My top 10 mistakes from 10 years in business

This month I’m celebrating 10 years in business! As you might imagine, I’ve made a LOT of mistakes over the past 10 years of running a creative business, so narrowing down to just 10 was actually pretty hard.

Like, really hard.

But mistakes are how you learn!

That’s why I’m also going to tell you what I learned and how you can avoid making the same mistakes.

Ready to count down my biggest screw-ups?

Let’s go!

10. Spreading myself too thin

If you’d visited my website between 2012-2014, You’d see that I was offering EVERYTHING I had any sort of skill or knowledge in, in the hopes that I’d have something that you would want to buy.

I offered logo design, print design, website design, SEO, general coding, illustrations, and social media management.

And my marketing? Blogging, Facebook page, Facebook groups, Twitter, Pinterest, Periscope… remember Periscope?! It was exhausting.

Not only was my messaging completely unclear (except for, “Please give me money, I’m desperate.”), but there was no way I could keep up with all of that as ONE person!

Back to 2015 again—when I started cutting down my offerings and where I was spending my time online, I started making more money. Why? Because I clarified my messaging and people finally knew what I did! Plus, I was able to get better at what I offered and where I marketed, because I was no longer trying to do too many things!

What I learned: It’s impossible for one person to be an expert in everything and to be on every social platform successfully. Narrow down to what’s really working.

9. Not having a support group

2015 was apparently a very pivotal year for me in many ways, as it was also the first year I started attending conferences and having a regular mastermind meeting.

I can’t stress enough how important it is to have business peers who can support you, offer feedback, and keep you motivated even when things suck.

I don’t know about you, but the people in my daily real life know nothing about running an online business, so having connections with other online business owners is absolutely crucial for me! I need people who get what it’s like to run an online business to bounce ideas and collaborate with. I can’t believe it took me so long to make real connections!

What I learned: As well meaning as family and friends can be, that doesn’t make them experts. Surround yourself with others who do similar work and have similar goals and you’ll succeed much faster.

8. Starting a personal brand

Okay, this one is definitely personal to me, and may not be a problem for you at all. But for me, having a personal brand was never going to work.

I had a business coach in 2014 (I think) that pushed me to have a personal brand. Well, of course she did, it was working for her. She wanted me to stop hiding behind my brand (EEF Designs) and step into the light and blah blah blah all that jazz.

And I get it, a personal brand gives you a ton of freedom to create things, you become known, and it works for lots of people.

But as someone who is extremely introverted and would rather just create things and then hide, a personal brand wasn’t the right move. I have never cared about being “famous” and TBH when I am recognized at conferences I get really sweaty and awkward.

I didn’t even like being the center of attention at my wedding! Why the heck would I want a personal brand?!

After several years of trying to make it work, in 2019 I rebranded to Successfully Simple which didn’t quite work for me, and then, of course, in 2022 I’ve just rebranded to Out of Office Entrepreneur.

My plan with this brand is to grow it beyond me, and to have more of a background role eventually. I love creating, teaching, and helping, but I don’t love the spotlight.

What I learned: A personal brand isn’t for everyone, and it’s not for me. Don’t try to force something that feels wrong.

7. Building the wrong business

I built the wrong business multiple times. I would start a business, start making money, and then realize that it wasn’t what I wanted.

A great example of this was my “subscription” box business that I started in 2012 when the idea was still new and very few box services existed. It was called Indie Giftbox, and I would source handmade items for a box I sold each month. It was a lot of fun, at first. I connected with a ton of artisans and featured them on my blog and inside the box. People LOVED the concept, and I didn’t actually have subscriptions–the box would just sell out in minutes every month.

But it was 2012-2013, and there weren’t all the options for running and managing subscription boxes that there are now. I had to contact each artist individually after hunting around on Etsy (I needed 10-20 artists per month to fill the boxes), negotiate prices with them, get them to ship me their stuff, store it all in my tiny apartment, blog about each artist, create a bundled box, ship it out, deal with any complaints or refunds, and I couldn’t scale past about 100 boxes per month.

At that time I was too new in business to even consider hiring help, and I had no idea about fulfillment centers.

I was spending 60 hours a week on this business, and between shipping costs and paying the artists, I was only making about $1,000/month.

The final straw for me was when I had a box release scheduled, but ended up attending a very unexpected funeral during it. There were too many orders for the website to handle at once, and the box was oversold. I had to scramble to work with 10 different artists to put together more boxes ASAP. And people still complained about the two-week delay on their boxes and tore me apart on subscription box forums despite knowing that I was at a funeral!

Today, I feel like I could have handled and scaled the business, but I was too much of a newbie back then, and hadn’t even considered what it would look like if the business was successful–an apartment stuffed full of things to ship, and a ton of time coordinating artists and time doing customer service.

I’d built a business that was, by all appearances successful, but that made me miserable. I ended up selling the entire business after about a year.

What I learned: Don’t just create a business that sounds fun. Consider what you want your life to look like first, then build a business around it.

6. Lack of confidence

My lack of confidence really held me back. I could have made Indie Gift Box work for me if I’d been more confident. I could have have hired help, found a fulfillment center, and let the business blow up… if I’d had the confidence to grow.

But because I wasn’t confident, I’d built a business that didn’t fit what I wanted (I did NOT want to hire anyone–terrifying!), and there wasn’t really anything I could do about it except sell.

Indie Giftbox isn’t the only example–I’ve let lack of confidence hold me back from raising my prices, launching courses, showing up online, and building a business that can really have an impact.

I think I’ve finally gotten over this, at least mostly. I KNOW now that I’ve taught thousands of students that my products are great, and that I should be sharing them with the world. But it’s something that I have to keep working at by taking the time to celebrate my accomplishments.

What I learned: I’m smart, talented, and I can do hard things. The same goes for you.

5. Not having solid systems

If you’ve been here for a hot minute, you know I LOVE systems and teach other creative entrepreneurs how to make their own.

But when I started my web design business, projects were a mess.

Back then there weren’t blog posts or companies all about creating systems–or if there were, they weren’t nearly as prevalent as they are today. I had no idea what a system even was!

Projects took forever, I was going back and forth with clients multiple times a day, multiple times a week! And wowowowow did I look unprofessional and like I had no idea what I was doing.

Of course, I was offering about 50 different things back then, so having a clear, repeatable, system was out of the question because every project was different.

Once I narrowed down my offerings, my systems fell into place, and I was able to start knocking out projects that used to take months in a matter of weeks. Now I can even do those same projects in a DAY.

With project systems in place I then started systematizing everything I could–which then led to automating most of my work, which has given me the 10-hour workweeks I now have!

What I learned: Systems speed up your work, enable you to automate a lot of your business, and can also allow you to outsource. If you don’t have systems, you need them.

4. Not establishing boundaries/office hours

As a recovering people-pleaser, this is still one I struggle with.

But back in the earlier days of my business, I had no boundaries at all–and I was okay with that! I was so excited to be working for myself that when the phone would ring at 7pm on a Friday night, I would jump to answer it.

That enthusiasm wore off pretty quickly. But by then, I’d trained my clients that I was ALWAYS available, and I NEEDED the money. So they’d call me on a Sunday morning with a “quick” question about how to change their personal Facebook profile picture (something not even related to what I was paid to do for them), and I felt like I had to drop what I was doing and take care of them, because I didn’t want to lose them as a client.

I’d also have clients adding me as friends on Facebook and DMing me, posting on my wall, and publicly freaking out if I didn’t respond to their question RIGHT AWAY. It was embarrassing, and hard to keep up with without a centralized place to manage communication.

This is how I ended up checking emails (and social media) at my wedding.

For years, I was checking my email all day every day (including right before bed), and was never able to go anywhere without internet access or fully relax, because I was always available for my clients. I felt obligated to accept their friend requests, and assist them wherever and whenever they needed help–even if it was something they weren’t paying me for!

But when I spent a month in the Amazon Rainforest and Galapagos islands, I HAD to log out. There’s no internet! And you know what? No one died.

After realizing that nothing in my business was truly THAT urgent, I was able to set and start enforcing boundaries in my business. I established office hours, as well as “available” hours–meaning when I was available to call. I then tightened that up even more, by switching to scheduled calls and only communicating via a project management system.

I even wrote it into my contract that blowing me up on social media was ground for immediate termination of our contract.

The really wild part? Almost all of my clients got onboard and didn’t seem to mind at all. In fact, a lot of them seemed to prefer the structure that my boundaries required! A few didn’t like it, and TBH, I ended up much happier without them as clients anyhow. I was able to fill their spots with respectful clients that I loved working with.

What I learned: Establishing boundaries and office hours in your business will allow you to actually log out, and your clients (at least the good ones) will respect you more.

3. Not using a contract

I don’t care who you’re working with, use a contract! I’ve done a few projects in the past without contracts, and almost every single one has blown up in my face. Without a contract you are asking for trouble. We’re talking scope creep, angry clients, ruined friendships or relationships.

The very worst no-contract project I’ll talk about in the next mistake, but a few examples where I’ve been burned by not using a contract:

• I did a swap with a brand designer where I made her a landing page, and in return she was supposed to design a brand. She ghosted me when the landing page was done.
• I did no fewer than 50 (really) designs for a coach who was never happy with what I came up with. I had charged her $150 because she was supposed to also recommend me as a web designer to her clients–I never got a single referral from her.
• A web design client kept coming back over and over and over for “small changes” that she thought should be included since she paid me $500 for a website… this was up to a YEAR later.
• A retainer client that I’d had for years (and let the contract lapse) left me because I was going on vacation–even though I had someone to cover me!

And I’ve heard of much, much worse situations from my students!

What I learned: ALWAYS use a contract. If you are not using contracts with every single client, PLEASE start!

2. Not listening to my gut

There have been lots of times I’d ignored my gut, and every time things have turned out badly. Today I’m telling you about the worst time. I’m going to try to keep this one short, but it’s an absolutely NIGHTMARE of a story that I could talk about all day.

In 2016 I’d had major emergency surgery and was still recovering when a friend of a friend got in touch. He’d allegedly landed a huge contract with a government agency to redo a bunch of websites, but didn’t know how to use WordPress, so needed to subcontract me.

He was going to pay me $350,000. THREE HUNDRED FIFTY THOUSAND DOLLARS.

But first we needed to knock out one website as a test, and get it rolling ASAP without getting bogged down by a contract.

Something felt sketch, but I was on medication that was messing me up, and he was a friend of a friend and everyone I knew kept telling me not to rock the boat and demand a contract, it would be FINE.

It was not fine. Every conversation was had over the phone so there was no written record, the websites were NOT just WordPress, but also Code Ignitor and a PHP nightmare. I ended up subcontracting out some of the work since PHP is not my thing. The guy was annoyed when I had to work with other clients who had booked me before he did, and told me that, “I hope going forward you’re going to focus on this project, or I might need to hire someone else,” so I started turning down other work. He lied to and manipulated me for months. He would say things like, “I know you’re a good, honest person, so we don’t need to have a contract.”

After spending four months on this project, I was out several thousand dollars that I had paid subcontractors, had turned down about $30,000 worth of other projects, and was at my wit’s end.

But the project was done. And I sent him an invoice. He, of course, then told me that he couldn’t pay me for the first website because he hadn’t been paid by the client yet. I, of course, had paid my subcontractors months before and was out several thousand dollars.

BUT! He had “proof” that he had submitted my hours to the client two days before and sent me a copy of the invoice he had allegedly sent two days prior. The kicker? It included 30 minutes of work I had done THAT MORNING.

I very nearly sent this asshole to collections, as it was almost a month later that he finally paid me. In the end I dealt with him for over 5.5 months, I made $7,000, missed out on $30k worth of other projects, and found out that he had NEVER landed the big contract he said he did, but had made about $100,000 off of my work on the one website.

What I learned: Go with your gut, no matter what anyone else says. And use a contract!

1. Letting others define my success

For a long time, I thought success looked a certain way. You see it all over the internet. Fancy cars, big houses, enough cash you can Scrooge McDuck it.

I wanted to be successful.

So I did what all the gurus were telling me to do. Buy this course. Create your own course. Sell a high-ticket service. Post 50 times a day on social media. Do this. Do that. Still not good enough.

This is a big part of what led me to spreading myself so thin, and being an inconsistent mess. I was trying to do what worked for others, not recognizing that I didn’t actually want what they had.

It took me a few years to sit down and figure out what I really wanted. What success looked like to me. It’s honestly a lot less fancy than what I thought it was. I don’t care about cars, I just want a reliable one. I care a little bit more about my house, but more about where it’s located than what it looks like. And I don’t want to make money for the sake of making money–I’d rather spend time playing with my kid, hiking, skiing, or traveling.

I don’t want a flashy life, I want a comfortable and fun one.

What I learned: YOU get to define what success looks like for you. Not anyone else. If you’re letting others define success for you, it’s time to get clear. Check out my workbook to help you define success for yourself!

Tl;dr:

I’ve made a lot of mistakes over the past 10 years. I’ve learned a TON from my mistakes, and while they definitely sucked, they were valuable lessons. I hope that you don’t have to make the same mistakes I did!