Why I Quit My Job and Became an Entrepreneur

Overcoming Self-Doubt and Frustration to Follow My Dreams

I quit my Director of Marketing job earlier this year.

After five years, I felt it was time to move on. It was a job I’d loved ferociously at the beginning, but over the past couple years the joy of it faded. I felt bored, frustrated, and melancholic in my career.

I told myself to suck it up and get out of the funk I was in, but after a year of feeling that way I knew it wasn’t a funk. Still, I couldn’t figure out why I wanted to escape my cubicle so bad.

I was even angry with myself.

I was the Director of Marketing in a role that oversaw most aspects of marketing, social media, and even content (writing had always remained my biggest love) for a travel company. It was what I had always wanted. What I cried myself to sleep over in my early twenties because I wasn’t on the path to that type of career yet, and I wanted it so bad. Then in my mid to late twenties, it happened. I got what I thought was my dream job. For awhile I was insanely happy.

I was one of those annoying people who always talked about how much I loved my job and that I was excited for Mondays.

Then, things changed. There were some internal factors with the job that started to frustrate me, but the main problem was thatI couldn’t stand someone else being in charge of my time.

This was also the case when I started out in the real world after college when dreams of travel and entrepreneurship were all that I thought would make me happy. I thought I’d squashed those (unrealistic and irresponsible so I thought) dreams. But they came slinking back, ready to hit just when I thought I’d gotten my life pretty comfortable and ideal. And once that urge was back, I couldn’t get it to go away, no matter how hard I tried to convince myself otherwise.

There’s a recession. You work in the travel industry and get four weeks vacation a year with huge travel discounts – you know how many people would love to have that? You have a team of 12 people under you, you don’t have to do any grunt work anymore – isn’t that what everyone wants? You have a job, period – what’s wrong with you?

I was so mad at myself for feeling this way, and I was in limbo. I halfheartedly started this blog, but I couldn’t see a way out. I didn’t want to leave the travel industry, but there weren’t many marketing travel jobs in southern California and moving from San Diego wasn’t an option at the time. I missed writing, but everyone always said it’s impossible to make a career out of writing. I’d love to do freelance marketing, but how would I ever get any clients? I’d negotiated myself up to a decent salary in the past few years at my job – did I really want to go back to worrying about every dollar I spent?

So many questions. I was stuck.

And then I went to TBEX. And everything changed.

At the TBEX Keystone travel blogger and media conference I realized maybe I could make things happen. Maybe it was ok that I wanted a change. I prepared and did my research and got a couple regular (paid!) writing jobs out of it. I listened closely to how other people made it work – this whole balancing a life of travel with work, and more often than not, turning travel into work. I took notes from all the speakers and was particularly intrigued by Chris from C Around the World, who talked about how she balanced a freelance writing business with her travel blog. Though I was pretty convinced at that point that my freelancing would need to be some marketing to pay the bills, the way she described how she ran her business excited me and I felt it gave me some stepping stones to being serious about starting a freelance business.

I got back full of ideas and ambition. I knew I couldn’t quit my job yet and I didn’t know the end date, but I knew I was no longer stuck.

It took me another few months to get marketing clients (network, network, network – and have a web presence) and I began writing more on my blog. For awhile, I balanced all three, working until the early hours of the morning and dragging myself out of bed a few hours later to get into the office of my “day job” as I began referring to it. Then, a fellow travel blogger who I had a lot of respect for, approached me regarding a business idea and partnership. I was sold and knew then that it was time for something to give – namely, my “day job”. It was time to officially start on the entrepreneurship road. Nothing was a guarantee, there was no steady paycheck, but that excited me. It was time to pursue my true calling – being a writer and being a location-independent entrepreneur.

The location-independent part is important to me. If I want to work from my family’s house in Montana or from a café in Paris, I want to have that flexibility. Since quitting my job, I’ve been to Utah, Boston, Montana, Mexico, Nantucket, and San Francisco. If I’m visiting people or traveling with others, I make it clear before departing that I’ll be working every day. By managing that expectation, working on the road is not a problem. Most people in my life are ambitious so they’re busy working, too, or they accommodate plans while I’m in town around my work schedule.

This type of working would have been nearly impossible when I had my desk job – it’s just not allowed in most office environments. What’s great is I still get to do what I love. Though writing will always be a passion of mine, I love marketing, too. It’s interesting and always evolving. And now that I’m able to have the time to dedicate to both, I’m thrilled. It was a long, sometimes scary road to get to this point, but I knew I’d always regret it if I didn’t try.

So, after careful planning of what I was going to say, I walked into my boss’ office 4 months ago and put in my two weeks notice. It was one of the scariest and best days of my life.

Later that night my husband took me out to my favorite wine bar and we toasted to my new beginnings – really our new beginnings. He no longer had to listen to me whine about my job and there was no way I could have taken this leap of faith into entrepreneurship without his encouragement, support, and tolerance of me typing away on my laptop until the wee hours of the morning every night.

I’m excited to see where things go with the writing I’m doing through One Day in a City and the other publications I write for. Travelers revel the unknown and exploring, and so far as an entrepreneur I’m reveling that each day could bring something new and exciting for my career. It’s turning out to be more exciting than scary (though I assure you I still have some freak-out days) not knowing what tomorrow brings.

I definitely look at entrepreneurship as a career – one that has me busier than ever, so will still be posting regular articles on this blog about how to balance a career with travel. In my case, to balance it, I had to find something location-independent, but there are many ways to find the right mix for you to have both the career you desire and the traveling you’re itching to do.

 

If there are any things in particular you’d like to know about balancing your career with travel or starting a business or getting into freelance, or have any other questions, please leave them in the comments. I’d be happy to answer them.