For being my 5th year “in business,” 2017 honestly felt more like it was my first year in business… or at least the first year where I had any real clue what to do… and where imposter syndrome didn’t kick in whenever I claimed to be “in business” or be “an entrepreneur.”

Year 1: Freelance

My first foray into business back in 2011/2012 was more in the way of “freelancing,” without a thought into target markets, proper pricing models, financial projections, bookkeeping and contracts. It was very much a luck-based and “take what you can get” mindset without any intention.
As luck would have it, though, I landed my first client by randomly by walking down the street in Nyack and simply making conversation with someone carrying 2 professional cameras. She was an editor at Newsday Westchester… and this chance encounter turned into a year’s worth of steady work, which allowed me the luxury of not really considering alternate revenue streams, ie finding other clients. (I did have other gigs on occasion, which typically came about randomly, and one other regular client in web design, but it really wasn’t intentional.)
But… then, on one hot summer day in 2013, almost exactly one year after the fateful walk down Main St in Nyack, I received a startling call from my editor.
“As of a few minutes ago, Newsday has decided to close its Westchester office. Don’t worry about the photos from this assignment, or the rest of the day. Charge us the whole day rate for today and submit your final invoices.”
And, thus launched the true start of my adventures “in business”… whatever that means. I thought.

Year 2: Blank Slate = lots of learning, no money, and lots of debt

That day, I learned the true value that having multiple simultaneous clients would offer… because I didn’t really have any others, and therefore nothing to fall back on.
I took this as a sign to really “figure out” what it meant to be “in business”…
Which, at the time, apparently meant not really making any money because I had a LOT of learning to do, and not the first clue of how to actually get a client, let alone what I would charge if someone wanted to hire me.
During this phase, from mid 2013 to late 2014, I spend a lot of time learning, reading, attending events, networking, spending money I didn’t actually have (to invest in myself and my network), and likely, making a fool of myself.
I started joining “free” networking groups on, going to the local Chamber of Commerce’s mixers and educational seminars, joining professional associations in photography, going to photography business seminars and conferences, and…. listening to a whole lot of School of Greatness podcasts.
I even hired coaches and consultants that were way out of my price range…
I was stubborn about not getting even a part time job (though I did try, now and then, with no luck) always feeling like I was on the brink of my next, “big break.”
To be fair to my younger, more naive self, I made the best decisions I could have made at the time (and hey, it’s led me to where I am now).
By fall of 2014, I couldn’t take the financial hardship and debt accrual any more…

Year 3 & 4: Getting a job…. does not mean you are a failure (unless you let it).

I couldn’t take the pain of borrowing money just to pay my minimum payments or wondering whether I would have enough money on X day of the month when the next auto payment would be withdrawn. It felt like I had bills due every other day (it wasn’t really, but it felt like it)…
So, I got a part time job at Barnes & Noble…
Boy, did that feel like a major failure. I felt like I was a failure…I rationalized by saying it was just “for the holidays.”.. and then felt even more like a failure, when I extended my tenure past the holidays… ultimately staying for 2.5 years.
It took a long time for me to realize that getting a job as a means to steady income while in pursuit of your ultimate goal of running a business, is not a failure… it’s the smart thing to do… and that experiencing a failure (or set back or undesired result) does not mean that I am a failure… it is an opportunity to learn and improve, and it’s only a true “failure” if you actually give up.
I also realized, that, as jobs go, my situation was pretty good.
When I started at B&N, they knew I had my own thing going… and they were super flexible with me in terms of scheduling. Not to mention, the perk of borrowing hard cover books allowed me access to a wealth of knowledge in the business section. AND… when they became serious about pushing us into a more sales and customer service oriented role (from task/transaction oriented), I took it as an opportunity to practice what I knew would be an important skillset in my own business… selling. And…of course, in people reading, psychology, how to manage a conversation, how to ask for the sale, and learning what buttons to push/when to push them. Not to mention, the psychology of sales/selling and developing my own sense of a philosophy around sales. (Read more about this experience and what I learned in this blog post.)
Because I let myself engage at the job and find the real benefits I could gain from it – outside of a steady paycheck – I was able to excel… and even earned the employee of the month status twice for my sales efforts.
Even though I was able to make the position my own, and I learned some important skills and some important lessons about myself, the pain was real. I was always battling an energy problem… mental, emotional and physical exhaustion.
There were days I got home from work, and simply passed out asleep. There were days I got home at 11 and had to open the next day, but needed to stay up and do client work or work on the business. There were times I had off for a few days and I literally dreaded going in for my next shift.
I longed to quit for months, if not over a year. But, I was afraid. My business was not ready. I was not ready.

Year 4: Living a double life….

During this whole period at B&N, I was still working on my business… and myself. I did everything I could to help my mindset: listen to podcasts (favorites included School of Greatness & Marie Forleo), read a lot of self-improvement and business books (including: To Sell is Human, The E-Myth, and How to Win Friends and Influence People), journal, talk to certain friends… I worked on my network. I started building strategic alliances. I even started my podcast.
And, in the fall of 2016, I had another one of those “serendipitous moments” like in Nyack… but this time, it wasn’t the same. I made an offer, on a whim, for a strategic alliance that involved office space and business coaching … which has really helped propel things.
This alliance provided me both the physical space I needed to do business outside of the home, which gave me more of a feeling of my business being real and something outside of me. It also offered the mental/emotional support system I needed to stay accountable and motivated, even if I wasn’t necessarily seeing the exact desired results, on time.
After that, something changed in my mindset. Something clicked. I started to see different “problems” (eg how to create consistent and predictable revenue streams, how to create repeat photography clients, etc.) and come up with creative ideas to solve them. Ideas kept coming, and, as I said above, I now had a support system that would keep me accountable.

Year 5: Breaking Point… and Turning Point.

That leads me this year.
I started this year with two passions: 1. leave my job and 2. make my business work so I can move.
And then… something happened in my personal life that completely shifted my whole being.
My boyfriend (of 3+ years at the time) asked me to move in with him.
We had been growing closer, but I was in denial. I had a major desire to leave this geographical area, and because of that I couldn’t fully commit in our relationship. (He had his own reservations in committing too…) And our relationship had always been “temporary” with the understanding that I would be leaving… and so it would end.
So, you can imagine my shock.
It took me a few months to go for it… but in the mean time, I started to question everything.
I was still following through on my business plans and working at the store… and landing my first real major projects (in the multiple 4 digits per project). I even had some cool successes, like doing projects for magazines that were sold in Barnes & Noble.
But finally, I just couldn’t continue.
I was exhausted all the time from working 2 jobs (B&N/Business) and living in two houses that are 45 mins away from each other. I felt so scattered and I never knew where I would be sleeping. I pretty much had to have bags packed at all times. I felt as if I were living out of my car.
Not to mention, the continual discrepancy between how much I could earn in a day with my clients, versus the time it would take to earn the same amount at my job (let’s just say, it could take a month or two).
Scheduling became a major problem as clients and prospective clients were becoming more prominent and the system of scheduling at work became more rigid.
I decided I would take some vacation time to clear my head and re-evaluate.
As it turned out, I used that time to move in with my boyfriend.
This, and receiving checks from those projects I mentioned before, gave me more confidence to finally cut the cords and take the leap.
In May, I finally left B&N to pursue business full time.

Fear… and passion.

Leaving my job was terrifying.
I couldn’t help but wonder what was going to happen and fear that I would wind up back where I started… penniless and in major debt.
I did a lot of reflection to convince myself of why it wouldn’t be like the first time (when Newsday closed and I was left stranded).
I realized… “Hm… this is not the same. This is a choice, not something that is happening to me without my say. I now have more skills and knowledge of business, as well as a plan. I have enough money to last a few months… so if I don’t get another client for a few months, I will be fine. But, I can probably get another client before then. And… if I don’t, well I can always get another part time job if I have to.”
At the same time, being more invested in my relationship made me re-evaluate my motives in moving and examine what it would mean going forward, particularly for my business.
I realized that the stakes are higher now than ever… because I have to find a way to make it work… here.… and asap.
This realization gave me a new sense of passion for finding zen in the market, or finding what will work. It has inspired a new sense of curiosity and desire to really understand the market in the Hudson Valley. It’s inspired me to do things that I might have otherwise avoided due to the fear of rejection or of hearing something I don’t want to hear.
I’ve learned the value of testing my ideas and assumptions… in spite of possible discomfort if I am inaccurate… the value is the opportunity to learn and course correct before I go too far down the wrong path, wasting a lot of resources.
And, I’ve gained even more confidence in other details of my business, such as pricing, and finally have begun to define proper systems and evaluate how I do things, so that I can improve the processes with intention.
I’m still learning, and I still have a lot more to figure out… but I know that I am on the right track and I have learned, probably the most important lesson of all: I don’t have to fear running out of money… because I know I have the skills to generate revenue.

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