7 Mistakes I’ve Made Since Starting My Business

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Starting my business has been a great experience, but I’ve made mistakes along the way. Here are 7 common entrepreneurial mistakes and how to avoid them.

Starting our business is probably one of the best decisions we’ve ever made. For years I was limited by the belief that we couldn’t run a successful business or that I or we didn’t have what it takes to be entrepreneurs. It has been nearly five years since I quit my job and nearly seven since my wife left her job and the one thing that plays through my mind on a regular basis has been the same thought:

“Why didn’t we do this sooner?”

I suppose that’s a good problem to have, but it by no means communicates everything has been perfect over the course of our entrepreneurial career. We’ve made our share of mistakes since starting our business – some out of plain ignorance and others by sheer stupidity. With that in mind, here are seven mistakes we’ve made since starting our business. Hopefully, you can learn from them and avoid making them yourself if you’re considering going it on your own or are starting a new side hustle.

Getting too Comfortable


As humans, we crave comfort. When things are going well it’s easy to fall into the trap of complacency; things are going well, you don’t want to do anything to upset things, and you sit back to enjoy life.

There’s nothing wrong at all with enjoying life. I think it’s an essential part of having a good work/life balance, or at least some semblance of balance.

A small problem occurs when you play this comfort card to an extreme as an entrepreneur – you can lose your edge. That’s the last thing you want. You lose clients; you have an unexpected large expense or you have a big goal you’re struggling to hit.

You want to be able to adjust to do what’s needed to take care of any of those situations. Getting too comfortable makes it that much more difficult to accomplish. We’ve struggled with this at times, especially when things are going well and it can be a battle, at times, to find that right balance of not letting up too much on the gas pedal without getting lazy.

Not Focusing on My Email List


The money is in the list. That’s something we hear a lot as bloggers and one I summarily ignored the first few years of running Frugal Rules. I was getting email addresses, but I was doing very little with them.

I don’t know why I ignored my email list but it probably goes back to thinking it was just one more thing or that I wouldn’t benefit from growing my list – or that it was difficult. Now that I’ve been working on growing my list and actively engaging with readers I can confidently say all of those beliefs were wrong.

I use ConvertKit to manage my email list and it’s simple to use and has an easy to use interface, which is important to me…not being a tech genius. 🙂 Moral of the story, if you want to start a blog, the money is in the list!

Not Saying ‘No’ to Bad Clients


Remember the mistake of getting too comfortable? The opposite also holds true, especially when you’re just starting out or fear you won’t have enough business. Even though we’ve been running our business for 5+ years, it always plays out the same way.

We get a client but something just doesn’t feel right about the situation. It could be about the client themselves; it could be about the pay or something else, something just doesn’t feel right. In spite of that feeling we march on doing work for them – often against our best judgment.

Without fail, at the end of the situation we ask ourselves why on earth we agreed to work with the client. Sometimes it may come down to not wanting to say ‘No’ to the client or uncertainty about the amount of work we have. The important thing you need to watch out for is that it doesn’t cause you to compromise your values and take on work that goes against what you stand for. We’ve not done that, but it can be tempting in the right situation.

Not Unplugging


Unplugging isn’t a need specific to entrepreneurs. We’re in a society that seems to have smartphones surgically attached to our hands (and with VR, soon our heads).

It can be worse when you run your own business. Clients can get ahold of you 24 hours a day, during the holidays and more. Things come up, of course, but it’s important to set boundaries. The more you give, the more a client will expect and then you only have yourself to blame.

We’ve run into this issue with clients, and have fed it ourselves, but you need to set expectations early on in your relationship to make sure everyone understands what’s expected. Ultimately, I want to control my time otherwise what’s the point of working for myself if I and we can’t enjoy the freedom it affords?

Not Trying New Things


This goes along with the comfort angle. As a business owner, heck as a person in general, you need to grow – professionally and personally. Not that you should always be actively on the lookout to challenge yourself, but you need to at least have your eyes open to opportunities and challenges that will benefit you.

Not everything new you try will be a wild success. Most will likely be failures, but they provide invaluable lessons you can use for the next situation. That is where growth comes from and God only knows where that growth will take you – this is something I struggle to remind myself of on a regular basis.

Trying to do Everything Myself


Raise your hand if you like to try and do everything yourself. I’m incredibly guilty of this mistake and so much of it comes down to trust. We think we’re the only ones who know how to do “X” and just add it to the pile of things to do.

Here’s the rub, and I we don’t like to admit it – we don’t know everything and, worse yet, there’s only so much time in the day. So, either you’re going to be a zombie because you don’t get any sleep or things are going to fall by the wayside, neither of which is good.

It wasn’t until we started hiring out things we either didn’t know how to do or didn’t want to do that more opportunities took place. It’s quite simple – hiring out certain tasks allows you, or should allow you, to focus on things you want to focus on and focus on your higher-level goals.

As the saying goes, you need to spend money to make money – just be wise about it and it can be a great way to grow your business. You’re only as good as the team around you, so take hiring out tasks seriously and you’ll be amazed at the growth you’ll see in time.

Starting my business has been a great experience, but I’ve made mistakes along the way. Here are 7 common entrepreneurial mistakes and how to avoid them.

Isolating Myself


I’m an introvert by nature. I get overwhelmed by large crowds (they make me mentally tired), so working for myself on the Internet plays well into my drawbacks. The isolation may be great for my introverted nature, but it does little for the growth of our business.

Like a true introvert, I can go days without interacting with a lot of people, but the camaraderie is something I miss from my day job – at times. This is something I still struggle with at times, but it’s important to find avenues to get some sort of interaction with others.

Whether it is getting a co-working space, meeting with friends or business partners on a regular basis or simply going out to a coffee shop once a week, find something that works for you and helps you not be as isolated. Like the hiring a good team around you above, getting out there and meeting with others can help you grow both personally and professionally.


If you work for yourself, what’s one mistake you’ve made in the past? When did you hire your first employee or contractor? How hard is it for you to say ‘No’ to clients?

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John is the founder of Frugal Rules, a dad, husband and veteran of the financial services industry whose writing has been featured in Forbes, CNBC, Yahoo Finance and more.

Passionate about helping people learn from his mistakes, John shares financial tools and tips to help you enjoy the freedom that comes from living frugally. One of his favorite tools is Personal Capital , which he used to plan for retirement and keep track of his finances in less than 15 minutes each month.

Another one of John's passions is helping people save $80 per month by axing their expensive cable subscriptions and replacing them with more affordable ones, like Hulu with Live TV.


  • One thing I’ve really struggled with when I’ve tried to scale my side hustles is trying to do everything myself. It can be difficult to hand the reins to someone else even on small tasks, because you have to be okay with it not being done exactly how you want. Easier said than done!

    • That’s something I still continue to struggle with myself – even though I know I shouldn’t. You’re exactly right DC, so much of it comes down to being ok with things not being done exactly how you want them done. I think it, so often, comes down to knowing you’re not perfect so it’s ok to let someone else in – because, you never know, they may be able to do something better.

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