I’ve Been in Business 11 Years: Here’s What I Wish I Did Differently (And What I’d Keep the Same.)
My junior year of high school, when other students were narrowing down their dream jobs, I was fantasizing about entrepreneurship.
At 16 years-old I knew I wanted to be a small business owner. Every decision I made from my course schedule to where I’d attend college and what I’d study was influenced by my desire to become self-employed asap.
Even the car I drove was a factor. (A green 1999 Volkswagen Beetle, which later inspired my brand — and saved me a bunch of money on gas!)
At 18 years-old and in the midst of college, my dad encouraged me to make my little photography business legit, and I became the owner of an official LLC on October 9, 2013.
A few years later, at 21 years-old, I quit my full-time job and realized my dream of self-employment.
Eleven years later I still work for myself, but I traded photography for marketing and small business mentoring. (I still have that ’99 bug, though!)
If I had a do-over there are certainly things I’d change. And there are other things I totally nailed from the beginning that I’d do the same. Here are my regrets and wins from my early days of entrepreneurship:
What I’d do differently:
Charge more.
Undercharging stunted the growth of my business and led to major financial stress years into self-employment. (I’m still paying myself just this much.)
I thought that because my services were easy to me and because I enjoyed doing them that they weren’t worth a higher rate.
But I didn’t take into consideration how long it took me to learn how to do what I do. Something being easy means you put in the time and effort to make it that way. And shouldn’t we enjoy what we do?
I also underestimated the cost of doing business, such as software, insurance, and all that photography equipment I needed to invest in.
And while I knew self-employment taxes were going to be high, it was still a shock when I discovered how high they actually are.
I’m confident in my current pricing but didn’t get to this point until recently. If pricing feels like throwing darts to you, I share a few strategies in my online course, Begin Your Business.
Invest in a more detailed contract and set stronger boundaries with clients.
While you may not end up in court, having a contract to fall back on allows you to enforce your policies with clients.
It’s sad how often people don’t hold up their end of an agreement, take way too long to pay you, or don’t credit your work when they’re supposed to.
Contracts lay out your payment terms, state what’s included in your offer, set project deadlines, enforce your copyright, explain what goes down if the contract isn’t followed, and they protect your business.
While I’ve had a contract for every photo shoot, website design project, and marketing client I took on from the start of my business, it was lacking.
I had purchased a two-page photography contract for photo shoots, and for marketing projects, I modified the contract used by the marketing company I previously worked for.
This contract, even for website design, was just three pages long. It left out policies that led to projects dragging on for months with too many rounds of revisions.
In 2023 I discovered The Legal Paige and purchased her website design contract template which expanded my contract to eight pages.
My new contract includes a project timeline with fees if it’s not followed, a set number of revisions, accepted forms of communication, and additional clauses I never would have considered.
If your business is a brick-and-mortar, you’re a maker, or another type of business owner, it’s still essential to have policies and terms in place.
Be more discerning with the work I took on.
I’m a recovering hustler. If I had the opportunity to make money, I would.
Which led me to designing a photo album for one client and a photo slideshow for another. This would make sense if it were part of my photography business, but I hadn’t photographed either client. I was using photos they provided.
Both projects required me to learn software I haven’t used since, took more time than I had planned for (due to my lacking contract), and left me grossly underpaid.
Now I only take on work that’s in my zone of genius, which is the work you’re good at and enjoy.
If my business needs a revenue boost, I’ll offer work I’m good at but don’t necessarily enjoy, but I’ll never again offer a service outside of my zone of genius.
I also have a screening process for clients. If I have a sense that I’m unable to provide what a client is looking for or that they’d be difficult to work with, it’s a pass.
Been wiser with advertising.
The majority of my photography clients came by referral or search engine optimization (SEO), both of which are free.
But I still went down the route of feeling like I had to pay to play and spent hundreds of dollars on Facebook and Google ads, neither of which drew business.
I may have received more likes on my boosted Facebook posts, but passive liking never lead to sales, just an ego boost.
I also became caught in the trap of vanity marketing, falling for a sales pitch from a “who’s who” organization that cost me over a thousand dollars.
And when the publisher of Martha Stewart Weddings reached out, I paid for the $1,500 ad in an affiliate publication in the hopes it would later lead to a feature in the coveted renowned publication. It didn’t and the ad generated zero leads.
Stayed in my job longer.
I quit my job before my business was able to support me. We tend to overestimate our income projections in the early years and underestimate expenses and taxes.
Keeping your job while growing your business allows you to build an emergency fund both for yourself and for your business, be discerning with the work and clients you take on, and build recurring revenue so when you do quit your job, your business can immediately support you.
Here’s what I recommend having in place before quitting your job (and what I wish I did).
What I’d keep the same:
Get legit.
When my dad saw that I was taking my business seriously, he encouraged me to register it as a limited liability company (LLC).
I also applied for an EIN (employer identification number) to protect my social security number, purchased a business insurance policy, and separated my personal and business finances by opening a checking account for my business.
And later, when I left my office space, I rented a post office box to protect my personal address.
Fortunately I’ve never faced a lawsuit, but I did place an insurance claim when I dropped my external hard drive. My business insurance paid for itself that year.
Strive for professionalism.
To set myself apart from the competition I strove for professionalism.
My business was an LLC and insured, I designed a website and registered an email address at my own domain, and ensured my website and marketing materials were always clear and on-brand.
When I received an inquiry I’d respond within hours. Some clients later shared that they hired me due to my responsiveness.
Be consistent.
I was in college and worked a part-time job when I started my business, which later turned into full-time job when I graduated.
Time was limited, but I promised myself I’d complete two tasks for my business every day, even if those tasks were simple like responding to client inquiries or creating a social media post.
The big tasks, such as designing my website or writing a business plan, were broken into smaller tasks.
There is a time investment when starting a business, which can be easy to feel overwhelmed by when you’re still working and have other responsibilities.
But small, consistent effort leads to steady, stable progress. It also builds the habit of working on and in your business.
Whereas sporadic bursts of effort can lead to inconsistent results and burn-out.
Be scrappy.
The money from my bank teller job went to college tuition, gas, and savings towards my future home.
Because I prioritized homeownership over investing in my business, I opted for secondhand photography equipment and continued using my college laptop for business purposes.
And eleven years later, I haven’t upgraded either.
I also learned how to do my own bookkeeping, website design, and marketing, which gave me the skills to open a marketing business later on.
It’s better to start small and reduce costs in the beginning for multiple reasons: You’ll likely be profitable more quickly (which can lead to self-employment faster), if you decide to discontinue your business you won’t lose out on a big investment, and entrepreneurs who build a foundation on wise frugality are more likely to persevere through challenges and set-backs.
Never would I recommend cutting corners, but starting as small as you can builds your business on a stronger foundation.
Pivot.
Soon after I started my photography business, I learned that I really don’t like weddings. Which is where the bulk of a portrait photographer’s revenue comes from.
It felt like I had spent years going down the wrong path, chasing a dream that left me miserable.
Once I moved through the panic and “what have I done?!” feelings, I reflected on what I loved about my photography business: vendor photos and the marketing aspect.
Which inspired me to pivot to offer small business marketing and commercial photography.
Soon my community began asking for marketing classes, which encouraged me to create the online courses I teach today.
Jumping right in.
The aspiring entrepreneurs I talk with are terrified about the economy and if now’s the right time to start their businesses.
I was living rent-free with my parents when I started my business, so the fears of reality weren’t there for me.
Now that I have more responsibilities — and debt — I understand where these people are coming from.
But there’s never a “right” time to start a business, and you’ll never have enough knowledge either. I didn’t know what “LLC” meant until the day I applied for one!
It’s okay to figure things out as you go, as long as you’re responsible about researching what you need to know.
You also don’t have to uproot your life to accommodate your business either. Move with consistently, start small, but get going.
Owning a small business is not the easy path. It will lead to challenges you’d never face as an employee, require you to gain knowledge in multiple areas, and sets you up for way more responsibility.
But if approached with respect and determination, owning a small business can be the most rewarding path.
You’ll gain lessons, experience, and so much pride. And when your business takes off, you’ll have a heck of a lot of freedom too.
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Just getting started in business and looking for a roadmap? Check out my Begin Your Business online course. We’ll cover everything from pricing to forming an LLC, assembling your team to getting your first clients, and everything in between.
Been around the business block and looking to grow? My Self-Employed School online course provides a deep dive on topics including website SEO and design, e-newsletters, social media, public relations, and more. It all culminates in creating an easy and effective marketing strategy for your business.
Hey there! I’m Meg:
LOVER OF CATS, ROLLER SKATING, AND VW BUGS
I also love business and share all kinds of tips and resources to help you grow yours.
Ready to get business savvy? Subscribe to my email newsletter. ;)
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