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I Walked into my Boss’s Office and Quit!

All of my troubles were solved and I could finally be my own boss. With one year of savings I ended my career of two decades and moved across the country to start my own business. In this judgement I was completely wrong. My troubles had just begun.

Shortly after my friend and mentor Tom retired I no longer wanted to have a lifelong career in retail. He didn’t get a Best Buy discount for life, he wasn’t offered discounted health insurance, from my point of view he barely even got any recognition. My managers told me Tom was the first person to ever retire from the company and the lack of support in place for this was astounding and disappointing. They couldn’t even answer basic questions about his stock option investment timetables.

Tom and I on my last day

An industry or company that had no plan in place for folks that invested decades into the company was not for me. I came to the conclusion that if I wasn’t going to work there for the next 50 years, why continue to work there for the next five? 

My job was great! I was respected by my peers, had complete control of my schedule, my tasks, and my work each day. But was required to be in the building 5 or 6 days a week for 10-12 hours a day. As much control as I had inside the building, there was zero control of where I worked or how often. No matter how efficient I was in my efforts, I had to be in that 45k square foot steel box, surrounded by florescent blue light, EMFs, and dust every-single-day.

I wanted a different future and could not be handcuffed for the rest of my life. 

After listening to Ben Greenfield’s podcast with Stever Robbins about quitting your job and reading Tim Ferriss’s book The 4-Hour Work Week I was inspired and uncharacteristically willing to take a huge risk.

Now, I’m not suggesting you do what I did. It was a horrible decision. Quitting your job with no plan except to live off your savings for a year and figure it out is naive. 

Getting my new business going was a lot more difficult and took longer than I expected. Savings go quick when you have no income. It is hard to start a new business in a new city where you have zero network. And in a county that is mostly retired folks finding a full-time job as a fallback is a lot harder than in a northern suburb. Oh, and people seem a lot less likely to take a chance and hire you as a consultant when you have no experience as a consultant and also have no job. Getting your first client is difficult enough and you want all the advantages you can get.


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Let the wise listen and add to their learning. (Proverbs 1:5)


I instead recommend doing what you do when you goto the pool. Dip your toes in to test the water before jumping feet first into the unknown. Keep your day job and start small by doing the work you are intending to do on the side. Start to build up a portfolio, start learning the skills that you are going to need, start going to networking events and meeting potential new clients, and find a client or make a sale to prove that your plan is viable. 

Retiring my name badge

Telling my boss I quit…

The dates were set, I was going to quit on July 1st and move on August 1. On the morning of July 1st my stomach was tangled up and every nerve in my body was tense. Was I making a mistake? I had drawn a line in the sand and I forced myself to hold the conversation that would have been very easy to avoid.

I found my boss and arranged a meeting to discuss “something very important”. Gulp!

He ended up being gracious, understanding, and completely respectful and appreciative of my plan. He said that someday he could see himself working for me! What a compliment. My nervousness was gone and I was elated. I knew something monumental had just occurred and that I was on the cusp of something new and great. All my reservations and fears were gone.

Flash forward to a month later, living in my new state… I didn’t know what type of business I wanted to start, I didn’t know what services I could offer or what real marketable skills I had. I knew I was great with people and sales, and I knew I could always fall back on another retail career or move back home. I had an escape hatch I could enter if necessary, but thankfully I never needed it.

Looking at my life now it is much different than it was. I don’t clock the same number of hours each week, but I definitely do more “work”. I am applying my creativity and strategic mind to more complex problems and have very little oversight on how, when, and where.

Consider this quote from Paul Jarvis’s, Company of One:

“But bear this in mind: achieving control over a company of one requires more than just using the core skill you are hired for. It also requires proficiency at sales, marketing, project management, and client retention. Whereas most normal corporate workers can be hyperfocused on a single skill, companies of one, even within a larger business, need to be generalists who are good at several things—often all at once.” 

I didn’t know what I didn’t know about being self-employed and had a lot to learn…

  • How to chase down overdue payments from clients and negotiating contracts
  • Valuing my time and work fairly
  • Saying no to distracting opportunities that come up because I have flexibility and “time”
  • Saying no to opportunities from previous clients that no longer value me as much as the market does
  • Finding new clients when 2,000 of them don’t walk through the doors every single day as they did in my retail store
  • How to get the watercolor aspect of the workplace I had in the corporate world
  • That nobody would ever understand “what I do for a living” ever again

I have learned all this and much more in the last four years and I have grown more than I did in my first 20 years in retail.

If I was to print a business card for all of the different roles I’ve held over the last few years I could fill an entire rolodex. I have grown as an individual. I have increased my market value and learned new skills that are important no matter what I do in the future. I love being able to chart my own course each day. There is no telling what I will be doing next, but I know that with a positive attitude and strong work ethic I will succeed.

My retired name badge

One reply on “I Walked into my Boss’s Office and Quit!”

You are a great story teller, James. And this post is a great first chapter of the adventure to come. It takes courage to leave a comfortable (and good) situation for an unknown great situation. Keep learning.

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