I never set out to be a small business owner, really. I initially took on some (what I later would realize was) freelance work from Craigslist gig postings—back when Craiglist wasn’t dripping with sketchiness—in an attempt to build up my portfolio with real client examples. A few jobs later, and I was hooked…and totally unprepared for being a small business owner.

For awhile, I did these gigs while still having a full-time job, so it just felt like ridiculously easy money and I was having quite the time getting paid for doing something I already enjoyed. But when a startup I was working at lost some funding and I was sent packing, I realized that I already had the beginnings of my own lucrative full-time job, if I was willing to put in some real elbow grease. So I dove in head first and started pulling in all of the work I could.

I say all of this to tell you that I certainly didn’t have all of my ducks in a row when “starting my business.” In fact, I was probably missing quite a few ducks when I haphazardly slapped together a small biz, making my fair share of mistakes in the process.

The top mistakes I've made as a small business owner—and what I learned from each

Here are a few of my favorites, each leading to lots of important lessons learned along the way.

#1 – Overextending myself

I used to be the queen of taking on every single project that came my way. At the core of this problem was a mix of not wanting to let anyone down, and also being afraid that more work may never come. And so I’d eagerly agree to just about any project at any time, squeezing new client after new client into my usually already over-booked schedule.

At some point though, I finally realized that this wasn’t sustainable; always being exhausted and working day and night really wasn’t that much fun. It took a big mental shift (that I still sometimes need a little reassurance with) to realize that, as long as I keep doing good work and market myself appropriately, new clients and projects will always come my way. So now, I’m no longer afraid to say no if I’m already booked up with other work, and I’ve found that about 75% of the time, most clients can wait until I’m freed up to do their project. The other 25%? They usually reach back out when they need something else in the future.

#2 – Not listening to my gut

After working for ourselves for a very short time, I think we all start to develop pretty good intuition about the people and projects that come our way. The problem most of us run into? Not listening to those gut instincts. For the longest time, I’d take on projects even though—deep down—I’d be getting a weird vibe about the person or the work. “It’s just me,” I’d tell myself time and time again.

It took probably five or six projects-gone-wrong for me to realize that every single time I sensed something was off, I was pretty darn right. I’ve since started listening and looking for any red flags or warning signs in initial meetings, phone calls, and emails with prospective clients. If I get the vibe that the relationship might not be the best fit for both sides, I’ll politely decline the project.

#3 – Not setting up project schedules

Raise your hand if you have a project that’s been lingering for months past the projected due date! (Boy, do I feel ya’ll with your hands up.) Up until pretty recently, I was a little too flexible with project deadlines. I trusted that the client and I would hit the ground running, and we’d wrap up a website in my projected three or so weeks. Never really happened that way. Of course, we’d hit the ground running on a new project, but once we got to a certain point—without fail—life would happen: kids would get sick, work would get busy, trips would be taken, etc.

These things that come up are 100% normal and I completely get that life continues to happen even while working on a new website. But, for the most part, these things can be predicted (minus the sick kiddos), and so I now ask website clients to agree to a project schedule. Just having this written structure and timeline in place truly resolves about 90% of the issues I was previously facing with never-ending projects. Now, if a client knows they can’t meet the deadlines, we revise the timeline and move their project to a time when they know they’ll be able to dedicate themselves to our project.

#4 – Not having formal contracts in place

Yep. I’m guilty of this one. Not really knowing where to begin and blindly trusting the clients who hired me, I worked without formal project contracts for a good while after first starting out. I was SO incredibly lucky to never have gotten terribly burned by not having a formal contract in place, but I knew it was only a matter of time before something really devastating happened. If you don’t have a contract yet? Get one now.

#5 – Being cheap

I’m a pretty frugal person in general, but with the money I was bringing in from my business, I found myself pretty relentlessly hoarding it. Rather than splurging on some extra tools or training to make my life easier and my business better, I’d squirrel every last penny away. Again, probably more afraid that work would be hard to come by in the future more than anything.

Recently, I’ve found myself more easily splurging on things that really make a difference like a good computer (sort of a must for my work!), a great backup solution, stock photos, training, etc. I’ve noticed that a lot of the smaller “splurges” make the biggest difference in my day-to-day business running.

Other small business owners out there: what are some silly things you did when you first started out? What have you been doing differently these days? Leave a comment below and let me know!