Time to Kick Off My (Goody Two) Shoes?

I’ve always played it safe. Ever the goody-two-shoes, when other kids were cutting class, breaking rules and defying authority, I was the one more likely to be sitting quietly in the library working on a project for extra credit. I take my responsibilities very seriously and am by no means a risk taker. So, it’s no wonder that I’ve been losing some sleep lately about a decision I need to make. Don’t get excited now! I’m not about to confess that I’m about to rob a bank or even go through the express checkout with 11 items instead of the requisite 10. I’m talking about leaving a good paying job that I’ve had for 12 ½ years, without a concrete plan for the future.

I have been talking about this to family and friends for literally years. I never felt I had a justifiable reason to do it. I have a stepdaughter, but she never lived with us full time, so being a “stay at home Mom” was never an option. When our dog was alive, I used to joke about being a stay-at-home dog Mom, but people would have thought I was a lunatic. I knew that some people won’t understand my decision. They may think I am ungrateful, lazy, or selfish. Worrying about what other people will think is a hallmark of being a goody-two-shoes-people-pleaser, which is why I’m having so much trouble making the decision. Despite all the doubts, I finally feel like the time might finally be right.

My first 17 years after college were spent in accounting and bookkeeping jobs. Then, feeling burnt out, I decided to take a job as the office manager and marketing director of a small accounting firm.

There are parts of my job that I love. I interview our clients and write newsletter articles about their businesses. This feeds my creative side and has shown me that I can write compelling copy about even the driest, most boring topics. I lay out and write the rest of the newsletter, write press releases, and coordinate other marketing efforts for the firm as well.

My nerdy side loves some of the administrative tasks that I’m responsible for. I maintain complex databases and spreadsheets. I actually find tax season kind of fun (God help me!), maintaining schedules and overseeing the workflow for the office.

Sounds great, right? Well, for about 3 months out of the year, it is. Due to cutbacks and layoffs, my job duties have changed over time. My hours were cut to three days a week for all but tax season (January 1 – April 15). When that happened, I was more relieved than dismayed because the rest of the year is mind-numbingly dull and filled with duties I do not care for. I won’t go into details, but let’s just say that the job has changed enough that if I was interviewing for it today, I would probably turn it down.

I spend my days daydreaming about all of the things I could be doing at home. I have numerous projects in mind. Foremost on my mind lately is documenting my family history, including scanning and cataloging my parents’ and grandparents’ photos and researching my ancestry. I envision being able to give each of my siblings and nieces and nephews a thumb drive full of photos along with a written history. It would be a huge undertaking that I think would be important and fulfilling, but obviously would not provide a paycheck.

I also want to devote more time to writing. I’ve done a little bit of freelance writing, and would love to explore a career as a freelance writer, but a lifetime of playing it safe has been keeping me from doing much more than dipping my toe into that pool.

In analyzing my fears, I see that they fall into three main categories: security, ego, and self-doubt.

I know so many people who are, or have been unemployed or underemployed over the past several years. Many of them will think I am bat-shit crazy to leave a job that pays well, that I am good at, and that is only a ten minute commute from my house. But through a combination of being empty-nesters, frugality, and luck, my husband and I both agree it is financially doable.

But the security of a paycheck isn’t all that holds me back. I worry about feeling “less than” in the partnership that is my marriage. I was 36 when I got married and up until then was 100% independent. Even though my husband is supportive, will I feel like I am spending “his” money? How many home cooked meals, loads of laundry and trips to the grocery store does it take to feel equal to bringing home a regular paycheck and contributing financially to our retirement fund?

Then there’s the part my ego plays. At work, many of us, especially those of us in administrative and supportive roles, catch ourselves play the martyr – “all that I do for these people goes unappreciated and unnoticed! They couldn’t function without me – if I leave it will take two, maybe three people to replace me!” The reality is that people come and go all the time, and businesses don’t crumble without them. How will I feel when they either hire someone else or when I find out they simply discontinue some of my initiatives because they don’t find them necessary or important anymore? This may sound like a frivolous concern, but no one wants to feel like they were of little or no value.

Then there’s the big boogieman known as Self-Doubt that is lurking around the corner. What if my writing isn’t really good enough and no one wants to hire me? I’ll need to get out there and market myself – something that sounds scary and more than a little daunting. I will need to be driven and determined. I have a hard time putting fingers to keyboard often enough to write this blog; I will really need to step up my game if I ever expect to get any work.

I would like to approach my boss with the idea of ending my day-to-day work and becoming an independent contractor for him instead. I could still do his newsletters and other marketing projects on a freelance basis from my home. Maybe I could even come back to coordinate things during tax season.

I realize that I’ll be taking a risk. He and the management team may decide this won’t work for the firm. I’d be betting that the value I bring to the company would be worth it to them to keep me around on my terms – something I’m not naïve enough to take for granted.

I know that I run the risk of not being able to find another position if and when I decide I want or need to go back to work. I feel like I’m looking right down the throat of this gift horse. For years, I convinced myself to suck it up, show up, and sock away the paychecks. But it’s getting harder and harder to do. Every soul-sucking meeting I sit through, every ridiculous request from a workplace prima donna, every snarky comment from the resident Dwight Schrute has me longing to say “sayonara suckers!”

And I can’t help thinking about what I might gain. I can finally try my hand at something I think I would love. I feel like it could be my true calling.

I don’t know exactly what this new chapter might look or feel like, or what it will become. I only know that it’s coming.

Have you ever been faced with a situation like this? How did you make your decision? How did it turn out? I’m interested to hear your take.

As a thank you for reading this exceptionally long post, I’ll leave you with this little bit of nostalgia from my college years. This goes out to all the other goody-two-shoes out there!