Almost exactly one year ago, I was boarding an airplane for a warm, tropical destination. Although I’d been a part-time freelancer for a couple of years, I had finally gotten the cahones to quit my day job and begin life as a full time self employed freelancer. My destination was Orlando, Florida for my first fully paid travel gig that involved a week of shooting at the University of Central Florida. It was an awesome trip that was followed by another week long adventure to Las Vegas where I appropriately had my spiritual rebirth of sorts via ayahuasca. At the time, I was nervous as hell to be for the first time without the safety net of being a full time student or full time employee. I had no idea if my third attempt at being self employed would work out this time. I figured I’d aim to make it at least a year before I tucked my tail between my legs and settled for another corporate job.

Nearly a full year later, I am back in a tropical paradise, this time in my childhood home of Hawaii, once again on a fully paid travel photography gig. It seems like an appropriate one year celebration, given that the whole year has been opening doors to opportunities that I never thought possible. I’ve traveled for a total of 4 months out of a full year, negotiated photography business with huge corporate clients on my own, generated more income than I’ve had since my corporate days, and (my biggest success in my book) was paid to travel and take photos on more than one occasion. I’ve also created more business opportunities than I can possibly tend to on my own, which has me excited for business expansion plans that are well under way. It’s been one hell of a ride, and I can’t wait to see what’s coming up in year two. Here are some of the key things that I’ve learned in my first year of living my dream.

Have clearly defined goals, and work towards them constantly.

I never had it in my mind to be self employed, but what drove me down that path was the realization at age 21 that living a corporate life for the next 20+ years just wouldn’t do. At the time, I devoured tons of books and blogs, marveling at the likes of Where Is Jenny?, Chris Guillebeau, Nomadic Matt, Tim Ferriss, and Sean Ogle, intrigued by the ideas of location independence and becoming a digital nomad. I remember that moment at age 22 when I made it my life goal to become one of those location independent digital nomads that I worshipped. My goal for this first year was to spend a whole year traveling as much as humanly possible. The outcome of sticking to that goal looked a little something like this:

Travels from one year as a freelancing digital nomad

July 2012: Glacier National Park, Montana

August 2012: San Francisco/Outside Lands Music Festival

September 2012: Orlando, Florida

October 2012: Las Vegas, Nevada

November 2012: Belize

December 2012: Guatemala

January 2013: Puerto Vallarta, Mexico

February 2013: Vancouver, B.C.

March 2013: Austin, Texas/SXSW 2013

May 2013: Oahu and Big Island, Hawaii

June 2013: Alaska cruise

July 2013: Oregon coast

It took 4 attempts at starting a career in corporate finance, several years of hobby blogging and photographing, and 2 failed attempts at starting my own business to finally be in a position to make the above itinerary possible, all while generating income on my own. But considering the fact that I’m still a few years shy of turning 30, I consider it a sign of success to finally have a self-created job and a business I feel confident and secure in.

Learn to Live with Less.

Taking dive from a full time corporate employee to a self employed person means the chance of a huge financial loss. Actually, it’s not just a chance, it’s a reality. To prepare for a decrease in pay, it’s essential to do a financial evaluation of how much you actually need to survive. It’s a question of how much is enough, which I think is nicely defined by Leo Bautista as “enough means having enough to live, and enough to be happy, and enough to thrive.” For me, this has always meant having a roof over my head, food in my belly, tools for creativity, and the means to travel.

Several months before I was contemplating leaving my full time job to strike it out on my own, I did an honest budget assessment of how much I would need to make every month to have “enough.” I tried out my minimalist lifestyle for several weeks, making budget adjustments along the way. In the end, my monthly monetary needs were strikingly small, and I knew based on further calculations that my freelance efforts could generate enough cash flow. A year later, I still refer back to this budget during times when my monthly income seems low. It’s a comfort to know that even at the lowest of the lows, I’ll have enough to get by.

Working for Yourself Doesn’t Mean You Work Less.

No matter what my occupation, either as a student, a McDonalds employee, or a corporate slave, I was always known for being a little too committed to my job. Considering that my job today is my own company, I’m lucky to be a natural workaholic. If I’m not careful, I’ll go 12 hours straight working on my computer, post processing photos, going over invoices and budgets, updating blogs, following up on leads and emails, etc. There’s no shortage of work to do when you’re a one person team.

One of the toughest realizations is that when you’re a one person team, there’s no such thing as vacation. You’re your own backup, meaning that those days you want to take a vacation doesn’t mean you can neglect your day-to-day work responsibilities. There’s no one to cover for you but you. As a result, I’ve found myself working around the clock weeks before a planned vacation so that I could take a week off of work. Even then, it’s tough to not check on emails in the event that an emergency pops up. Repeat: You cover your own butt in this game, there’s no one else to fill in for lost opportunities or neglected responsibilities.

Embrace Change and Variety.

During my attempt at establishing a 9-5 career, I was notorious for having my 1 year anniversary coincide with me handing in my 2 weeks notice. I couldn’t stand the idea of staying at a job or even an apartment for longer than a year. I embraced constant and extreme change, and I still do today. While this lifestyle preference didn’t suit me well in the 9-5 world, it turns out that my love for change is perfect for a freelancing lifestyle. I wear so many hats during the day that my resume could be a mile long. Luckily, I truly do enjoy pretty much all aspects of running a business (yes, even the book keeping and accounting!).

On that note, I’ve also learned that being diverse in my services and skills has also been an asset. Take this past month of September as an example: I’ve photographed everything from a wedding, music festival, concerts, real estate, charity dinners, shopping events, fashion runway shows, head shots, and even more random things I can’t remember. Yes, it’s good to become an expert in one field of photography, but I also think it’s invaluable to be versatile and tackle a variety of photo-related projects.

Expect the unexpected.

Despite all the planning and preparation you may do for becoming self-employed, it’s inevitable that some things will catch you by surprise. In my case, this happened in several specific incidences. Within the first month of becoming self employed, I realized 2 harsh realities. The first was the fact that I’d only be paid once a month, if at all. Gone are the 2 set days a month when you have an expected amount of money direct deposited into your account, or a paycheck awaiting collection. Most freelance clients will only pay once a month, or on their own billing cycle…if they bother to pay at all. The second reality was the extreme seasonality of my business. I was unlucky to decide to quit my day job right when my business season was peaking, only to find myself in the dead of winter a few months later, with hardly any jobs or payments rolling in. Now I know that winter is a time for escape and rest, not thriving off of business. My final unexpected moment came in the form of appendicitis, my first major medical incident that just had to happen when I had no health insurance of any kind. Luckily, that’s one adventure I should never have to repeat.

Set Boundaries for Yourself.

As I learned while reading entrepreneurial blogs, there’s a huge tendency for people working in their field  of passion to blur the lines between work and pleasure. Even while being aware of this happening, I admit that this continues to happen even a year after being self employed. Part of the problem is the only schedule you’re on is the one you make for yourself, which means that if you’re not careful, you can work 24 hours a day, 7 days a week. I’ve been guilty of doing this, sometimes out of necessity, and sometimes out of pure passion for what I’m doing. Either way, it’s unhealthy, and it’s important to set aside time for work and play. If you don’t, you’re bound to do too much of one over the other.

Remember to Put Your Loved Ones First.

I was quick to realize that many others did not understand my drive for working around the clock, especially those with traditional work schedules. As an example, one of my huge personal perks for working my own schedule was being able to revert back to my preferred night owl tendencies of working until the sun came up, and sleeping in til noon. While this would work for my clients, it wouldn’t work for my boyfriend and many of my friends. As a result, I’ve learned to make compromises, such as waking up earlier in the day and setting aside time in the evening when work is put aside.

Stay foolish, stay hungry. 

I was never much of a goal-setter until I started realizing just how motivational they are for businesses. I set goals on a regular basis–everything from a fixed income expectation to X amount of website hits I want every week–and I evaluate my progress constantly. Microsoft Excel and Google Analytics are my best friends. Not only is it inspirational to set goals, but they also show you where you might be falling short, offering room for improvement.

Another way that I stay motivated is to dedicate at least an hour a day to pure learning. I’ve found it best to enforce this by pledging to not do any work while eating. This usually entails drinking coffee and eating breakfast while scanning news headlines and setting up cool articles to go out on Buffer, eating lunch while reading photo blogs or watching blogging/photo tutorials, and eating dinner while enjoying a good conversation with friends or watching a TED Talk.

So…What’s Next?

As I mentioned earlier, I have serious ADD when it comes to holding the same job for longer than a year. This will make year number two of my current endeavor interesting, but not necessarily in a bad way, since I have a pretty clear picture of where I want to head. By relying on myself and only myself to generate income, I’ve become more self aware than ever. I know without a doubt what my strengths and weaknesses are. In a nutshell, I feel I’m better suited for a larger team environment. It’s not just because I’ve kind of been going crazy without the company of coworkers (you won’t realize how much you miss them until you don’t have them anymore), but a full year of doing largely one-off jobs has reminded me of what it means to have a larger objective to work towards. This next year will be about building more on my other business, Gemini Connect, which has the means and intent to become a full-fledged creative agency. I love the idea of bringing a bunch of creative, determined, business-minded individuals together to build bigger projects that we wouldn’t be able to achieve on our own. This is something I passionately believe in, and I can’t wait to push it along further. Stay tuned for how that all turns out 😉