The Ups and Downs of Being My Own Boss as a Professional Photographer

One of the most inspirational, challenging, momentous and, occasionally, disappointing years in my life occurred between May 2014 and May 2015.  Even though I was a sole proprietor and had owned my own small photography business for four and a half years, I was still working full-time for an employer in Seattle. It was the job I had when I started TIA International Photography in December 2009.

“Take This Job and Shove It…”

By May 2014, I had been with the same employer for approximately seven years and seven weeks.  During that time, I believe my role had persevered through five different infrastructure reorganizations. By the time I had finally decided to resign, I was submitting my notice to my seventh immediate supervisor.  That averages to a different supervisor each year during my tenure. Thinking back, I recall that I had had enough after the first six months (my boss was conniving, crafty, insecure, and untrustworthy), but I believed in the organization’s mission and didn’t know back in October 2007, when I was initially exasperated, that I would remain onboard for another turbulent six and a half years.  Starting my own business as a photographer mitigated a lot of the corporate politics that I dealt with during the day.  With my photography, I always had something to look forward to that brought intellectual stimulation and pleasure after hours or over the weekend.  Photography was my escape as well as my stress reliever.

What I did not expect was for TIA to be successful in the years following its registration with the City of Seattle as a small business on December 1, 2009. (I need to do something to commemorate TIA’s 10th anniversary in 2019)!  I honestly believed the business would fail after a year and I would resolve to pat myself on the back for giving entrepreneurship a shot.  That expectation couldn’t have been more incorrect.  In fact, by the time I had my first public gallery showcase in December 2011, many of my co-workers who I invited from my full-time job believed that my days of working “nine to five” were numbered as my photography would likely gain enough attention to do it full-time.  A few days after the gallery showcase, one co-worker took me aside and asked (paraphrased), “Tosin, does this mean you’re leaving us?  Your photography is so wonderful that I imagine it’s inevitable that you won’t be working with us for much longer.”

As it turned out, I stayed for several more years until the latest reorganization essentially demanded that I make a very serious decision about whether to continue my employment.  I had been saving my personal income from the day job and additional income from TIA’s success for many years.  In the back of mind, I had often wondered if I could run TIA without having the steady income from a daytime job.  Could TIA (a.k.a. “I”) survive as a freelancer over time?  This specific question had been on my mind for years, and whether I had the confidence to leave and find out.

At 1:01pm Pacific time on Friday, May 30, 2014, I determined it was time to test my hypothesis and let the long-awaited experiment commence.  After spending months weighing the pros against the cons, I quit the day job. An hour and a half later, I drove 80 miles (130km) north to privately and introspectively observe my self-implemented emancipation from having worked for multiple employers in six states and the District of Columbia for nearly two decades.

“In that One Moment in Time…”

Of course, May 30^th was a day of jubilation. I was skipping instead of walking.  I was singing along — and aloud! — with Janet, Whitney, Mariah, Tina, Diana, and all the other indelible divas who had songs featured on my myriad of iTunes playlists. I felt a combination of different emotions swirling rampantly within my psyche, ranging from exulting exuberance and jovial joy to restorative relief and illuminating liberation.

I was finally free.

Then came May 31^st. I was still free.  Nevertheless, the question that arose was precisely the one that occurs after a group of people struggle and strive so long to painstakingly achieve an objective and then — finally, suddenly, or miraculously — achieve it:

Now What?

Fortunately, I had contemplated all of this and already had a plan for what I wanted to do with TIA for the remainder of the year.  I had written a detailed business plan regarding how I wanted to market my services, how to increase my clientele, and how to sharpen my skills as a professional photographer.  I shared my plan with friends who I knew would give it a critical eye and provide feedback of the plan’s strengths and weaknesses.  The month of June was spent solely on how to garner more attention and business for TIA, starting with potential customers in Seattle.

With new freedom came new opportunities for self-improvement too.  I no longer needed an alarm clock to wake me up at a certain time if I did not wish to wake up at that time. (Bliss). I no longer possessed any dread within my body about the commute to the workplace or what or whom I would encounter at that workplace. (Bliss squared). I could make my own schedule and do all the things I never had time to do when I was under another company’s employ. (Bliss squared with a hazelnut latte and a chocolate doughnut).  

It dawned on me that I was my own boss, at last, and only had to be accountable to myself and my customers.

“Ooo-Oooh! Ooo-Oooh! Oooh! I’ve Got a New Attitude!”

Being in charge of my own affairs meant I could follow my own schedule instead of one dictated by someone else in which I had to comply.  I could spend longer hours to work out in the gym or at home.  I could go on longer bike rides around Seattle in the morning.  I recall losing almost 20 pounds after I quit my daytime job.  I was happy, healthy, in shape, and stress-free.   After my morning exercises, I would engage in different activities regarding my photography business.  On Monday mornings, I would plop down in my den and read about what’s trending in the photo industry and peruse articles in the latest editions of Photo District News or Outdoor Photographer that had previously been piling up on my coffee table.  On Tuesdays, I would read my textbooks and online articles regarding how to manage a small business.  On Wednesdays, I would spend time developing or revising my official website and engage with existing and potential contacts in all the social media networks.  I had time to do all of these things, which I never had had the time to do before.  It was incredibly liberating to say the very least.

That summer, I enrolled in two separate Photoshop courses in Seattle.  I had never been fully informed of the application’s major functions and I was determined to sharpen my editing and post-processing skills to improve my images and make them more appealing and marketable.  This was probably one of the best decisions that I had ever made while working for myself because I have consistently applied those same acquired skills that I learned back then to this day.  For example, I was not familiar with the process of layering images before I enrolled for my courses. I can honestly admit, now, that I don’t know how I managed to process photographs before obtaining more knowledge about Photoshop’s numerous and beneficial features.  As a result, I have frequently gone back to older portfolios and completely re-edited them based on the education I received from my Photoshop classes provided by Luminous Works and South Seattle College.  Today, I can clearly see the difference between my photography before and after Summer 2014. Below, you can see some examples of how I processed cityscapes before and after I took Photoshop courses. The difference may surprise you.

Alongside taking courses to improve my skills, there was also the marketing aspect of the business. Marketing my photography was a daily, perennial, nonstop effort that was both exhilarating and frustrating simultaneously throughout the year. (To be honest, marketing has always been stress-inducing since TIA’s inception). Because I was literally working for myself, I had the time and, fortunately, the resources to execute a few different means of letting potential customers know that I had this business and could offer my services to them. I created hundreds of flyers on card stock paper advertising TIA. I spent about $150 on stamps (yep, snail mail “Forever” stamps) and some more dollars on manila envelopes. One objective was to both mail and email the magazine publications, travel/tourism publications, and commerce bureaus for whom I believed my photography would be of value. This included publishers based locally in Seattle as well as many others in the USA, Canada, Europe, South America, and Southeast Asia. I knew that receiving responses would be a long shot, but I couldn’t allow that to be a deterrent to my goals. I was determined to inform the masses that TIA existed, and entering people’s mailboxes and inboxes was one means to achieve this. Below are a few of the flyers that were distributed during my marketing campaign.

I also compiled my best cityscapes and had them printed in professionally bounded photo books which would serve as my official printed portfolios. I did this because, occasionally, some potential customers and partners desire to see a photographer’s work in print instead of digitally via website or social media network. In fact, before I could host my second official gallery showcase in 2015, the curator at the venue specifically required that I submit my portfolios in print as a prerequisite to featuring my work. He didn’t accept website portfolios. The advantages of having printed portfolios are many, including the fact that you will always have them ready to present whenever they are requested. I used ZNO (previously Artisan State) to produce my printed portfolios: one for Seattle, a second one for American cities, and a third featuring international cities.

“Let Me Take You on an Escapade! Let’s Go!”

Quitting the nine-to-five back in 2014 also allowed me the leisure to give more attention to a separate, self-assigned photo challenge that I called “Project 2014 : 365”. This year-long endeavor involved capturing one photo each day of the year of any random subject matter (a far cry from the regular cityscapes to which I am accustomed) with the caveat of using the camera that was in my proximity and not necessarily the camera of my preference. I had done well before my resignation, but had much more time to be creative and less harried afterwards, and I loved it. When it was over, I had managed to succeed with a 99.7% score, having missed only one day out of the 365. (I had been on a return flight from Australia to America on the day that I missed). This project allowed me to photograph subject matters I would never have thought to photograph in the past. Compounded with my new photo-editing and post-processing skills, my project became a means for creative and industrious experimentation that I could apply to various subject matters in the future.

I believe the last decision I made with marketing TIA in 2014 turned out to be as significant as investing in my post-processing skills. This particular decision has significantly contributed to why I am still in business today, in 2019, on the cusp of my 10th anniversary. I wouldn’t have predicted it, but volunteering my services to an organization whose goals I admired or shared made a remarkable difference in the long term. That organization turned out to be the City of Seattle’s Parks & Recreation division. To be truthful, I will add the disclaimer that I volunteered my services to many local organizations, but Seattle Parks & Recreation (SP&R) actually took the time to respond. During the holiday season, SP&R hosts the annual “Christmas Ship Festival”, an event in collaboration with Argosy Cruises in which one of Argosy’s large cruise boats, containing a choir, sails among a parade of boats, decorated in multicolored holiday lights, to different parks that border water in the metropolitan Seattle region. At those parks, residents and visitors alike congregate and listen and/or sing Christmas carols along with the choir on the main cruise boat.

In response to my offer to volunteer my photographic services, SP&R tasked me with capturing a few of the Christmas Ship Festival events at different parks in addition to separate holiday activities taking place in downtown Seattle’s Westlake Park. I was happy to engage because this effort involved traveling around the city to places I either hadn’t visited before or wasn’t completely familiar. I got the benefit of getting to know my city of residence better, for which I always find value. It was also a tremendous chance to impress SP&R, which I was able to accomplish! SP&R loved the work I submitted for the 2014 holiday season. As a result, the City of Seattle Parks & Recreation department, alongside other city departments over time, has become my biggest client for paid photography assignments ever since, for which I am eternally grateful.

“Back to Life. Back to Reality…”

Up until this point, I have been cheerfully describing my year of liberation (and lots of fun) with my focus on boosting my small business. There were a lot of advantages and positive moments, but it would be folly and unrealistic to deny the disadvantages and what did not go well or as expected…and there were plenty of those moments too.

As far as the marketing campaign went, virtually none of the companies who I contacted responded. Even more disappointing was when the flyers I sent were returned because the address was out-of-date or completely incorrect. Many times, I would get my emails sent back to me for the same reasons. The phone never rang. I have had my own business landline number for TIA for nearly 10 years, and the people who use it most tend to be family members and friends. (Not that I’m complaining. I want them to be able to reach me when they need to, but they were not the intended “market” for this particular apparatus and mode of communication).

There were days when, after I had done everything on my schedule, I still felt unfulfilled, upset, or disheartened that things weren’t happening right away…when I wanted them to happen. After all, I was free to do photography and I was announcing to the world that I was free and available. That didn’t mean the world was ready for me or needed me at the time I was ready. During my time on this planet, this has proven to be a valuable lesson to me. Life is not linear by any means. This was a lesson I probably was unable to grasp previously because I had never witnessed it for myself, until 2014 when I wanted everything to come together simply because I was ready. When one says “the world doesn’t revolve around you”, that is an absolute fact, and this fact hit me very hard as the year progressed with the lack of response or attention, despite all my efforts to generate business. I advertised on Facebook, Twitter, Craiglist, online classifieds for newspapers serving New York, San Francisco, Los Angeles, Washington, Boston, Denver, Miami, Chicago, Las Vegas, and Vancouver. I tried to use a third-party service to connect me with photo buyers, which inevitably turned out to be a disaster and led to this article that I previously published on this blog.

On certain days, I remember binge-watching my favorite Japanese anime series for hours because I couldn’t think of what else I could do that day to market TIA to the masses. Binge-watching a series was fun on occasion, but it didn’t feel right because this byproduct of my liberation wasn’t related to what I expected to be doing — marketing my photography and providing services. Each episode of watching the masterfully written story (and hi-jinks) that is “Naruto” was time I wasn’t spending on my photography business.

More importantly, if I wasn’t being hired to provide services, that meant I wasn’t being compensated. My bank accounts weren’t seeing any new income. Going from being a full-time employee with a consistent bi-monthly income to working freelance and not knowing when or from where I would earn income became a bigger concern as the new year approached. I had been relying on all my savings and I didn’t want to completely deplete them, but that’s exactly what was happening, and this became increasingly disconcerting for me.

“The Policy of Truth”

Eventually, 2015 had arrived and I was still at a loss with acquiring new business for TIA. The volunteer work for Seattle Parks & Recreation had been enjoyable, but it was still volunteer work which compensated me with every fulfillment other than financial. I had no choice but to commence a new job search. I had taken the risk, and taken advantage of it wholeheartedly, but the bottom line was that the actual bottom line was disappearing.

I started a new nine-to-five in May 2015 with another employer. I will never forget the harrowing and sinking feeling I experienced on my first day when I first sat down in front of my assigned laptop in a cramped office space that I shared with two other people. It was over. Figuratively, it felt like a part of me had died. My freedom had concluded and I was now subject to the irritating insult and subtle subservience that came with many nine-to-five roles. It was a jarring sensation that made me rather unhappy. My saving grace was that Seattle Parks & Recreation had hired me for my first long-term assignment that I could do after-hours and during the weekends. Thankfully, history wasn’t completely repeating itself this time.

It’s essentially been this way ever since to today — working for an employer but doing photo assignments in the evenings, weekends, and occasional lunch hours. I’m not crazy about it, but this is my reality and my truth. I also need to be pragmatic because I have to pay rent in Seattle, which is another, separate debacle now that the Emerald City has officially entered the Top 5 list of America’s most expensive cities, featuring an extraordinarily exclusive club consisting of New York, San Francisco, and Honolulu prior to Seattle with D.C. rounding out the list.

Nevertheless, I can’t and I won’t give up my goal of letting TIA be my primary source of income in the future. I don’t regret taking the chance that I did back in May 2014, and I would do it all over again because I have learned so much from the experience. I’m glad I no longer have to ask myself the question,“What if I tried to go solo?”, because I know the answer. Furthermore, I loved being my own boss and being accountable only to myself. If I made a mistake, I was clearly to blame. If I scored a victory, I could wholly own the credit without deception or equivocation. There was no drama of dealing with other people’s baggage or insecure supervisors or gossiping coworkers whose primary goal was to climb a corporate ladder and appear prestigious while diminishing my contributions in the process. I truly don’t want that negative, counterproductive energy in my day to day affairs — it’s pitiful and petty — so I avoid it when I can identify it.

Being my own boss eliminated all that rubbish and stress for an entire year and made a profound improvement on my health and state of mind.

I am determined to return to doing that again full-time, all the time.

Thanks for reading this article. If you enjoyed the photographs here, please visit my official website @ www.tia-international-photography.com for an indelible, visual experience.