19 Mistakes I’ve Made as a Small Business Owner (And Counting)

This post is embarrassing.

For me at least.

It’s a list of many of the mistakes I made over the past, oh, 20ish years starting and trying to start various businesses.

You may find some of these funny and laugh at me. I’m okay with that :).

You may recognize yourself in some of these.  

But if nothing else, I hope you can take from these and learn and avoid many of the mistakes I’ve made in the past.

So here we go (gulp), here are 19 mistakes I’ve made… (and counting).

1.      I thought I would be the exception

I remember hearing about how many businesses fail, how long things take to start, and all the other yada yada (or so it was in my mind) that people say about starting a business.

Yes, those stats apply to OTHER people and businesses, but not mine, obviously. I’m the exception. I’m going to be different.

Au contraire, Thomas, au contraire.

In case you were wondering: I was NOT the exception.

It’s easy for us to assume as humans that we are the exception, though. Daniel Kahneman talks about it in his book Thinking, Fast and Slow.

What you need to do instead is look at the base rates – the average – and take those as being realistic. However, you then can look at those who succeed or who beat the average, learn what they do differently, and apply what you can to succeed and do better.

You just can’t assume, like I did, that you will be the exception.


2.      I assumed people would just rush my doors and buy from me

mistakes small business owner expecting ppl to flood doors 1 1

I remember when I started one of my first businesses, I just expected the customers to come.  I just assumed people would buy.

When I put out the word, they would rush my doors and BEG me to sell my services and products.

It… well… didn’t quite work out that way.

I even joined the Chamber of Commerce and went to the networking meetings. I just knew by my being there people would see me and ask me to do videos for them.

Nope. Not quite.  

I even did an upgraded listing in the Yellow Pages – WHOO!_- (though I think they messed up my number), but it wouldn’t have mattered anyway.

Don’t get me wrong, I made some sales here and there, but people didn’t flock to me – just like I don’t flock to other people when they suddenly open a business, release a product, or make their name bold in the yellow pages (yes, this was a few years ago).

You can’t just expect people to show up just because you open up. It doesn’t work that way.

3.      Spent money on equipment instead of marketing

This was a dumb mistake.

When I started a video business years ago, I had a limited budget – along with all these grandiose ideas of what I could do if I had my own camera.

Now, some of the training I took on creating a video business specifically said “Focus your money on marketing, not equipment. You can always rent equipment for the projects you get.”

Did I listen?

Hahaha…. No. 

I wanted to do all those brilliant and creative projects I had in my mind.

So I had a nice camera and not a lot of money for marketing.

Not smart.

What I should have done is followed that advice and focused on marketing and focused on one area and did it well.

Then, over time, I could have worked on some of those grandiose ideas when I had cash flow rolling, but that’s not what I did.

And it hurt me.

4.      I lowballed my value

I’ve done this in a couple of ways.

First, I was often afraid to actually charge the value of what I was worth, especially with people I knew. And because I didn’t charge what I was worth, the value that others put on my work was what? What I charged – a lowballed figure.

At times I had feared too much that people wouldn’t pay what I should have charged, so I undercut myself. I believe now it was also a lack of self-confidence in myself and the worth I had.

Not smart.

Second, I sometimes tried to play the commodity game instead of the value game. Instead of building value and differentiating myself to justify the price, I tried to go low as I could go to seem “affordable”.

Also not smart of me.

5.      Making assumptions with employees and others

Assumptions are SO easy to make, and I’ve made way too many of them.

It can be easy for me to think that people will understand what I mean by X, that when I say I want this or that done, people will know what I mean.

I would tell someone “I want this done,” and then expect that what I’m thinking in my head is what they see in their head.

But usually, when I’ve done that, for some strange reason, the work I get isn’t what I expected.

And it wasn’t their fault.

It was mine.

I should have done a better job explaining and setting expectations and making sure what I’m trying to convey is what they are hearing.

I’ve wasted a lot of money and time with assumptions.

6.      I didn’t give clear expectations

(This is closely related to the above)

There have been times when I wanted someone to work on something – say social media. I would tell them to work on it, but I wasn’t clear on what my expectations were for it.

Or I would tell them I want this video edited, but I didn’t set the expectations for it of what the end result should look like.

So what happened?

Because I didn’t set clear expectations, what I got was what they thought my expectations were, not what they really were.

If I had taken the time to clearly state expectations, what the end result should look like, etc., then I would have been far better off.

7.      I hired too fast

There have been times when there was a lack, a need, and I wanted someone to fill that position. Having the position open created extra work for me or others, and I wanted it filled now.

Instead of taking the time to hire well, I hired fast.

And, when I hired fast, I found out quickly that I hired poorly.

And because I hired poorly, it created MORE work and frustration than if I had just taken the time to hire better.


8.      I didn’t take the time to explain how to do it better – I just fixed it

There have been times when I would delegate or give an assignment to someone, but for whatever reason, it didn’t come back like it needed to be.

The ideal action I should have taken is to show and teach the person the expected outcome or the steps they need to reach the outcome.

But that’s not always what I did.

I wanted it fixed. I wanted it right.

So instead of taking the time to teach or help the person understand what was wrong and show them how to do it better, there were times I just fixed it myself.

I then expected them to just see the difference.

That was dumb.

If I really wanted them to learn how to do it better, I should have shown them how and let them do it better.

9.      Let fear keep me from acting

Oh, this is painful.

I don’t know how many times in the past I let fear and the hesitation that comes with it keep me from acting.

I would sometimes overanalyze everything to a point, maybe go back and forth on the decision I know I should just make.

I don’t know where I would be or how many opportunities I missed because I let fear keep me from acting when I should.

10. Trying to do too much/Not focusing and doing one (or depending) a few things well

A few years back I was working on this site. The focus then was mostly general soft skills and helping people with their work skills in that (and that aspect is still here in ways – just expanded more to focus on leadership overall).

But I also had a site related to marriage that I was working on with someone.

And I also had another site related to raising kids.

And I was doing most of it by myself.

There’s nothing wrong, with the right team and people and systems in place, to own multiple businesses or run multiple sites.

However, again, it was mostly just me.

And I ended up stretching myself and not focusing on any one thing that I didn’t do any one of them well. I ended up quitting the other two and focusing on one (this site) so that I could give it the attention it needed.

Another way I’ve made this mistake is with social media and other types of marketing.

There are so many platforms and this “guru” and that “guru” saying you need to post this much or that much to be successful.

Instead of just focusing on one or a few, I have the propensity to try to do it ALL. Instead of doing one or a few well, I ended up stretching myself where I wasn’t really doing any well.

Again, it’s not wrong to post on all if you have the bandwidth, etc. But trying to do everything overwhelmed and stressed me and lowered the quality of what I did put out.  

11. Not turning off ads 😊

This was an “oops”.

My business partner and I were doing a webinar for an online course we were selling.

I set up Google ads and all the intro stuff to get people into the webinar. We spent a good bit of money (for us at that time) and had a few people come, but no sales.

Then I forgot to turn off the ads….

And I spent a bit more money for a webinar that was over.

Yeah, don’t do that. Remember to turn those things off :).

12. Expecting people to change even after evidence says otherwise

I believe that people do and can change. I think it’s good in general to give people chances to grow and do differently.

However, if a person keeps saying they are going to do something, but doesn’t do it, eventually that’s a sign.

The person I was working with wasn’t a bad person, but they were busy. They would commit to doing something (at least in my understanding), but then it wouldn’t happen or it would be really slow.

We would talk again, make more commitments.. and then the same thing would happen.

At that point I should have realized that it wasn’t going to change – but I kept wanting and hoping it would be different.

I don’t blame that person for not getting done what they said they would do – I blame myself because I should have realized that after the first couple of times, it’s not going to change.

13. Not focusing on value

The value you offer, and what makes you different, matters.

Offering the right value is what can make you stick out, set you apart, and make you a non-commodity.

When you have a great value and set yourself apart, you don’t have to play the pricing game. And, when you don’t play it, you can charge a higher or different price because you are unique.

You aren’t just competing with others based only on price.

However, there were times I didn’t do that.

I would just market something as just another general course or whatever it may be and expect it to stand out.

I would price it to beat competitors instead of adding the value and then pricing for the value.

I didn’t stand out because I didn’t offer better value.

14. I wasn’t constantly growing

As small business owners, we can get busy – really busy.

However, even in our busyness, if we want to grow our business, we must grow ourselves. We are the lid of our organization.

I know at different times in my business adventures, I went through periods without making the time to learn.

For example, at one point I was struggling with marketing – but I kept trying and failing instead of taking some of that time to invest and learn how to market better.

If I had taken more time to constantly learn and grow, I would have been more successful in what I did.  

15. Selling to everyone / not finding my niche

I don’t know if I can count how many times I’ve read and heard about the importance of niching down, building out an avatar, and knowing who you are specifically trying to target.

And with those times, I ignored or rushed through it too many times.

“My product can help everyone. Anyone can buy it!”

But even if that was true, you can’t sell to everyone. As the saying goes “the riches are in the niches”. You can target multiple niches over time, but targeting everyone is likely to make you hit no one.

When I’ve taken the time to get to know much more specifically who I’m targeting, their needs, problems, wants, etc., it helps me not only develop my product better, but it helps me with the words and copy I use as well as, and most importantly, helps me help them better as well.

16. Not embracing a growth mindset (not seeing mistakes as good; not embracing the fact that I’m going to stink at anything new that I start)

I knew about the growth mindset. I thought I had a growth mindset. I had even read Carol Dweck’s book!

But I really did not have a growth mentality.

I would see mistakes as failures of myself versus as what they are  – learning opportunities. I would even beat myself up over these mistakes instead of focusing on what they could teach me.  

I wouldn’t act at times because I feared failing – (which was stupid – because I would then fail because I didn’t act) – instead of seeing it as I should – again, as opportunities to learn and get better.

I also didn’t grasp at times the process of starting anything new – that you are going to do poorly at first, but just keep trying, putting it out, learning, and over time, you will get better.

It’s that way with any skill you learn.  

I would do socials or YouTube or whatever, and get frustrated because I wasn’t getting the results I wanted – instead of seeing it as that process of learning and every day getting a little better.

It would have saved me a lot of frustration (and I would have had a lot more growth in multiple ways) if I just had embraced the right mindset from the get-go.

17. I let negative feedback hold me back

I sometimes took feedback way too seriously and let it hold me back.

A business partner and I had worked on an online course that we were going to give away to colleges for their students.

I started messaging people about the possibility of using it – and one gave me negative feedback saying they teach their students differently about what we were offering.

I don’t know why, but I let that critique hit me way too hard.

Instead of just learning from it and moving forward (or making small adjustments for that one potential college), I let it defeat me and keep me from marketing it more like I should.

That wasn’t the only time, though. I can think of at least one other project during that same period where I let someone’s feedback affect me way too much.  

Please don’t make that mistake like I did.

Anything you do, someone will not like. You will get negative feedback.

It’s also easy to focus on that one negative feedback instead of the many other positives you may get (and even if all you get is a negative, that’s great feedback to learn from).

Just learn from it and push forward. See it as an opportunity for growth (and just realize sometimes some people are just going to be negative).

Don’t let negative feedback hold you back like I did.

18. Giving tasks to employees then completely letting go (e.g. abdicating)

Have you ever “known” not to do something but still ended up doing it?

Yeah, that was me.

I had hired some assistants to help with certain areas of the business. I was excited to have them.

I was working full-time at the time as well, so being able to let go of some tasks so I could focus on others was such a relief and blessing…

…except I let go a little too much.

I gave them the assignment and then didn’t really pay attention to what they did. I didn’t check to make sure they were on track and that expectations were being met.

I was just relieved not to have to worry about it anymore.

Not smart.

Then when things down the road didn’t turn out like I wanted, who was at fault?


If I had been wiser, I would have made the time to check in and make sure expectations were clear, they had the resources they needed, and that they were on the right path.

Instead, I didn’t get the results I wanted because I abdicated instead of delegating.

19. I chased after shiny objects

Have you ever got caught in chasing after shiny objects?

I know I have.

I would have a project I would be working on, or a course, or a type of marketing.

The thing with many of them, the idea was exciting, but the daily execution was often not. Some of it takes time and persistent effort.

Sometimes it can be a grind.

I would start pursuing one direction, and I may even make some progress, but then the excitement would fade, and then I would see something else that seemed like a great idea, so I would chase after that.

Or I would let my fear or insecurities of it failing make me jump ship before I brought something to completion.

It likely happened even more when progress was slow going (because some things take time).  

That was sad, and it held me back.

It’s not that you shouldn’t pursue new things, just be careful that you do it because it’s a wise thing to do, not just because it’s new and shiny.

Don’t make my mistakes

Those were some (though definitely not all) of the mistakes I’ve made as a small business owner/entrepreneur.

While these were embarrassing for me, I hope that if you recognize yourself in any of them, you can take comfort in the fact that you aren’t the only one.

I also hope you can learn from me so that maybe you can avoid some of the dumb mistakes I’ve made so you can make progress faster.

I’ll be extra honest here, too. I still can struggle with some of these. It’s an ongoing progress. Remember to always see it with a growth mindset and keep learning.  

Now to you: What mistakes have you made that you would share (if you feel so bold)? Let us know in the comments below.

Leave a Comment

Your email address will not be published. Required fields are marked *

Scroll to Top