Terra L. Fletcher

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Terra’s Story and a Peek into “Flex the Freelance”

Terra’s first website logo and image.

Enjoy this sample, the first chapter of Terra’s newly released book, Flex the Freelance: An Unconventional Guide to Quit Your Day Job.”

The Terra L. Fletcher Story

“It’s important to embrace some element of uncertainty, in order to truly experience wonder.”

– Chris Burkard, Photographer[i]

Do you hate your job? Do you dread going to work? Do you spend eight hours each day trying to convince yourself that if you’re paying the bills, your current job is good enough?

Are you punching the clock for someone else and miserable doing it? Sure, you try to focus on the good. You try to be nice to people and even smile. But at the end of the workday, at the end of each week, you’re emotionally drained and unfulfilled. Your work doesn’t align with your strengths, and the company’s values don’t mesh with your own.

Maybe you’ve drifted so far from your path you need to make a complete 180. Something has to give before you lose it and break down. That was me. I was on edge, and my boss always wanted more. My boss would ask, “Can you work extra hours this week?” The next week he’d ask the same.

It was October 8, 2009. I got up, closed the door to my office, and sat back down. I did what any self-respecting 20-something would do. I called my mom.

“Mom, I’m done. I just can’t do this anymore. I have to quit.”

I was good at my job. But I’d look out the window and wonder, “How in the world did I end up here?”

In high school, I didn’t know what I wanted to be “when I grew up.” Except for a writer. I always wanted to write. When I was a preteen, I scribbled poetry on scraps of paper and filled notebooks with free verse. In my late teens, I realized how difficult it was to make money writing poetry.

I wasn’t likely to make the New York Times bestseller list. And I’m a perfect or nothing kind of girl. If I weren’t a bestseller, I wouldn’t sell at all. Upon graduating from high school, I worked. I told school counselors, Grandma, and other concerned adults that I didn’t know what I wanted to do when I grew up. I’d snidely remark that my life plan was to marry a rich man. (Grandma thought this was a superb idea. “It’s just as easy to fall in love with a rich man as it is a poor one.”) But I was stubbornly independent and knew that trophy-wife wasn’t the route for me.

The truth is, I had always worked. Serial entrepreneurs raised me. I worked in restaurants and my dad’s bar. In the summer, I cleaned cottages. I volunteered. I worked at a nursing home.

My parents had a business I could always fall back on. It was a service company that I knew inside out. It grew up with me. I tried my hand at practically every aspect of the business. I didn’t realize yet, however, how entrepreneurship had gotten into my blood. Whether it was DNA or osmosis, it was there, deep. I didn’t know I needed to be an entrepreneur. I didn’t realize it was essential to me living my best life. Meanwhile, I thought I was just having a good time trying to figure out what it meant to be an adult.

I met a guy with a great sense of humor and three junk cars. We started dating after I graduated. We were married when I was 19.

Eventually, I went back to work for my parents. I managed other office employees, exhibited at tradeshows, and answered almost any question about having your chimney cleaned. (I could quote the National Fire Protection Agency’s code 211 in answer to, “How often should you have your chimney cleaned?”)

Like most employees of small businesses, I wore many hats. I instituted customer retention programs, designed ads, and built the company’s first website. Then one day, my parents called an all-team meeting and announced they had sold the business. It would be merging with another company.

I didn’t realize how attached I was. The company was born and raised alongside me. It was supposed to always be there as an employment option, my backup plan. My backup was gone without warning.

I wallowed in self-pity for a while, but the man I married wasn’t rich (sorry, Grandma), so I went job hunting. Soon, I got a “real job.” I was an optimistic 21-year-old with a fresh perspective and willingness to learn.

I started entering daily production numbers for an interior door and wood flooring company. I dabbled in customer service and marketing. I did my time answering phones. I filled-in on the production line, sanding doors, and became the resident Excel expert. If you needed a sales graph for the last five years sorted by state and wood specie and profit margin and color-coded to match the salesperson’s hair color – yeah, that was me. Eventually, I wound up as a cost accountant. I could tell you the standard labor and overhead rate for a square foot of finished flooring. I set the Kanban quantities for work-in-process parts (a LEAN manufacturing technique that helps supply just the right inventory to maximize value and minimize bottlenecks or delays). Basically, I did a lot of math.

But what was I doing in accounting? I’m a writer, a storyteller. This was the little girl who mentally scrambled words on cereal boxes and billboards – for fun! The little girl who would read the ingredients on shampoo bottles and memorize how to spell iodopropynyl, isothiazolinone, and sodium benzoate.

Always below the surface was that entrepreneurial drive bubbling, simmering.

In September 2007, I submitted a few articles to publishers. I sold five of the ten pieces I wrote in the first two months. I thought, “Maybe I can make money writing.” My freelance journey began. Selling what I wrote was a thrill! Even if it wasn’t enough to pay the bills yet.

In February 2008, I found out I was pregnant. I secured a ten-month writing contract to journal my pregnancy. It was fabulous! I was getting paid to do work I love! I couldn’t have been happier to get this gig. I would have journaled my pregnancy regardless, but now I was getting paid!?! My editor was great. I learned so much about writing online. The timing was impeccable; mommy bloggers were just becoming relevant. In June 2008, I started my first website, fletcherfreelance.com.

In October 2008, my husband and I welcomed a beautiful baby boy into our lives. I had been freelancing for a year already. I wanted so badly to work solely from home, to be there for my son. For a while, I thought I could, but the economy changed during the Great Recession, and no one was hiring freelance article writers anymore. I had to stay at my unfulfilling day job in accounting.

I feel like I must tell you that, of course, there is nothing wrong with accounting. It’s just not for me; I’m not a numbers person. I was pushed into a mold I didn’t create. I didn’t fight it either. I started in a part-time data entry position to pay the bills; five years later, I was still there. It wasn’t all bad; my BFF worked there. But I was dreadfully unhappy. It wasn’t just the job, but the job was changeable.

I had drifted far from where I wanted to be. All the pressure piled up, and I was suffocating. Under the weight of one too many excel charts, this camel’s back was broken. I reached that point, that place in time, crossed that line, hit that wall, STOPPED. That was it. I was done!

It was October 8, 2009. I closed the door to my office, sat down, and called my mom. She told me about the scores of people she knew who kept their side job for decades and never quit their day job. She told me the best advice I ever heard. (She always does.)

“Get out a calendar,” mom said. “Pick a day. Mark the day you’re going to quit. It doesn’t matter what day it is, just pick it! Put a big X on it. Now, work backward. What is the last thing you need to be able to do before you quit? And just before that?”

It sounds simple. It is. (I didn’t say it was easy.) She was right. See yourself at your end goal and plan backward. I set the date, April 14, 2010. That day I’d turn in my two-week notice. I knew how much money I needed to make and the cushion I wanted in savings. From that phone conversation onward, I worked harder than ever.

That month I joined the local Chamber of Commerce. In November, I joined the local writers’ group. In December, I joined the statewide writers’ group. I was attending meetings, networking events, and writing.

Thursday, December 3, 2009, I left work at my usual time. I had been looking for alternative employment, hoping to reduce my day job hours until I could make it freelancing. That afternoon I took a two-hour test as part of a job interview. Of course, phones weren’t allowed during the exam.

I missed a call from Gina, my best friend and coworker. She asked why I wasn’t at the mandatory meeting that afternoon. I asked, “What meeting?” She suggested I call my boss.

My boss told me the plant had gone into receivership (a fancy word that meant I was out of a job). He told me to come in the next morning.

I took my sweet time getting to work the next day. My boss gave me the official letter and asked me to help him with a few final reports. I packed up my personal belongings, ran off a few copies of my resume, and gave everyone my freelance business card.

It was snowing and windy; my mind was in a fog. I gave the company five years. I wouldn’t miss the lonnng physical inventories. I wouldn’t miss my car being covered with a fine layer of sawdust. I trudged through the snow to my car with my box of effects. Now what?

I drove by the company’s other plant to see who was still there. As I approached, I saw a TV van. I hesitated. I summoned all my boldness. I pulled over. I got on TV! I spoke positively of my former employer and put in a shameless plug for my fledgling writing business.

I had hoped to storm the boss’s office in four months with my two-week notice. I imagined what it would be like to quit my day job, how it would smell, taste, and feel. It was to be executed on my terms.

Instead, I felt executed. There was no pomp or circumstance. No great feeling of liberation. Just cold snow blowing on my face, doubt, and fear. Instead of symbolic leap taking, I was pushed. There was no press release, no going away party, no well-wishers, and no investors.

It was just me, alone, with a pen and a little more time.

I knew what I had to do. I knew business. I knew writing. I met with college counselors, a financial advisor, and my accountant. Despite my insecurities, I knew. I had to be an entrepreneur.

Searching for my niche, I dug deep to create a business that would utilize my unique skills, interests, and talents.

Recognizing the need for local businesses to have quality advertising and website content, Fletcher Freelance gained traction. I was committed to helping small and mid-size companies succeed by offering marketing, branding, and website content.

I had plenty of hard days, weeks, months. In 2010, I only made $9400. There were times I only got four or five hours of sleep each night. There were times when I wanted to sell my two-year-old to the zoo.

But then I remembered how out of place I felt before, how unfulfilled I was in all my other jobs, and how much I hated taking my son to daycare. My son and I would go to the park and see four adults to 100 children. And I remembered why I was doing this. Not just because I wanted to write, but because I wanted more time with my son. I tried to teach him by example the importance of keeping work in its place. My job had overrun me. I wanted to show him how to find more happiness at work by aligning our values with our careers. I wanted to show him that he was more important than my job. I wanted to spend more time with him.

Today, I work with entrepreneurs who base their business on a mission and vision they believe in. I work with people who do what they do because they want to and because it’s in their blood. Writing and communication aren’t just my jobs; they are my obsessions. I’ve never been happier.

I love my business. I love the psychology of marketing, the healing power of teaching communication, the ridiculous pace of social media, and the complexity of search engine optimization. I want to get inside your head and touch all the areas. I’m enthusiastic. I’m happy with my work and willing to tell anyone who will listen.

The speaking side of my business came by chance. The local chamber of commerce and tech schools asked me to speak, and I was broke, so I had to say yes.

I discovered that I enjoy teaching. I love the way someone’s eyes light up when they’ve had an epiphany. I don’t want people to learn the hard way, the way I did. I get to help people carve their career trajectory, communicate more effectively, and sell more.

When I speak, I learn because I listen. I share the absolute best golden nuggets I’ve gathered thus far, and people, in turn, share with me their finest gems.

I make people cry because I touch them deeply. I help them uncover a truth. Show them a profound perspective of their communication style. They understand how or why someone in their life communicates the way they do.

Sometimes, I give my audience the confidence boost and the motivation to ask for and get what they want. I help them believe they are worth it.

With my help, you’ll flex the freelance even faster than I did. You’ll find greater happiness, make more money, and enjoy more time with the people who are most important to you.

Work is not the enemy. Money is not the enemy. If you’re flexible and willing to freelance, it is possible to live the life you want. Stop staring out the window, daydreaming. Get your favorite mug, fill it with coffee or tea. Get a pen. Find a quiet place where you can be uninterrupted. Together we are going to flex the freelance and change your life. But first, you must be willing to fail.


[i] Reader’s Digest, 04-2018. “World Of Wonder”. P.50.

Terra L. Fletcher
Terra L. Fletcher is the marketing speaker, author, and Fractional CMO who talks about communication, branding, and marketing (everything from thought leadership to social media management, personal branding, and marketing for talent attraction). She is the founder of Fletcher Consulting and the author of three books, including "Flex Your Communication: 47 Tips for Every Day Success at Work," "Flex the Freelance: An Unconventional Guide to Quit Your Day Job," and the soon-to-be-released “Flex Your Marketing.” As a business builder since 2007, Terra’s strategies have benefited individuals, nonprofits, and public and private companies. When she’s not busy speaking or writing, you can find Terra painting, kayaking, or studying ads.
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