What Should You Do When You Fail at Quitting Your Job?

Note from Caleb: I've been hard at work for the upcoming launch of Make It Rain (just a week away!), so I've asked a few really interesting people to share their journeys into the world of entrepreneurship and self-reliance. I hope you've been enjoying them. I have some other great ones coming up as well. Today's cubicle renegade escape story is from Melissa Anzman.

I joke that I am a failed quitter. The first time I went from cubicle dweller to business owner, it didn’t stick. So, I have had to leave the corporate world twice before I had enough knowledge and experience to sustain an actual business. For me, giving up was never an option, it was just a matter of figuring it out.

I knew early on in my career that Corporate America was not for me. I started climbing the ladder with the intent of getting out as soon as possible, but along the way I got wrapped up in the money, my title and the stability of a steady paycheck. So I kept on climbing until I just about snapped.

Instead of losing my marbles officially, I planned my first exit strategy… which varied greatly from my second time around.

My First Attempt at Quitting

I had been known to take career risks along the way, but I was finally ready to throw the corporate world firmly behind me following a near-meltdown in July. I was on a bonus-contract through the end of the year, which provided me with a solid deadline – I could not leave the company before then without owing them a lot of money, so instead, I used that date as my “get free” deadline. With six months to plan in advance, I went about creating my exit strategy, focusing on all of the wrong things.

My main goal was to save as much money as possible – putting my high-salary to good use and cutting down on my miscellaneous spending. I had an arbitrary number in mind of having $40,000 saved in liquid savings to cover my costs and any unforeseen emergencies for the transition I planned.

That was literally my ONLY plan – I did not have anything else figured out: where I would live, what I would do, what my own business would actually be, how I would earn income, what my freedom would actually be like.

My mindset was that I wanted to be my own boss and if it didn’t work out, I could always land another corporate job.

And that is where it all went wrong. Every morning I would sit at my computer and spent hours pondering what my business was going to be and different ways to earn income. I even launched a website, the first that I fully designed, but never went all in and didn’t make a single sale. I was so busy being stuck in analysis paralysis that I ended up having to get another job to pay my bills (note: I did not spend all of my savings, but I started to get nervous and bored).

So I transitioned back into Corporate America.

Second Time, Make it Count

The first day back in the office, was soul-crushing.

It was worse than anything I ever felt before – I knew I wasted an amazing opportunity to follow my dream… because I never figured out what my dream was. So back to work I went, but I did it strategically. I accepted a “bridge job” position so I could earn a steady income, but also have the time and mental capacity to build my own business. And I put myself on notice – I had a new deadline, but I made sure I applied the lessons I learned the first time around.

My new plan to quit was structured. I had a quit date; a money saved amount ($10,000 this time around); and business milestones.

I was not allowed to leave my corporate job until I had a fully functioning business that was earning income (I had a specific income target, number of clients, and number of website visitors). And with it, I removed the final safety net – when I quit this time, it would be for good.

There would be no “going back to a corporate job” should my own business not work. It had to work.

5 Lessons I Learned from Being a Failed Quitter

  1. Leaving the safety and security of a corporate job is not easy and cannot be learned. I was constantly searching online for ways that other people made it work. The steps that they followed to lead me straight to success. I tried to find a secret hidden formula. I finally realized that it was different for everyone. I never thought I valued the security that a corporate job had, but that was one of the hardest things for me to part with when I ventured out on my own. The work schedule, responsibility of covering everything, the lack of constant interaction – all things I enjoy now, but they were difficult to adjust to during the transition.
  2. Having a viable plan in place is key. I was asked by a fellow entrepreneur who promised some advice (it never did come by the way), to review my business plan. Uh, I didn’t have one. And while it has only been referred to a few times since launching my business, the process of creating a plan and thinking through the plan, was critical to my success. “If you fail to plan, you plan to fail” – great advice… I wish it didn’t take me so long to apply it!
  3. Money saved does not equal success. There isn’t an exact number that will ensure you can pay your bills. I had a magic number in my mind of what would help me be successful, and it didn’t matter. It is not about the money saved or the cushion you have – it is about the viability of your business and ideas. And if you are like me, the less money you have, the more creative you get – so the pressure has helped my business become successful more quickly.
  4. Take the comfort of stability to tweak your business and idea, without the income pressure. Being able to test your ideas out before you are counting on them to sustain you, is ideal. It allows you to figure out what you like and dislike, and work on your funnel and strategy without taking huge income hits. Having a side hustle is a pain, but the outcome is worth all of the juggling.
  5. Clearly knowing what makes you tick, will drive your success. When you know what motivates you, particularly when it comes to work, it is much easier to build your business to support your motivating factors. For me, being on my own was more about freedom than income – so not making as much money (yet) as my corporate job, is easy for me to live with. Getting to the root of your motivation will help sustain you when you do finally make the leap – you will have a constant reminder of WHY you are on the path you are on.

Am I glad I had to quit twice? Absolutely.

It was a hard road, and it is embarrassing at times, but I learned more about myself during my first “sabbatical”. Through those lessons I have since created a sustainable business (or two), and truly understand what it takes to be my own boss.

Melissa Anzman is a career coach, blogger and author of Stop Hating Your Job. A former human resources insider who helps people fall in love with their jobs again, Melissa blogs at Loosen Your White Collar(img)

Money, Work, Reader StoryCaleb Wojcik