Small Business Owner Regrets: What I Wish I Had Done Differently
Raise your hand if you’ve ever had a great small business idea but then immediately felt overwhelmed on how to bring it to life or take action on it…(I’m raising mine!)
Where do I even begin? How do I get people to care about what I’m selling? Can I be successful without 10k followers on Instagram? How does online marketing for your small business even work? What should my social media strategy be? How do I attract clients? Do I need business coaching for my small business?
As a new or aspiring business owner, these might be just a few questions you’ve got running through your mind at any given moment on top of an endless to do list.
When we’re first starting out, it's natural to make mistakes and do things that years later we’ll be kicking ourselves for! But it’s all part of the learning process, and for small business owners, our journeys are never quite linear.
So, in this blog post, I’m opening up about some of my personal experiences and regrets, highlighting the things I wish I did and didn't do when I first started my own business. By the end of this post, you’ll have an idea of what action to take on in your business and what things to avoid!
First things first, let’s clear up a few things, okay? If you follow along with a lot of small business content on the ‘gram, there’s no doubt that Instagram is flooding your feed and explore page with sponsored ads from girl bosses and boss babes promising to teach you how to make 10k a month from your phone on the couch. There’s LOTS of content creators using empty promises to market their courses, and while I’m not trying to throw any shade, because hey, I’m a course creator as well, I do want to caution you that there’s a LOT of marketing bologna that we’re seeing online right now that can lead us down a confusing path filled with fluff and no clear direction mixed with a whole lot of unrealistic expectations for what our business should or shouldn’t look like.
So let me cut the crap for a moment for us and get into some real truth about common myths and misconceptions of owning a small business, because you deserve to hear the truth from somebody that not too long ago was sitting in a college dorm room with a dream and a goal to simply just make money doing something that I enjoyed, that would one day become something bigger than I could ever imagine…
(PS - interested in learning more about my story? Check out this video from when I finally made the decision to quit my full time job in November of 2022 to pursue my own business full time)
Common Myths + Misconceptions about Owning a Small Business:
Instant Success
Many people believe that starting a small business will lead to instant success and financial freedom. Register your business and BOOM additional income stream secured! Nope. Let me be totally real with you for a moment. I had been in business for two years already and I decided to do a big launch of products for Christmas. I thought I had marketed it so well, I was so proud of my collection, and I got ONE SINGLE SALE.
I’ve already been in business for over two years? How am I still having failed launches like this?
The reality is that every small business owner goes through failure, at every stage of business. Every year. I don’t say this to discourage you, but to rather encourage you that your “shortcomings” are learning moments that don’t mean you’ve really failed, it just means you’re learning. The most important thing, the defining moment for any small business owner or entrepreneur, is what you choose to do AFTER you’ve failed.
Remember, building a successful business takes time, effort, and perseverance.
Work-Life Balance
There is a misconception that owning a small business will naturally provide more flexibility and work-life balance. However, in the early stages, entrepreneurs often find themselves working long hours and wearing multiple hats to keep the business running.
Part of what led me to quitting my job to go full time with my business was the fact that I was working so many hours that both my mental and physical health were suffering immensely, and I knew time was running out for me to continue on that path. I was getting migraines every week, often so stressed I was brought to tears before bed most nights. It wasn’t a good way to live!
Looking back, I wish that I would have made the decision sooner so that I could have spared myself the exhaustion and physical complications, but I know everything happened in God’s timing just how it was supposed to.
Owning a small business alongside my full time job absolutely gave me more financial freedom, but it didn’t necessarily give me freedom with my time. That part didn’t really come until later. But that’s okay!
Easy Money
Running a small business is not a shortcut to easy money. It requires careful financial management and strategic planning.
Anyone that promises you easy money you can make from your couch or phone is likely not giving you the full story.
If somebody sells a course to you on the idea that you can make six figures from working only a few hours a week, run in the other direction.
While this might be possible for some, it’s not a realistic picture of small business and entrepreneurship for those that are first starting out. There’s no way to avoid putting in hard work when it comes to owning a small business. There aren’t quick fixes.
The only true shortcut I believe in for small business is investing in coaching and education so you can learn things the easier way rather than making lots of mistakes and wasting your time when you could have gotten the handbook from somebody else! This handbook is exactly what I strive to provide my students in my classes for small business owners.
In my opinion, investing in education for your small business, whether it’s from me or another trustworthy source, is the closest you can get to a shortcut in business, but even then, it doesn’t mean you’re not still going to be working hard!
Stress-Free Work
While owning a small business offers independence and the opportunity to be your own boss, it also comes with the responsibility of making critical decisions and shouldering the risks—and in my opinion, that can be stressful!
Owning your own business and being your own boss is one of the GREATEST blessings in the world, but that doesn’t mean it’s not still hard. One of the things I’ve found to be the most stressful since going full time with my business is that when there’s a problem, nobody else can put the fire out but me.
When I had a boss, I could go home at the end of the day and essentially forget about work until the next day. I didn’t have to deal with the consequences of an unhappy client directly, and if we lost a client, it wasn’t affecting my personal paycheck.
Now as the CEO of my own gig, all of it affects me directly, and when there’s a problem or conflict, I’m the only one that can deal with it.
BUT, what’s more stressful? Going to a job every day that you hate. Sitting in an office feeling like the life is getting sucked right out of you. Crying in the car on your lunch break because you aren’t doing what you truly love. That’s way, way worse and much more stressful.
So I’ll take the stress of being a business owner over the stress of working a job I hate for a boss that refuses to give me a raise any day ;)
Limited Responsibilities
Small business owners have to handle various tasks, from operations and marketing to finance and customer service. Of course I wanted to own my own business because I wanted to make money doing something creative, but graphic design isn’t the only thing I’m doing. In between the fun stuff, I’m doing the sales, the customer service, the bookkeeping, the everything else. So don’t think that owning your own shop means you get to skip out on the boring stuff.
Now that we’ve got that out of the way, let’s dive into what you’re actually here for, things that I did/didn’t do in my small business that I regret - in other words, I made the mistakes so you don’t have to!
Not getting a professional payment processing system in place.
I took payment on Venmo for an embarrassing amount of years. “DM to order” was my call to action. YUCK!
It’s just not the most professional look for a small business owner that’s looking to establish a professional brand.
Look, I’m all about running a lean business, but if you’re serious about entrepreneurship, it’s not a matter of if you’ll set up an account with an online payment tool or CRM system, but when. You’re literally going to have to make the switch to something more professional at some point, so why not just bite the bullet and do it now? Your future self will thank you.
Looking for a more professional way to accept payments but not sure where to start? I use Honeybook and you can get a discount for 25% off your first year of Honeybook right now by clicking this link.
Waiting to start an email list.
I’m not kidding y’all I literally still lose sleep over this sometimes. Like, to quote We’re the Millers, “no ragrets” but truly some regrets about this. Which is why when I work with clients as their ongoing monthly marketing support team, email marketing is one of the things we ALWAYS spend intentional time on, and you should too!
DIYing my contracts for too long.
AKA waiting too long to invest in professionally written contracts. I spent YEARS just throwing contracts together and crossing my fingers that people wouldn’t take advantage of me because there’s no way my original contracts would hold up in a court of law. And then when I did have somebody violate the conditions of their contract, I had no way to enforce what I wrote or take legal action. That was about the last straw for me before I decided it was finally time to invest.
If you’re not ready to have an attorney write your contracts for you completely custom, I’d recommend purchasing a contract template written for your industry by a trusted source.
Another plug for Honeybook, they have contract templates available for you to use in their platform! Click here for your discount.
Having no contracts at all for client work (in my early days).
Literally this was dumber than dumb. What was I thinking? But hey, we all start somewhere! This really bit me in the butt when I asked a client to not do something they were doing with my art because I hadn’t given her the permission to use it in the way she was using it, and she CLAPPED BACK AT ME in full force because I never had her sign a contract, and hey, she was kind of right. Do I wish she would have approached me with more grace? Sure. Did I cry about it before bed? Absolutely. But although that interaction was difficult, it showed me that I needed to quit messing around and get serious about my client onboarding process.
Client contracts. for. everything.
Working for exposure.
Y’all I’m not kidding, I really did this. For a LONG flipping time. While the exposure definitely helped me grow an audience, it is true what they say, exposure doesn’t pay the bills.
While I certainly don’t think there’s any shame in working for free temporarily in exchange for testimonials when you’re first starting out, I really think you have to draw the line somewhere.
I waited too long to do this because I was chasing exposure and reach. Watching numbers climb was addicting. And in the height of the ‘Vid in 2020 when there was nothing to do but stay inside, I was checking my Instagram analytics as often as I could just for the rush of satisfaction it gave me to watch these vanity metrics skyrocket.
I had garnered thousands of followers but felt like I had nothing to show for it. I felt like an absolute imposter. While Instagram has been helpful for me and does help my business in finding new leads, it’s not the ONLY way to build a successful business and it can’t be my only focus (or yours).
Eventually, years ago I finally worked up the courage to say “no” and stop working simply for exposure. I wish I had done it sooner. I cringe thinking about the amount of time I spent working on content for other people for free all in the name of exposure.
Wasting time trying to be all things to all people on all platforms.
You guys I for real hate TikTok. I don’t trust the app, I don’t even like having it on my phone and I just don’t love the platform in general. I truly do not feel like I need ANOTHER platform in my life to be addicted to scrolling. Instagram takes up more than enough of my time.
I started trying to post videos on TikTok just because I saw so many other creators posting TikToks, it felt like I HAD to be posting on there. Until I re-evaluated and remembered that most of my target audience is on Instagram, YouTube and Pinterest, not TikTok.
And also, if I don’t like the platform, I don’t have to be on it. Could I spend time creating content for TikTok that might perform well? Sure. Is it really going to move the needle forward for my business from a financial perspective? I’m just not confident that the answer to this is yes.
A quick litmus test I give myself for anything I’m investing my time in for growing my business is asking myself this question:
Is this a money making activity?
And if the answer is no, then usually when I’m in busy seasons or catch myself doing too much or trying to be too many things or trying to do too many things well, I know that it might be necessary to either press pause on that particular initiative or set it aside indefinitely. Bye TikTok.
Waiting to register my business. This is literally one of the first steps you should take as a business owner, and I walk my students through this whole process in my live group coaching program for small business owners, the Creative Entrepreneur Accelerator Program. Click here to learn more and jump on the waitlist (next round opens up for enrollment in January of 2024!)
Being wishy washy about my pricing.
One thing I learned from a recent strategy call with my business mentor is that my pricing should be non-negotiable. Like I’m talking as non-negotiable as brushing your teeth before bed or keeping the thermostat at a crisp 67 degrees at night when we go to sleep. No. touching. the. thermostat.
It might feel like you have to be flexible on pricing in order to keep the interest of potential clients or prevent new customers from completely turning you down or writing you off because it’s “too expensive”, but truthfully, lowering your rates or letting someone negotiate you down in your pricing is cheating yourself.
You want the clients that say yes with no hesitations, not the ones trying to get you to come down in price and cut them a deal. And honestly, if a client is trying to do this, it’s typically a red flag.
From experience, it’s typically the highest paying clients, or the clients that raise no disputes about your pricing that treat you with the most respect. The potential clients that immediately dispute your pricing and the worth of your services are most often crossing a professional boundary, and I can almost guarantee you it won’t be the last line they cross. You’ve been warned, my dude.
Waiting to invest in education for my business.
I felt like I couldn’t spend money on expanding my knowledge. Google is free, YouTube is free. Why should I? I could go on and on about the free content I’ve scoured the internet for in an effort to continue learning about how to become a successful business owner, but I won’t bore you. What I will tell you though is that this year was the first year I invested in working with a coach one on one for my small business and it has been worth every penny thus far. I wish I would have done it sooner. It got me the answers I needed, I have an actionable plan of next steps to take to work towards my goals and I have peace of mind over the direction my business is heading in.
Many corporations allocate funds for continuing education for their employees. Shouldn’t we be doing the same for our businesses?
Investing in education for your small business isn’t wasteful. You can’t be a master of everything, it’s okay to need to ask for help! All this to say, if you’re lost and ready for some help and guidance in your business so you can have a clear roadmap to success, then it might be time to look into investing in coaching/a course for small business owners.
Oh, and did I mention I teach a LIVE cohort-style class for small business owners? That’s right, I do!
Not to toot my own horn, but if you’re reading this and you DON’T click the link below to learn more about how this course can change the game for you small business, then what are you even doing????
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