

There’s something in psychology called the ‘outcome bias.’
It’s the tendency to say whether a decision was good or bad based on what happened afterward, rather than on whether the decision was good at the time it was made.
For example, if the weather forecast is clear and the sky is blue, I’d decide not to bring an umbrella with me on my afternoon walk. If it started pouring rain later, I might say later that it was a “bad decision” not to bring the umbrella, even though it was a perfectly reasonable choice at the time.
When you look back on your own life, it’s easy to let the outcome bias color your view and let you get down on yourself. This was a bad choice, that was a bad choice, ugh, look how that turned out, why was I so dumb. New business owners tend to do a lot of things “wrong,” but it’s important to remember that usually, we did the best we could with what we had at the time.
Still, now that I’m sitting comfortably a few years down the road, there are three headaches I definitely could have spared myself. I share them partially to have a good Emily-Saliers-eque laugh, and partially in the hopes that someone else can avoid the same troubles.
I should note that these were my mistakes – someone else might do the same thing, and it might actually be right for them. Just like that cute chartreuse Anthropologie sweater would have been a cringeworthy purchase for me, but might have flattered someone else.
Some things just didn’t go so well for me, and here’s why:


Mistake #1: Investing in what I SAW, or the visual trappings of a business, rather than an actual business.
Like some of you, when I started I didn’t know what having a photography business actually looked like. So I spent a lot of time looking at how other people did it.
What I saw was what anyone would see when looking at a blog – well-used Photoshop actions, lovely props incorporated into shoots, sweet blog designs, and what seemed like a host of happy clients.
So I spent a good deal of time in my first year chasing those things – looking at Lightroom presets, browsing props, and fretting over my self-designed blog background.
The problem is, the stuff you see when you look at someone’s blog usually isn’t nearly as important to their actual business as the stuff you can’t see.
Stuff like a clear business plan. A solid understanding of their target client and what that client is REALLY looking for. Skilful behind-the-scenes relationship building with other business owners who also serve their target market. Impeccable customer service, expectation management, and masterful handling of any client complaints. A thorough understanding of copywriting, brand messaging, and how people actually make decisions.
All stuff that, when understood, would have built my business a lot faster than that (admittedly awesome) funky chair I bought as a prop, used once, then discarded.
Not that there’s anything wrong with buying a chair -
but I was so new that I had no idea what kind of portraits I was going to settle into. My style shifted rapidly as I racked up shoots – both personal and paid – and all the props I bought were eventually discarded. I bought them because they were the most concrete thing I saw when I looked at others. (Because Photographers. Use. Props. Right?!?)
But if I’m honest, I could have made do on props borrowed from friends and clients themselves. There are literally worlds of untapped resources right around us if we look and ask.
Instead, I clutched my new props like security blankets, as if they were some sort of proof to myself that I was doing this “for real.”
I wish now I had just held off and sunk all my money into studying client service and the science of marketing and decision-making, and waited to buy “stuff” until I knew more about what sort of work I actually wanted to do. Because studying business, psychology, and client service has done more for me than any visually-apparent thing I invested in early on. And I’m not the only one.
But hey, I know I fall victim to the outcome bias here. How was I to know that chair wouldn’t help me like I thought it would? I suppose they served their purpose – they made me feel better if nothing else.
Oh well. I know now.

Mistake #2: Not paying myself.


After an initial investment in gear, I chose to finance my business growth via bootstrapping. (As mentioned in this post on money, bootstrapping just means that a certain portion of your profits from each sale goes straight back into funding the business. It’s a slow-ish but lower-risk way to fund an expanding new business.)
But, as I am wont to do, I over-bootstrapped a little. For a long time, I re-invested 100% of my after-tax income back into the business. Every cent I made went toward software, gear, and education. (I had other work at the time, so I had the luxury of using the money to finance the business.)
For the most part, this is a good decision. But – and there’s always a but -
Constantly re-investing money, instead of making even a token payment to myself, facilitated some serious frustration and burnout early on. I worked and worked, and though awesome things happened, I didn’t let myself enjoy it.
I felt like I existed to serve my business, instead of the other way around.
Yes, I got excited about some purchases, but some necessities are just hard to get excited about. Shelling out for a monitor calibrator is a little like buying yourself socks for Christmas – yeah, they’re necessary, and you don’t complain, but….well….monitor calibrators aren’t quite as exciting as other things you might buy. ![]()
Much further down the road, I finally “indulged” and took the after-tax profits from a sale and paid for an entire 2-week vacation. I felt guilty about this at first (gah, the courses I could have taken! The lenses I could have bought!), but I was shocked at how powerful and fulfilled this step made me feel. When I saw the impact this could have on my life, it gave me an unprecedented boost and motivation to do more, work harder, and build a business that bore more fruit.
In short, I remembered what being in business was really about. Not just building a business. Building a life.
If I could go back, I would have made token payments to myself from the beginning. Just tiny ones – I wouldn’t have wanted to hobble my growing business. Truly, I needed every penny.
We’re talking $5 so I could go to Starbucks and get a tall vanilla steamer and recharge by reading a book. Or an entrance fee to an art museum where I could wander and fill my soul in beautiful surroundings.
Small things that would have combated burnout by reminding me why I was doing this – to have a better life. To let my business support me. To allow myself to be fulfilled and enjoy what my business was creating.
It would have done wonders.
Mistake #3: Reading all photography blogs instead of seeking a balance between photography and business mentors.
(I strongly suspect this contributed to Mistake #1.)
We should study other photographers, absolutely. Just not exclusively.


In terms of business, there are limits to what you can learn from other photographers. First, you never know from a surface view how someone actually arrived at their pricing, how they got their clients, or how they landed that sweet partnership with a local business. Maybe it was guesswork, a stroke of luck, or some other non-replicable circumstance that won’t really help you. (Or maybe not. You usually can’t know – and truthfully, they may not know, either.)
It’s more productive to look at patterns across people, or principles that can account for more than one person’s success.
This particular post is actually quite an exception on this blog. I actively avoid talking about my own business the majority of the time: It’s just one data point, a pile of first-person anecdotes, a singular confluence of events that may or may not extend to anyone else. It can help, sure (and occasionally make for entertaining reading – like the time that toddler hit my camera with a stick). But there are limits to how much it will help you.
Sure, I’ve used my business as a testing ground for much of what I blog about, but the topics I blog on are backed up by more than just my own experience. I sift through piles of research journals, re-read things I studied in undergraduate and graduate school, pour over countless volumes on business, marketing, decision-making, people’s biases and eccentricities, make regular use of local and online libraries, and search for themes that come up over and over.
Because one person’s experience is only helpful to you so far as it can represent a principle that applies to many people.
And it’s often easiest to see these principles when they come from someone who isn’t in your industry.
If I were a Big Fancy Corporation, I might hire a consulting firm to help me streamline, say, my golf club manufacturing process. The consulting firm I hire will probably not be in the golf club manufacturing business themselves – and that’s exactly the point.
Their value to me is that they see principles that extend beyond my own business. The consultant folks aren’t experts in golf clubs, they’re experts in streamlining, which is what I need help on. I don’t need someone to just tell me about golf clubs – if I’m in the biz, I already know something about golf clubs. I need someone with applicable expertise in locating problems, in implementing solutions, in handling people, in finding and eliminating barriers to success.
I would be shortsighted to only look within my industry, because some of the best solutions come from people who can look objectively and not get bogged down by industry minutiae.
Some of my very best mentors have been musicians, government administrators, public health workers, craft shop owners, writers, wall streeters, venture capitalists, real estate agents, and gurus of business large and small. I learn from them not because they personally run photography businesses – they don’t.
I learn from them because they understand principles that help no matter what I’m doing, they provide untapped paradigms for approaching business problems, and they have a birds-eye view that keeps me from getting mired in industry inside baseball.
Want an uncomplicated, business-boosting tip? Stop reading all your current blogs for five days, and use that time instead to search out new ones outside your industry. Or, if you prefer, delete one uninspiring blog (preferably that person you keep comparing yourself to, and feeling bummed as a result), and replace it with a fantastic blog far outside photography.
I wish I had done this from day one.
As we conclude this tour through the Ghosts of Jenika’s Business Past, let’s remember one thing:
We’re going to bungle some business stuff. Some people, like me, might bungle more than others. I do suggest that you invest in education, pay yourself, and read widely outside the photography industry – you’ll avoid things that took me (and others) months to sort out.
But when mistakes come – and they will - keep a two-hundred-dollar attitude when working with clients, forgive yourself, and don’t let it bring you down. Most successful entrepreneurs tried several things and had many false starts before they landed on “the one” – accept that this is a process, educate yourself as much as you can, and make the best decisions possible.
Then share your mistakes with others. Who knows – it might help someone else![]()
~
P.S. Total tangent alert: One mistake you definitely don’t want to make is messing up your taxes.
USA folks: I was so excited to see this new little e-book from Alicia Caine called Keep Calm and Get Your Taxes On. I’m a proud affiliate of Alicia’s, and I was so stoked when I saw that she’d gone to the trouble to answer common burning tax questions.
She worked with an accountant to create this, and it covers everything from mistakes to avoid, how to make sure you have enough to pay your taxes, when you’re considered a hobby vs. a business, when you have to pay quarterly or self-employment taxes, and how to choose a tax professional. In my opinion, it’s a steal at $29.
Keep Calm and Get Your Taxes On is only available through 10/24. If you’re in a tax funk, check it out and see how it can help!







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