This article is written by Location Rebel member Jennifer Winter. Since meeting Jenn a couple months ago I could not be more impressed with the strides she’s making towards building a business and taking control of her life. Check out more of her writing at Fearless Jenn.

Until about a month ago, I’d never truly experienced fear. Or, I if I did, I didn’t recognize it.

I fell into financial services over 13 years ago, and although I’ve never really liked it, I did pretty well, so it was easy to misinterpret my fear of branching out as simply my gut telling me I should stay put. I felt safe and comfortable right where I was, so why mess with a good thing, right?

Yet I would often find myself stuck on a continuous loop of daydreaming about a sabbatical (which I knew my former employers would never have allowed) and this nagging feeling that I was wimping out on my own future.

So, I did what any scardey cat would do – I hid.

I poured myself into my work, distracted myself with relationships I knew wouldn’t work, and probably drank more than I should’ve. I was avoiding the inevitable.

Happiness eluded me and despite my best efforts, I just couldn’t love my job, or my life. I self-diagnosed myself as depressed, and eventually spent a truckload of money on therapy, desperately hoping someone else could fix me. Clearly I didn’t think I was up to the job.

Misery persisted, and after draining my entire savings on attempts to “quick-fix” the rut I was in, I had to admit my approach was flawed. I needed to try something else.

During one of many wine and tear-soaked evenings after work, I think I snapped a little. Before, just the thought trying something different (e.g. NOT finance) scared the hell out of me, so I confined those dangerous thoughts to fantasy and daydreaming, never allowing those ideas to fully marinate in the ‘real’ world. But that night, I said fuck it, and let myself just imagine starting over. What started out as a drunken pity-party, evolved into a simple realization that eventually changed my life.

I gave myself permission to actively plot a future that was completely uncertain, and allowed my thoughts to wander freely.

Thinking quickly led to writing, and lots, and lots of fantastic daydreaming – this time allowing those dreams to mingle in my real world.

Then, I was introduced to Sean and the concept of becoming location independent. A bell went off in my head and I literally felt illuminated. I knew I was on the right track. Suddenly the possibilities seemed endless. To say I was excited (and happy) doesn’t quite cut it.

Well, fear didn’t like my new-found confidence and ambition, and quickly stepped in to slap me into submission. One minute I was imagining myself working from a laptop, eavesdropping on conversations in languages I didn’t understand, and the next, I was plagued with dread.

I thought to myself; I can’t afford this, I have so much debt. What will I do with my stuff? My house, my car…my cat? I looked around the living room of my cozy little house and I actually felt guilty for even thinking about leaving it behind. My fantasies of being my own boss and letting my true self develop, were subverted by feelings of guilt, irresponsibility and selfishness.

In an instant, I caved to my fears and resigned myself to the fact I was forever stuck in finance. What immediately followed was a deep sorrow for the loss of my dream.

Then, I just got pissed off. How could I give up on this so easily? Why was this so difficult?

Dreaming about a change is one thing, but doing something about it guaranteed I’d have to stare down my deepest, darkest fears and probably a few I never even knew I had. But the pain of grieving the loss of my potential new life was unbearable, and I knew I had to figure this out. And then it hit me.

I needed to learn to embrace fear – not try to outrun it.

With my newfound resolve I committed to making a change, no matter how much that voice in my head resisted. So, I continued to write, joined the Location Rebel community and started a blog. I let the fear come and go while I trudged forward, and slowly I started to notice I was changing. That’s when I knew I was ready for the next step.

It was time to hand in my resignation.
I wasn’t prepared, I didn’t have a plan and I had no idea if I would be able to support myself. But man, let me tell you did it feel fucking amazing to tell my boss I was leaving to “pursue my creative interests”. The look on his face will stay with me for a while, and despite his barrage of questions and unsolicited advice on the matter, I was drunk with happiness as I left the office that day. One of the best days of my life.

Until I got home.

I should’ve known the high wouldn’t last. It took just minutes after walking through my front door before I started to suffocate with fear. I collapsed on the couch, notebook and pen in my shaking hand. I was terrified, but if I really wanted to be a writer, I should be able to translate that fear into something moving and raw, right? Yeah! Take that fear!

Ahem. Well over an hour later I had scribbled just one lousy sentence on the page. All these emotions were flying around in my head, and I couldn’t even name them, let alone write about them. Aaaannd the fear was back. I was overcome with doubt as a tidal wave of horror knocked me down and I questioned my boldness.

The usual topics raced through my head and I cursed myself for being so impulsive. I felt lost and completely alone. And, once again I mourned the passing of my ambitions as I allowed fear to take hold and throttle out every bit of hope I had left.

I cried, I drank, and then I cried some more. Mercifully, I fell asleep as I dreaded going in to work the next day, feeling sick that I had put myself in this position.

But when my alarm jarred me awake at 4:30 am, something had changed. My situation didn’t seem nearly as bad in the light of day and my confidence and excitement had resurrected. I learned my first lesson about fear that morning:

1. Fear is temporary

That may seem like a simple observation, but when you’re paralyzed by the stuff, knowing it will end can be extremely comforting.

I got up, wrote a few pages, then dragged myself to work. I wasn’t looking forward to going in after I had resigned, but I was giddy with excitement over my revived creative energy, and eagerly awaited the return of my writing abilities to come bounding back (think rainbows and kittens and cotton candy) upon settling in my cube for the day.
After about eight hours at my desk and no rainbows in sight, I started to get worried. Again. In marched fear, and with it, my second lesson:

**2. Fear is f@#%*$ persistent**

We all know fear is just a part of everyday life, but I don’t think I really gave it credit for how damned relentless it could be. Every single day from the moment I quit to right this moment, fear has become a visceral part of my daily routine. I expected to have a few minor freak-outs along the way, but I was completely unprepared to battle this on a daily, sometimes hourly basis.

But, after about a week or so, I became accustomed to my daily relapses and felt mostly prepared for them. I already knew lessons 1 and 2, so I got a little cocky. I thought I was winning the war.

Whoops.

It’s as if fear can smell the confidence in the air. Just as soon as I started to believe I was beating this, my fears took the opportunity to show me what’s up.

One morning while furiously writing at my desk, my boss called me into his office. My heart stopped. I immediately assumed I was being called out for working on personal projects on company time. Imagine my surprise when instead, he asked me to reconsider my resignation! He lathered on the praise, making me feel important and valued. He knew exactly what to say. Flattering, right? Actually, no, not so much. Enter my third lesson:

3. Fear is a sneaky mofo – it can disguise itself as opportunity or choice

Now, in addition to the fears I had been taming so far, I was forced to completely re-visit a decision I had already struggled to make. This is where fear got really creative with me. Instead of recognizing this as an attempt to serve my boss’ own agenda, I translated it into a compliment and saw his offer as an opportunity.

Once again, blank pages, wine and massive freak-outs ensued. By masquerading as a new choice or opportunity, fear had worked its way back into my head in a whole new way. Although I knew I still wanted to quit, I was now faced with the disappointing glances and wild mood swings my boss would undoubtedly inflict upon me when I reiterated my resignation.

Sure enough, he wasn’t happy and proceeded to make my days even more miserable than they already were. One moment he’d be fine, and another he’d be yelling at me so loud the entire office could hear (apparently he had forgotten what a valuable asset I was only a few days before).

I would endure this game of “are you sure you want to quit?” with him FOUR more times (and counting), each time leaving me feeling suffocated and rendered helpless with fear and doubt.

But I’ve made it this far, and have no intention of backing down now.

The final lesson?