10 Things That'll Make All Entrepreneurs Say "Same" ~ Wisconsin Photographer

Let's face it, being an "entrepreneur" or in any way self-employed can be a daunting task. It's all on you and running the show, so to speak, isn't for everyone. But, for some special unicorn people...it's all they CAN do. Entrepreneurship is WIRED into their very being. It's like AIR. You NEED it. You can lament the pitfalls all you want, this is all you will ever be. 

That doesn't mean it doesn't come with a few bumps in the road or laughable moments....however..... 

Sit down, grab a cup of joe, and let us all enjoy the tale of an entrepreneur. 

1. People Don't Think You Have a Real Job

I've owned my own business since 2008. For awhile there, I owned two businesses: one service-based and one retail location that sold a physical item. I still had a hard time explaining to some friends and family that when I was "at work" I was actually "at work". When Saturday rolled around, I actually have "to work". When I'm home in front of the computer, I'm working. 

I think people believe, sometimes, that if you don't have a boss, a set schedule, or a building someone else owns and runs to go to every day at 8AM, you don't really have a "real job". That you can easily say "ahhh, forget it....I don't feel like working today" and spend all day with your feet up watching Forensic Files (not that I've EVER done that, I swear). 

See....Really working. I swear ! 

See....Really working. I swear ! 

2. Where Did All My Money Go?

Unless you're some sort of high roller who has no "off season"....in most cases, small businesses have their "busy time" and their "DEAD ZONE". Retail businesses often see an uptick around Christmas. We owned a record store, so April was big for us too (Record Store Day and all)

For photographers, May through October you are "makin' it rain" and then some years I feel like I'm one second away from scraping the bottom of my couch for loose change. You always say you're gonna "plan ahead" for the lean times....but life happens too and not everyone is mega-organized. I try to be mega-organized. 

So, if you wanna reach favorite client status? Plan all your stuff in the off season and hire us then :) 

3. Your Personal Life Can Be a Bit of a Mess Sometimes

Let's be honest....if we choose to be entrepreneurs we live, breath, eat, sleep, and dream our jobs. They are our babies....we cultivate them and work long long LOOONNNG hours to make them an everyday reality.

There are some folks out there who are REALLY good at "balance". Having three children and a husband I honestly think balance is a pipedream in and of itself. I don't so much balance as wobble....teetering on the edge of insanity...most days during busy season. 

But I'm a bit weird. That's kind of how I like it. 

I have gotten a LOT better at managing work and home though since the early days of Type A. My husband MIGHT disagree, but I spend a lot less time editing than I used to (thank you kick-ass workflow) . When we owned the record store we realized, quite quickly, that having young children, running two businesses + a full time job on top of that for the hubby just wasn't a great idea. Vinyl was my husband's passion (still is)....but the store wasn't really the best way of feeding that dream. 

4. An Upset Client Can Ruin Our Day, Week, Month....hell, YEAR. 

You're in business....you're not going to please everyone. Some people are really, really hard to please. Sometimes you goof up....because you're human. Sometimes....(yup..sometimes) people be crazy. 

When I used to work in retail in high school we would get complaining customers sometimes and I never gave it another thought past their asking to speak to my manager about their being overcharged on Charmin Ultra or the fact that maybe I didn't smile at them wide enough (that never happened....but, like I said, people be crazy). 

It wasn't my fight to fight. It was the managers. It was Walgreens. I'm not Mr. Walgreen. I made $7.35 an hour.....I wasn't paid enough to care. 

Sounds harsh, but it's the truth.

But when you are the sole person acting as the face of your business and someone is unhappy with you? God, I don't know about you....it WRECKS me. I ruminate over how I can fix it....I obsess over what I did wrong.....until the client is satisfied I am not satisfied. 

5. Tax Time Sucks. A Lot. 

I used to be one of those people who kind of looked forward to getting my tax refund. I didn't CARE that it was just because I had overpaid all year....I was goin' SHOPPIN'. 

Since being self-employed, refunds...well...that's something I get to hear about other people enjoying. They've been replaced by complicated tax code, quarterly estimates, sales tax coming due, and cursing the day April 15th was born. 

Find a good accountant. Trust me.

Work never stops (I swear, that is probably work related....LOL) 

Work never stops (I swear, that is probably work related....LOL) 


I've never been a fashionable person. I once wore khaki's and cherry printed socks to my office job with clogs. 


But since becoming self-employed, I really don't have to worry about "dressing up" unless I'm meeting with a client (hello black dress pants and a nice black shirt) or going to a wedding (same.) 

Otherwise, it's all stretchy pants and hubby's t-shirts up in this house. Hair knotted on the top of my head. No makeup. 

And it's all good. The only person who sees me is Bridget and she doesn't care. She's gonna just puke on me anyway.

7. Comparison. That Dirty Thief of Joy.

If we sit there and say "Oh, I don't compare myself to other people in my field. They're doing their thing.....I'm doing mine". Well, okay....I'd like to know what you're on and can I have some? Because that's just not.....normal. We compare ourselves to the success and failures of others around us. That's what we do. That's what BUSINESSES do. They keep a tab on the competition because of best practices....because you are a player in the industry....and because we are all a bunch of competitive, nosy human beings. 

But, if we delve too far down into that internet rabbit hole and start becoming pre-occupied with what everyone else is doing better, worse, more than or less than us......our own work will start to suffer. 

So, try hard to keep your eyes on your own paper. I know, it's freakin' hard. 

In Photography it's REALLY hard because most of us live our business lives out on the internet. We have to tell each other WHAT we are doing and WHEN and HOW all the time. It makes us look successful and busy. Could you imagine if other occupations did the same thing (Dentist: I just got back from a RAD root canal!!! Wait until you see this, folks! It was AMAZING!!!) 

Photography also has a low barrier to entry and no checks and balances. Basically, ANYONE with enough gumption, access to Facebook, and a camera (hell, even an iPhone7, apparently. RAW!) can hang out their shingle and declare themselves a "professional photographer". There is no licensure...there are no tests to see if you know what you're doing. Even the IRS is so back logged they're obviously not keeping very good tabs on who isn't paying their taxes (we know who you are, seriously). So, it can be REALLY REALLY hard to just ignore all of that and say "I'm good over here in my own corner. Really"

Some days you're just looking at Facebook and saying "Oh CMON!!!!" 

Admit it :) 

8. STRESS Becomes Your New Roommate

Deadlines. Self-Imposed expectations. Client complaints and requests. Money worries. Taxes. Travel. Expenses and Debt. Personal life issues. 

There is a monumental amount of stress involved in owning your own business. Especially if you tend to be a bit of a worrier (throwing up my hands here in solidarity, my anxious brothers and sistas). Basically, you have eleventy-million plates in the air at one time and you have to put out an aire of cool, calm and collected so people will trust you and hire you. 

I thrive under pressure, always have. It's that whole Type A/Control Freak side of me. If I'm NOT stressed I start thinking I'm missing something. 



9. You Contemplate Quitting

I always hesitate to call myself an "artist"....artists to me are people who OOZE creativity. People who don't really have to work at creating phenomenal things. I have to work at it. Some days I just sit, staring at my computer, willing my brain to think of something great.

Some days it doesn't come.

I'm a business owner. With everything that comes with that. And sometimes it just gets HARD. So hard that you seriously contemplate finding a 9-5 to regain some semblance of normalcy. 

I did this last year. I took on a 9-5. Non-photography related. I cut back on all of my photography work and I focused solely on this new job. I had great thoughts of the regulated schedule and the income that would come at the SAME TIME every other week. I hadn't had that in SO LONG that I thought it was what I wanted.

But, some of us are simply wired differently. I was raised by an entrepreneur. I have NEVER been very good at having a boss. When I was younger, people simply passed it off as a problem with authority (maybe.....) but really, I just have this insane drive to do things my own way. To make my own decisions. To buck the status quo sometimes. If I'm not steering the ship, I'm not happy. 

So, that makes ALL of it worth it. I came back to self-employment because I know that this is what works for me and my family. 

But I think we are kidding ourselves if we say we haven't thought of quitting the whole shebang at one time or another. That's how hard it can get.

10. We Are SO Lucky

Even on my WORST days (and there have been some doozies.....) I know how fortunate I am. There are many many out there who dream of having their own business that supports them and their families....and I do. There are many who dream of having a job that allows them to not only make a good amount of money but to stay home with their children and have the freedom to (for the most part) craft their own schedule. I do. 

We are very very VERY lucky people, us entrepreneurs. For all the hard parts.....I still remind myself of this every day. 

So hang in there, fellow business owners! We are the few and the proud! Know that whatever you're experiencing right now, we are all sitting here at our desks saying "Yup. Same." 

Amanda Reseburg