How Two Moves and a Major Career Change Led Me to Happiness and Financial Freedom


For as long as I can remember, I’ve always been incredibly risk-averse. I’m that person you can count on to always have a tissue, a bandaid, or medicine handy. I look up directions to a new destination even if I’m 99% sure of how to get there (and leave 15 minutes earlier than necessary). I always have a backup plan for my backup plan. You know, just in case.

In my mind, being risk-averse had always been a win-win. It provided me the luxury of never being late, never getting lost, never getting caught by surprise. Always armed with a plan of action.

Unfortunately, it also meant that I was inflexible and unwilling to pursue things that I couldn’t outfit with a safety net. As nice as it is to be prepared for everything, sometimes that prevented me from doing anything. Some things in life simply can’t be fully planned for. Sometimes you have to take a leap of faith and jump off the proverbial cliff.

And that’s how I found myself in a situation of being extremely dissatisfied with my career and struggling financially. And I do mean “found” myself in that situation – because I certainly wasn’t actively pushing myself into a productive direction. (Of course, I thought I was at the time.) Looking back, I realize was doing nothing but pursuing back-up plans before even giving myself a chance to chase my dreams.

So, at 25, I took a big risk. And then, at 28, I took another one. These crazy, scary, terrifying moments ended up being the catalysts driving me forward to the life I wanted in the first place – the life I was too scared to go for after college. This is the story of how two moves and a major career change led me to happiness and financial freedom.

Letting Financial Fear Dictate My Life

As my friends like to joke, I tend to be a walking contradiction. I’m the former ballet dancer who loves football, the wanderluster who hates long trips, someone who’s impatient, impulsive, and gregarious – while also being risk-averse, perfectionistic, and shy. None of these traits together make any sense, but alas, that’s me. While I can now appreciate the things that make me uniquely me, they caused me quite a bit of frustration growing up.

Most notably, my artistic and worry-wart side were always at odds – though the worry-wart side inevitably won most battles. And thus, I spend my life living in financial fear. In the right circumstances, fear isn’t such a bad thing, as it can lead to heightened awareness and preparation. But uncontrolled, fear is debilitating.

So when I graduated with a degree in English and couldn’t get a job as a reporter at the local newspaper or editor at the local publishing companies, I started working for a bank – simply because that was the job I could get. Now, why I was even looking for a job in my hometown is beyond me, considering I always dreamt of and planned on moving to New York. But I had a plan in mind. And that plan was that I should stay long enough to get “enough” experience in my field to move away.

The years went on and I got no closer to finding a job in my field. I also got no closer to financial freedom. Student loan payments and a meager hourly wage left me living paycheck to paycheck and feeling truly stuck. Finally, I got fed up with my job and my situation and…

…I obtained the worst job ever. I’m talking the worst. It was in admissions for a local art school and I thought it was going to be amazing. I envisioned myself ushering high school students to their dreams while finally earning enough money to start saving. That dream came crashing down to the ground when four people were fired on my first day – including the person who hired me – and I was handed a stack of papers with phone numbers to call.

Of course, I now understand that the school I thought was so great is actually a dreaded for-profit college and that admissions for those types of schools is nothing more than a sales position. Nonetheless, I took my daily call sheet and busted out the required 75 calls a day until a few months went by and I was able to save enough money to move away. Years later, I’m glad I went through such a tough position because I made friends that I’ll keep for life – both in my students and co-workers. But most importantly, it led me to the desperation necessary to finally go after my dreams.

Taking that First Leap

Though it took me just about forever to take a leap of faith, once I did I came across some very surprising realizations. While these realizations may not match everyone’s experiences, they make for some interesting lessons:

Once you decide to take a leap, things start happening quickly.

One day I was chugging along dreaming of New York and struggling financially. The next day, or so it seemed, I was packing my bags.

Something inside of me was just done. I was done struggling, done dreaming. And once I made that decision, there was no turning back.

Once you decide to take a leap, things which seemed impossible suddenly don’t anymore.

I always felt like New York was like a holy grail – an impossible dream that I just had to have. But how? It turns out the answer was pretty logical. Save money. Give away what you don’t need. Look for jobs and apartments on Craigslist and other websites. Buy a plane ticket.

That was it. That was my magic plan for achieving my big city dreams. In July I made the decision to go for it. By September I was living in New York. Not only was it my first time living out of state, it was my first time not living with my parents. And, in the end, it was so easy.

Once you get to the other side, you realize it wasn’t so hard afterall.

I’ll never forget that first day in New York: dragging my two suitcases and duffel bags up the six(!) flights of stairs to my new apartment. It was a typically hot and humid late summer day and I was exhausted. I sat on my bags on the floor and looked at my new room. I made it. I was finally there. And in the end, it really didn’t take that much to make it there. I broke through the imaginary walls I erected around the city and suddenly I was a New Yorker.

The leap can work – if you’re ready to hustle.

I didn’t rest long. For the next eleven days I sat day and night in my new room applying for jobs. I left no stone unturned. I applied for jobs at Starbucks, at retail stores, at corporations, and through recruiters. On the eleventh day I was called in for an interview and, before I even left the building, I had the job.

I wish I knew now exactly how many jobs I applied for, but all I can say is it was a lot. I made it my 12 hour a day job to apply for jobs – and it worked. My new gig wasn’t the job of my dreams, but it gave me enough money to live and a predictable schedule that allowed me to focus on my writing.

Even when the leap succeeds, things can go wrong.

I was excited when I got the job, but I didn’t get too comfortable. The risk-averse side of me still reared its ugly head (to the point at which I was physically nauseous every day for months). And, on the first day of my job, the economy verged on the brink of collapse. No sooner than I walked in the door, it looked like my company might go out of business. But we kept going and that job, while not the job of my dreams, was the job that helped me get out of credit card debt, led me to my favorite volunteering activity, and helped me pursue my dreams of living and writing in the city.

The cost of risk can lead to far greater gains.

The final lesson I learned through all of this was, although risk is scary and can cost a lot, it can also reap great rewards. The things that kept me from moving sooner were fear of not getting a job and wondering how I could possibly manage to pay New York City rent. However, once I got there and got a job, I earned more money than I ever had before.

The costs of the plane ticket and security deposit for the apartment were returned quickly by my new salary. Granted, I still wasn’t earning much (some of my friends wondered how I even survived on my pay), but it was a lot more than I was earning in my hometown, thus negating the risk of higher rent. I quickly realized that I could have been in a much better financial situation if I made the move years earlier. (Of course, hindsight is always 20-20.)

It’s also worth noting that I led an incredibly frugal lifestyle, which was another way to make sure my risks were calculated and not unbearable. I shared a bedroom with my (now) best friend for almost one year. I packed breakfast and lunch and cooked dinner. I went out but had a strict $20 only spending rule for each weekend night. As time went on and my debt went down, I was able to lightly upgrade my lifestyle, but frugality was and is always forefront in my mind.

Never Allowing Myself to Get Comfortable Again

After three and half years in New York, California started calling my name. It had always been on my bucket list to try living on both coasts and the lure of startups made me dream of a job in which I could have real impact every day. This time, however, I wasn’t going to let several years go by.

I talked to my boyfriend (now husband) about moving and, after a few months of convincing, he was on board. Again, we made the decision in December and were living in San Francisco by March. Again, I didn’t have a job before I went, but I did have several months worth of living expenses saved up. And, perhaps most surprisingly, again I was terrified. What I learned after my second move was…

…it never gets easier to take a big risk.

There were so many reasons not to go. I loved New York. I had a good job. I still had student loan debt to pay off and hadn’t started saving for retirement yet. But I knew it was something I just had to do. And thank goodness I did, because otherwise I wouldn’t be writing this today.

In fact, I probably wouldn’t be getting paid to write at all. Moving to California has given me an opportunity to finally achieve the job of my dreams – wrapping up my love of writing and helping people all in one. What seemed like a truly crazy thing to do ended up being one of the best decisions I ever made. For me, the only way I could do it was by taking this risk because, again, I’d gotten too comfortable.

Since then I vowed never to get too comfortable again. My job has taken me through many challenges, throwing me into responsibilities I never had before and with no guide book to help me. Through that I’ve grown tremendously – but most importantly I’ve learned to get comfortable with the uncomfortable. I’ve learned to adapt, to try new things, to be willing to try and fail versus not try at all.

The very actions which at first glance could have damaged my financial situation ended up helping me reach credit card debt freedom and get on a path to student loan debt freedom. These actions that could have so easily led to failure led to the life I always wanted. And I’m not going to stop here. Never again will I get comfortable. Never again will I stop growing and striving for my goals.

What about you? What would you do if you could do anything? Leave your response in the comments below! You never know, it could be the first action you take to help you take that leap!

Image Credit: Lotus Carroll

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  • Meena

    Great post. Although I haven’t achieved success in my new career yet, just steadily working towards it may be the hardest part. It’s easy to just stay at a “good enough” job. But I want to do more.

    • Shannon_ReadyForZero

      Absolutely, Meena! Sounds like you have the right attitude and, if you keep pushing forward, you’re sure to get where you want to go :). Keep us posted on how things go for you!

  • bookishheather

    This is a great post, Shannon—thanks for sharing your experience! I think that typically, one’s 20s are about discovering these type of things. I have a similar story…except I was in my 30s when I got my risk-taking year of adventure and career-building. : )

    • Shannon_ReadyForZero

      Thanks Heather! While it’s easier to do in our 20s, it’s never too late to take risks and keep pushing ourselves forward!

  • Joel NR Powell

    Great read! blessings to an even more successful journey.