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7 Hard Lessons I Learned from Quitting My Job With No Backup Plan

In 2018, I was fed up. The misery was piling up at my job, compounded by an hour-and-a-half commute every day and a micromanaging boss.

My workplace was so toxic that people would come and cry in my office on a regular basis. 

So, when they offered me a raise and a permanent, full-time job there (I was on a contract), it felt like someone was handing me a pair of handcuffs. 

Here, put these on yourself. Promise us you’ll be stuck in this misery for a while longer.

I sat shaking in the bathroom for 10 minutes before I got the nerve to say to my boss what I was thinking. I called my wife for a pep talk from the stairwell, and she supported me.

And I walked into the office and said, “I’m sorry. This isn’t the right fit for me. I’m leaving.”

I could hear a voice screaming at me. What the hell are you doing? What if there’s not another job out there for you?

Here’s what I learned from quitting my job without a plan.

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1. A wish is not a plan

I’m going to start my own business. I want to be an entrepreneur. I can make twice as much money as a consultant than I currently make. And I get to be my own boss.

Have you ever found yourself saying things like this? That’s how I talked myself into quitting. 

I rationalized that I would make WAY more money as an entrepreneur.

Eventually, I did. But not that year. That year I sat on the couch and stared out the window in misery.

I had a dream. But I had no plan.

My advice to you, if you’re thinking about this, is to do all you can to create a cushion. Build up your savings account. Start reaching out to potential other jobs or clients.

Make sure you’re networking & using LinkedIn! (I have a video with some useful tips).

2. There are a lot of opportunities

The good news for me, that took me a while to learn, is that there were a lot of opportunities.

While I failed at entrepreneurship that go around, I did eventually land another job that paid slightly better.

There are a lot of opportunities out there. But the hardest thing can often be finding them. If you’re going through this stage, you can definitely apply on paper. But I would make networking the first priority. 

Have as many cups of coffee as you possibly can with strangers. Talk to everybody. Do informational interviews. That’s what will create possibilities for you.

3. Expect the money Gap

When I quit my job without a plan, we had about $5,000 saved. It seemed like such a nice cushion.

We burned through it pretty fast. 

If you are going to quit your job without a plan, do expect a money gap.

You can make it easier for yourself by constantly building your savings, and making sure you have anywhere from 3 to 6 months’ worth of expenses if you ever need to quit.

That’s a chunk of money that would cover most people’s average job search.

If you don’t have anything saved, start saving aggressively. Expect that there will be a money gap.

And whatever time you think it might take to get to your next paycheck, double it just to be safe.

At the time, I told myself that I just didn’t have enough energy at the end of the day to job search. And looking back, that might have been true.

But I’ll never know. Because I didn’t really try.

Job searching with an active job in itself can take a lot of energy, but it is a really good idea. You lose some of the desperation, and it puts you in a better situation to land a better job with more money.

If you have limited time and energy, try booking one or two networking meetings a week. Go for coffee on your lunch or before work (don’t expect to do your best career hunting at 9:00 p.m.).

Just by building your network and talking to people about your possibilities, you will find opportunities open up. 

If you’re applying for jobs and paper, don’t be so hard on yourself. And don’t pressure yourself to apply for thousands.

Pick a few companies you really want to work for and I focus your energy on applying for a couple of key roles that fit.

5. Switching jobs brings more money

Last year, I interviewed a bunch of people for a book project. They were all people who had doubled their income.

And apart from the entrepreneurs, I noticed something about people who doubled their income.

The biggest increases in income come at the point of job switches.

First, this could be because people move to a new job that makes more money. Which did happen a lot.

But also, when people tried to quit for another opportunity, bosses often offered more to keep them. 

This seems ridiculous, but it checks out. If you’re happily working and your boss doesn’t have to think about you, they’re happy to pay you your salary. When you start to leave, and they are faced with the prospect of replacing you, all of a sudden they’re willing to offer more–especially if you’re good at your job.

No, I’m not tempting you into a high stake game of chicken with your boss. But I am telling you that I did eventually land a job that paid about 10% more and came with benefits. Research shows that people who switch jobs often get 10-20% more

6. The struggle is in your mind

I never knew how depressed I could get until I spent the mornings in February sitting on my couch, staring out the window, getting ready to cry.

My fantastic dreams of entrepreneurship failed miserably, mainly because I had no idea what to do or where to start.

It took me 5 or 6 months to land another job. And I took it gladly, ending a miserable period in my life.

If you are quitting your job with no plan, make sure you line up some support. Connect with a career counselor. Plan to attend networking events. See a therapist.

Expect it to be a hard time and find the support you need to make it not so difficult.

7. A side hustle could have helped

Looking back, I’m not sure if I had the energy for a side hustle

I really don’t know.

But if I could have found something, it probably would have helped. I was working on this blog at the time, dreaming of making money from it. But I wasn’t. (I do now 🙂)

Building a side hustle, if you have the time and energy for it, can help to fill the money gap from leaving a job. 

(And I’m talking about a profitable side hustle here. Not an imaginary one. Not one that you work at that pays no money).

I could have started to poke around with business before I left the job. But I didn’t.

What I did the next time

The dream of entrepreneurship never really died. So I worked another year at the new job and dreamed about a future when I could work for myself.

When I eventually made the leap the next time, I had a client lined up. I cashed my first consulting check weeks after leaving a cushy government job.

I tell the story of how I made that leap in this video.

The big lesson I learned from all of this. There’s absolutely nothing wrong with leaving your job. Heck, it feels necessary in this economy. Switching jobs can earn you more, move you up the ladder faster, and help you find something that fulfills you.

I’m all for it. 

But I would never quit my job again without a plan.

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