30 Things I’ve Learned in 3 Years as a Creative Business Owner

I’ve officially been a creative business owner for 3 years!!! (the multiple exclamation points are absolutely necessary). Some days it feels like I jumped into entrepreneurship only yesterday, while others it feels like I’ve been living a dream for years. Which it is a dream, and it’s an accomplishment I’m really freaking proud of—especially since so many small businesses fail within the first few years.

Like many of you have, I followed the pretty standard path of graduating college and heading straight into the corporate world. I started my first job weeks after graduating and was promoted within 6 months. Yes, work ethic had a thing or 2 to do with it but it was also to get me to a specific title level so I could work more hours—not as glamorous.

After a few years, I started a new position with a different company and had what many people called a dream job. I was planning corporate incentive travel for our sponsors and going to places like Napa Valley, Puerto Rico, Las Vegas, the British Virgin Islands, etc for week-long trips.

Ya, dream job described it pretty well! But I was young and naive at the time and no matter how grateful I was for the opportunity, I don’t think I realized the magnitude of what I was doing. Or the amount of trust the executive staff had to have in me in planning $500k+ trips and events all over, at the ripe age of 25, maybe 26 at the time.

It sparked my love even more for marketing and events, so I transitioned into a new role and company that amplified things from a few trips a year to 70-80+ events a year. It was great until it wasn’t—but that’s a story for another day!

I was ready for a new chapter so I headed out west to Denver, CO. I had family living there so it was comforting to have people there to show me the ropes. It also never got old walking out of Target or the grocery store and seeing the mountains.

After a few months of taking in the new landscape, I started what I called my dream job overseeing social media strategy for a national hospitality company. I loved it and everyone I worked with.

And then March of 2020 came and the world as we knew it completely changed. I was furloughed, brought back, and eventually, my position was eliminated like many of you may have experienced.

I was crushed.

Not knowing what to do next, I figured I’d try freelancing. I had talked to my family about it and my former boss so I felt pretty confident that I’d be able to get some work here and there until things settled down (oh so naive once again).

Being the overachiever I am, I wanted to make things officially official so I filed an LLC, got a business bank account set up, built my website, etc, etc, and launched The SM Collective. Now 3 years later, this idea to get me through the unknowns going on in the world has turned into a fully-functioning creative business that serves clients worldwide.

THIS is my dream job.

3 years into the business, I’ve learned a lot—A LOT!!! I could probably write a book about all of the things I’ve learned. But you’re a busy creative business owner, too, so I’ve narrowed it down to 30 of the top things I’ve learned these last 3 years. It’s lessons learned and tips for creative entrepreneurs all rolled into one!

So in no particular order, let’s dive in!

1. You will fail, more than once. And it will suck. But you’ll only come back stronger and learn from your mistakes, both big and small. No, this isn’t some cliche saying, it’s just part of being a creative business owner (and part of life). If a creative business owner says they haven’t failed, they’re lying to you.
2. The flexibility is *chef’s kiss.* It’s an unmatched perk the corporate world just can’t compete with on any level. Want to go for a run in the morning and then have coffee and breakfast with your Grandma? No problem. Is it that time of the month and your brain and body just aren’t having it. No worries, close the laptop, the emails will still be there tomorrow. Need a mental health day to recharge those creative juices? You got it, the right clients will understand. Work best early in the morning, or maybe you’re on a roll late at night. Perfect—find your groove and what works for you.
3. Schedule your emails to clients. I work with clients all over the world, from Hawaii to California, Colorado, New York, Pennsylvania, Minnesota, Australia, and beyond. Aka, most of my clients are in very different timezones. And no one wants to get an email at 11pm or 3am. I always schedule my emails to send to clients during normal business hours based on their timezone.
4. Being a creative business owner is like riding a never-ending roller coaster ride. Enjoy the highs and toot your own horn, and take deep breaths through the lows.
5. Done is better than perfect. I’m still working on this on, TBH. Perfection doesn’t exist so aiming for perfection is essentially setting yourself up to fail. So I repeat, done is better than perfect.
6. Don’t overthink things and go with your gut. I found files from my first few months in business as I was transferring things off an old laptop. I was shocked at how aligned and good some of the stuff was—definitely did not give myself enough credit. Even as my business has shifted over the years, my gut always knows what’s right.
7. Along the same lines, don’t rush things. I preemptively jumped the gun on a few things in year 2 of business. I don’t regret them, I just wish I would have taken more time to fully flush things out, prioritize, and focus on what was good for me and my business, not what everyone else was doing and accomplishing.
8. And tagging off of that, stay in your lane. FOMO is real and it can suck you in when you least expect it and make you do crazy things. Okay, maybe that’s a bit aggressive but still, you get the point. Do what you want in your creative business when you want to and how you want to. Who cares what everyone else is doing.
9. Don’t use Flodesk forms on Pinterest. Instead, create landing pages on your own website so that you get the website traffic. I was naive (once again) and enjoying the “shiny object syndrome” of Flodesk and how easy it was to create a “landing page” that my SEO-obsessed self completely skipped over that part (I know, I’m embarrassed for myself—but hey, lesson learned).
10. SEO, SEO, SEO. Yes, I’m an SEO strategist that offers done-for-you SEO services and white label SEO for designers and copywriters and I’ll probably have “find me on Google” on my tombstone. But please, please, please…prioritize SEO. Yes, SEO is more of a long game than social media. But with social media, the lifespan of a post is maybe 24 hours. With SEO, the pages of your website and your blog posts can drive traffic for years and years and years. I dabbled into lifestyle blogging back in the day on the side and I still to this day get affiliate income from blog posts I wrote 5-8 years ago. That’s the power of SEO.
11. And tagging off of that, prioritize blogging and email marketing—in that order, please and thank you. Once you have enough content on your blog, then you can add Pinterest to the list.
12. Hire someone to do your taxes for you. I did my taxes myself my first 2 years in business but this last year, I wanted absolutely nothing to do with it. It was great getting to understand it a bit but it’s not my zone of genius. If you’re in the Central NY area like me, I highly recommend Terzolo Financial Group—Ed and Shelley (husband and wife duo) are just the nicest people. (As a sub-lesson to this, set up a business 401k—you can thank me later.)
13. Speaking of taxes, make sure you save for taxes and pay quarterly tax payments, both state and federal). I started following the Profit First method of accounting for my biz very early on which makes this so easy to do.
14. Your mental and physical health is a priority over everything. If you’re not at your best, you can’t provide the best for your clients. Take care of yourself. Don’t forget to eat lunch. And to drink water throughout the day.
15. Burnout is real and hustle culture is overrated. If you’re wondering if you’re burnt out, you probably are. Take some you time—your mind, body, business, and clients will thank you.
16. The limit does not exist on your financial freedom. Having your own business is the sweetest money you’ll ever make. Nothing can compare and no cushy corporate salary can compete. But make your own goals. There’s so much more to being a creative business owner than hitting $10k, $20k, $50k, whatever dollar value months. And enjoy it—the big and little things. From treating myself to Starbucks after a crappy night’s sleep, to traveling for a couple of weeks at a time, to buying my first home, or to even having to unexpectedly have to buy a new vehicle because mine turned into a boat (I’ll probably make this a story in my weekly newsletter soon). Taking a step back to realize that my business allowed me these opportunities is something I will never, ever, ever take for granted (and it’s really freaking awesome!!!).
17. Learn your work groove and/or zone and lean into it. Cutting the corporate world cord of working 9-5 (let’s be honest though, a 9-5 is never really just a 9-5), being afraid to get up to pee, eating lunch at your desk, not being able to wear both earbuds…it is hard to cut some of those habits. But back to some of the earlier lessons about flexibility and freedom, find what works for you. Do you work best in the mornings? Great, wake up before the sun and get the most important tasks done first. Do calls drain you energetically? No problem, protect your schedule like a hawk and only take calls on specific days within a specific window of time. Do you need music playing while you work? Great, find a style and playlist that works for you. Do you need frequent breaks creatively and energetically, or maybe for your eyes and head from staring at a computer all day? Set a timer and walk away from your computer (and phone) during your breaks. Scrolling Instagram on your break time is NOT a break.
18. BOUNDARIES. Bold, underline, italicize, and highlight, all of the things. Clients will respect you more AND you’ll feel more at ease and balanced.
19. Tagging off of that, it’s okay to say no or to push back. You’re in the drivers seat. You can say no to things that don’t align. No to red flag clients. No to doing tasks that aren’t part of the project scope.
20. Community is everything. Working from home by yourself can get lonely pretty quickly. Find your people and love them hard. I’ve prioritized collaborating with other designers and copywriters this year on projects and it’s been SO good for the soul. I’ve met so many great people AND it gives that teamwork feel without having to “scale to an agency model” the so-called biz coaches preach about.
21. No platform is perfect. Whether it’s your website platform, email marketing platform, CRM platform, etc etc etc…they’ll all have pros and cons to them. Find what works for you and your creative business and for your processes. You don’t have to use something just because everyone else seems to be using it.
22. Instagram is a highlight reel. Don’t compare your day/month/week/year/biz/revenue/clients or anything to what you see on the gram…they go through lows too (you just don’t see it).
23. $10k months aren’t the end-all-be-all. There’s so much more to entrepreneurship and being a business owner than hitting a specific revenue marker designed and marketed by some random person you don’t even know.
24. Also, niching down isn’t everything either. You absolutely can and there’s nothing wrong with it, but also don’t feel like you have to.
25. Consistency is key. Whether it’s posting on social media, blogging, or updating your website, be consistent with it—even when it sucks, even when engagement is low, even when pageviews are low, and even when algorithms are changing. So I repeat, be consistent (still working on this one on the social media side…one day I’ll get there).
26. It’s okay to make big pivots and shifts. No explanation is needed.
27. You don’t need to invest in a full brand photo shoot at a studio that ends up looking like every other brand shoot on the market (IMO). I’ve yet to invest in brand photos. Do I want to? Yes! Are brand photos powerful? Yup! I just haven’t felt called to…and that’s okay! I’ve made it this far with stock photography and self-timer photos, and I’m A-okay with that.
28. Prioritize working ON your biz, not just IN your biz. Dedicated a day each week to working on your own business…be it creating social content, blog content, scheduling Pins for Pinterest on Tailwind, optimizing your website, writing your weekly newsletter, furthering your education with courses, checking in on your biz finances, the list goes on.
29. Be you wholeheartedly. You won’t be everyone’s cup of tea and that’s okay! But when you’re you to the core, those dream clients will be able to spot you from a mile away.
30. To-do lists are great (I love lists). But don’t make your to-do lists so outrageous that you end up feeling like you failed because you “only” accomplished 3 of the 26 things you had on your list for the day. Keep your list to 3 tasks, 5 at the verrrrryyy most.

And there you have it, 30 key lessons and business tips for creative entrepreneurs that I learned in my first 3 years in business. There are certainly pleeeeeenty more but these ones I feel are the most powerful.