I Am 365 Days Free From My 9-to-5

A brief reflection on the ups, the downs, and everything I've learned in between.

A year and two weeks ago today I gave my husband the fright of his life by coming home from the job I had started four months prior and announcing I wanted to quit. He sat up, alarmed, my tears having given him the impression that there had been a death in the family or some other grade-A emergency. His relief quickly settled into panic as he registered what I had just said. 

I’m quitting. 

(And I didn’t have anything else lined up.) 

But how are you going to make money? He asked, thinking of all the adult things we are responsible for together, like the house, cars, and credit card bills.

I’ll work for myself, I said, thinking of anything and everything I could do. 

I was so confident. The kind of confidence only desperation can breed. The blinding kind that lets you levitate, leaving rationality behind as you float blissfully toward Cloud 9. The same kind that eventually peters out and sends you crashing back down. to earth. 

I didn’t think it would be easy, but I thought that because I already had ideas I therefore had a head start. Boy, was I wrong. In the roller coaster that was my first year of entrepreneurship I learned a number of valuable lessons, but here are the three biggest.

1. Don’t try to do too many things at once.

The first thing I did after quitting was, well, everything. I decided I wanted to be a freelance copywriter and revamped my old calligraphy-focused website and Instagram account, positioning them for my target market: interior designers. I researched potential clients and even pitched a few. I wrote blog posts for said website with accompanying Pinterest and Instagram posts. I started not one, but two Etsy shops, spending hours making the digital products. I started writing and self-publishing on Medium with the goal of getting into the Partnership Program and making a few bucks. They were all decent starts, but I had underestimated one critical ingredient for success: time. Not just my own, but time to exist. I was expecting immediate results. Call me a product of my generation, an impatient millennial, but I thought that standing these things up and getting them started would be enough. And because I had started so many things, I couldn’t do any of them as well as I needed to to make them take off. The only thing I succeeded in was re-burning myself out.

2. Give yourself permission to heal (and don’t, for the love of all things good, listen to your ego).

With burning myself out came all the trauma I had been repressing. Earlier that year I suffered a layoff from a company and job I loved. It was a blow that knocked me off my feet and cut me deep to my core. I tried to look at it from a more positive point of view, writing about my experience and getting a decent reaction when I shared it on LinkedIn. The post even landed me my rebound job. I was flattered when someone high up from my previous company approached me and offered me a role at the startup they had joined. But the flattery wasn’t enough. Despite still feeling a tad lost, I was starting to enjoy my freedom and the thought of starting a new 9-to-5 role – one that also required in-office attendance and therefore a commute – felt suffocating.

After the recruiter called to give me the offer, I hung up and cried. I knew in my gut – in my soul – that this was not what I wanted, but I was letting my ego take the lead and doing it anyway. It felt like the ultimate betrayal and I mourned the loss of myself, my free time, and my boundaries. Every day I drove into the city, the more I realized I was driving myself crazy. Sitting in traffic or in a near-empty office was not how I wanted to spend my time. I’d had a taste of freedom and I couldn’t go without it any longer. A mere four months after starting, I did what all Boomer parents tell their millennial children not to do: I quit. Given the worried response from my husband (see the intro to this article), I felt pressure to bring in an income, to say see, look, I can do this. But when all of my attempts failed, I, too, felt like a failure. In racing to make something pan out, I was slowly sprinkling salt in the wound I had never healed. It had been months since the layoff, but suddenly it felt fresh again. Without a direction or an income, I felt worthless.

I had a therapist, but even she agreed I needed more support. Per her recommendation, I sought the help of a life coach, something I’d only ever really seen portrayed in those few episodes of Gilmore Girls (if you know, you know). If I needed a therapist and a life coach, did that mean I was somehow more damaged and neurotic than Paris Geller? No, I eventually came to realize, it didn’t. That was just my negative self-talk doing what it did best (i.e. make me feel like shit). My coach was exactly the person I needed to help me rise above it. She gave me something I had been withholding from myself: permission to heal. It doesn’t matter how many months it’s been since the layoff, she said, you’re still hurting. All you have to do right now is let yourself grieve. I hadn’t known that I needed to hear it – I hadn’t even known I was preventing myself from doing it – and it made all the difference.

3. You’re still learning.

The last and probably biggest lesson I’ve learned is that I’m still learning. In a way, I’ve come to realize, there’s a freedom in that. As a chronic perfectionist, knowing it’s ok to learn alleviates some of the pressure I tend to put on myself to get it right on the first go. If this last year has taught me anything, it’s that you can’t predict anything; you can’t possibly know all the steps and check all the boxes before you begin. You have to try – you have to fail – to learn what you like. I’m learning that what feel like false starts or dead ends are just information – they tell me what ignites me, or rather, what doesn’t. In the long run, I’d rather be aware of those so I can steer myself in a better direction. I’m learning there is more than one route you can take to get you where you want to go.

This year was only the beginning.