have been ‘stealth mode’-ing startups for years now. It’s not your job to be fathomable to other people. Embracing this quick title, particularly for webforms and other purposes (check-in at Amazon Coworking Loft, for example) can take the worry out of something that Really Isn’t Worth It. Don’t let anyone stress you out about what you now do. Take a leaf out of the Makespace Coworking playbook and answer ‘what I’m working on today’ instead of ‘what you do.’
  3. Call your friends. Your old friends have loved you for many years. They do not care that you are going through whatever transition or feel scared or sad today. In fact, they probably don’t know what you are, were, or want to be doing on a day to day basis! This is an opportunity, because they love you but are outside the immediate ups and downs of transition. Call them back up (even if you haven’t talked in awhile). Say hey, tell them what’s up, ask and answer what you are each most excited about and what’s your biggest challenge. On the phone or in person, you can be real and human in a way you’d never want to post on LinkedIn or Facebook, so do it!  In the next few weeks, you’ll be in each other’s thoughts, then you can also passively spread a real word net (anonymously) to each of your networks for surprising, wonderful ideas and tidbits that might inspire your next steps.
  4. Check out a coworking space. If you’re like me, you might find this terrifying. Will it be inconceivably awkward? Will I stick out like a sore thumb? What’s the dynamic like? Where the hell do the coffee cups go? But really, you will never be as scared as the first time. Let this be a practice in doing something awkward, so you can re-grow your own protective skin around Doing Awkward Things, an essential tolerance for new or exploring entrepreneurs. If you’re really stuck, go to the Impact Hub on free day. Nobody will talk to you, you can ask questions to the host with the flag, and in a few days you’ll be over your fears and ready to no longer stay sequestered at home out of irrational fear.
  5. Go on walks. Get outside of your house. Go look at things or just walk down streets you’ve never walked down before. Notice things. Put your pants on. Observe strangers neither caring too much about you nor making active efforts to damage you. Exposure to your new world begins with a mindset shift. And opening up to a walk for walking’s sake is a great, very low-cost, zero-commute way to start opening up to that shift.
  6. Eat good food. Do you know how to cook? When was the last time you made meals for yourself? Brainstorm a list of all the things you know how to cook or the foods you used to enjoy before your job dried up all your time. Now, have a look at that list of ‘memory foods’ and see if there’s anything on there that’s both reasonably easy to cook and shop for and actually healthy. If not, you’re like me, and your parents’ food may not be the brain food you’re used to or craving. Ask friends who cook or a mailing list for some favorite easy dinner recipes and choose some with less meat, salt, or fried. Your body will thank you later.
  7. Pick an exercise method, with bonus points for structure. Go to yoga classes. Sign up for cross-fit. Do a very beginner dance class. Row, run, jog, walk, or lift. But whatever you do, find some way you can get into your body and help stimulate its demand for all those reasonable foods you’re going to be brainstorming. Classes or programs that require you to show up every week at the same time, and have accountability buddies, may be extra helpful for you right now as your life’s structure really opens up in a new way.
  8. Email people who are already freelancing or doing their own thing. Call them. Ask them for coffee. Churn your LinkedIn for names if you can’t think of any, or reach out to friends-of-friends or great authors on Twitter or people you encounter through that coworking space you visited. I didn’t believe it, but freelance people (and often people in companies too) actually do make habits of coffee and tea during the day. They don’t stress about it too much, and it’s a welcome break. Tell them what you’re terrified of. Either they’re scared too or they’ve been there and now they’re onto the next big fear. Listen to them. You don’t have to be able to help at this stage. One day maybe you can. But at this point, thanking them a million times for their past pain, buying coffee, and (bonus round) reflecting back one thing you learned from them, can very well be enough.
  9. Do something creative. Make a playlist each morning. Cooking can count. Pick up really weird creative hobbies you absolutely do not need to explain or justify to anyone. What to choose? Well, what’s one weird and random but fun thing you would never want to be caught doing? (Do that.) If you don’t have one queued up, go to an art store’s book section. Or, pick the first one of these that gives you feelings (good or bad) and get in motion: Chinese brush painting, typewriter poetry, a 30-second doodle from a pen you found in your kitchen junk drawer, charcoal drawing, solar carving, watercolors, dancing by yourself, arranging weeds/flowers you found on your walk home, coloring books for grown-ups, left-hand haiku writing. As Kurt Vonnegut says, don’t do it to make something, do it to find out what’s inside you.
  10. Let yourself quit. The path you’ve just embarked upon has lots of space and relatively little inertia or structure. A garden looks a lot more empty and vacant once you pull out the weeds. That does NOT mean it’s broken and badly in need of Whatever You Can Find To Plant Right Away. See if you can resist the urge to instantly fill every bit of space back up again. If begin to fear that nothing new will ever grow, lean on the supports above. But meanwhile, let yourself quit and just ‘be quit’. The human ability to tolerate irresolution is one of the hardest things to cultivate, but one of the greatest indicators of the happiness you can feel after a big scary transition. Don’t be afraid to let that window stay open for just a bit. Let yourself rest. Soon enough, you’ll be curious again for something new.

What did I miss? Post your favorites in the comments. Let the new world begin!

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