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Top 10 Pros and Cons of Owning a Small Business

By December 8, 2022Business, Taxes

You could have an entire panel of people talking about the pros and cons of owning a small business and get hundreds of different reasons. I’ll just share with you some of the first ones that come to mind.


PRO – Set Your Own Schedule


First pro I think, is that you get to set your own schedule. Now, at the same time, I think we need to understand that the con, the other side of that coin, is that if you’re not careful, even though you set your own schedule, you will not have freedom of time.

A lot of times when someone transitions from working for somebody to working for themselves without proper boundaries in place, you basically become a slave to all the things that need to get done. Because you’re not taking the time to think through how you actually want to grow the business. You’re so busy going from one task to the next, you end up burning out and working 85 to 100 hours a week. So yeah, you can set your own schedule, but in order to have freedom of time, you have to make a conscious effort to do that.

And as a business owner, as long as you make a conscious effort, setting your own schedule can be a pro. You’ll finally get that freedom of time that you’ve been hoping for. Which honestly, for a lot of our clients I’ve dealt with, freedom of time is probably one of the top reasons they chose business ownership. But of course, we’ve seen a lot of those clients not actually enjoy that without some help.


PRO – You Made it Happen


You are ultimately responsible for your business, both successes and failures. This can be either a pro or a con.

I think this is something that actually applies to everyone in the world, not just business owners. I feel it’s healthier to adopt a mindset that you control your success and failure. If there’s a failure, it’s something that you did that you can improve and control. I don’t think it’s healthy to pretend to be a victim. I am not talking about scenarios from a legal standpoint where someone is literally a victim of horrendous crimes. I’m talking about playing the victim by thinking you didn’t reap many successes when you put little work or effort into it in the first place.

You’re to blame can be a pro or a con, but I personally like it. I like knowing that if something isn’t going well, I can sit down and take an objective view and determine what it is that I can do to make it better.


PRO – Dream Team


Another pro is you get to choose who you work with. It’s your company, you choose who to hire. So that’s fun.


PRO – Work on What You Want


You also get to choose the type of work that you do. You know, if you’re working for someone else, you’re being paid to do that one thing or whatever it is that they’re asking you to do. And in order to keep getting your paycheck, you kind of have to keep doing that.

If it’s your business, you get to choose the work that you want to do, and sometimes more importantly, you get to choose the work that you don’t want to do. And then pay someone else to do it for you. That’s really nice.


PRO – Tax Benefits


The tax code is a lot better for people as business owners than it is if you’re just a W2 employee. The tax code has a lot more options for business owners to save on taxes. Checkout our Big Sexy Beefy Tax Crushing Packet for some of the ways you can save thousands on taxes as a business owner.  


PRO – Improving Others Lives


I personally get a lot of satisfaction knowing that I am blessing the lives of my team. It’s been fun to know that I am responsible for making a handful of my team members millionaires. That’s really cool. So there’s additional satisfaction that comes, not just from growing your business for yourself, but also growing and helping the lives of your team members.


PRO – Sellable Asset


Another possible pro is, it’s an asset that you’re building. So someday you could choose to sell your business. Now I’m not going to get into it here, but you have to be conscious about how you’re growing your business so that it is worth something when you sell it. Too many business owners think they’re just going to sell the business, but they haven’t created their business in a way that makes it very sellable. Always look for guidance on building your business into a sellable asset.


CON – You’re an Island


You are going to feel like you’re on an island as the owner. There are certain things that are frustrating and difficult to deal with that you can’t talk to your team about because they’re always going to view you as the owner. If you’re complaining about something to them, it’s like boohoo. Most people think because you’re a business owner, you make way more money than you actually do.

But you’re on an island. There are certain things you can’t talk to your team about. There are solutions, though. One example is I am part of a mastermind group with other seven figure plus business owners. We can talk about some of these frustrations and work through them.


CON – Incompetence


Here’s an interesting thing. It’s going to sound weird, but you are always going to be the most incompetent person in your business. That’s more so true if your business is continuing to grow. Because here’s the reality. When I first started my business, I didn’t know how to run a $300,000 accounting firm, and then we became a $300,000 accounting firm. Cool, now I know how to do that, but then we grew to $700,000. Well, I’ve never ran a $700,000 accounting firm before. I don’t know what needs to happen. You go through these different stages of business because honestly, what gets you to $1 million is not what gets you to $5 million or $10 million. There’s these kind of stepping stones as you grow your business.

So as the owner, the CEO, the President, you’re always going to be in a position that you’ve never been in before. You can help your team become more competent in their job. Like for us, we do a lot of tax returns and a lot of bookkeeping. If we’re a $10 million dollar company, it doesn’t really matter to the team member as much as far as their daily tasks go, because like in our case, they’re still doing tax returns and bookkeeping.

You will always be the most incompetent person in your business. Make sure you have the fortitude and acceptance that that is the case and that you might make mistakes. Remember you have the control to shift and learn from your mistakes and still improve your business regardless. Don’t let that uncertainty or self-doubt in your position as the owner of a company that you’ve never ran before at that size, cripple you or put you in handcuffs. Make decisions. Do the best with what you got and make a choice. You’ll find out after whether if was a good or bad decision and then respond accordingly.


CON – Bad Apples


The larger your team gets, the more likely you’re going to have some team members where whatever you do, however generous you want to be, it’ll never be enough. And that can be really frustrating, especially when you’re someone like me who takes business very personally. I want my team members to have a good culture and work environment, but sometimes it’s just not enough.

They’re like, oh, you want me to do this one extra thing? Okay, well, how much more money are you going to pay me because of that?

Never mind that they’re already currently well paid and have a really tremendous career path here that will pay them more than anything they could ever imagine. There’s kind of this tit for tat type of thing, and it can get frustrating sometimes. It feels like you’re expected as the owner to be super generous all the time. It’s more frustrating because you are trying to be generous and you put stuff out there, but sometimes you don’t get something back. Balancing that emotionally can be tough.


You’ll notice the cons are mainly mental and emotional stresses that aren’t really talked about that much when discussing the pros and cons of owning a small business. But being aware of them, expecting them, and preparing as much as possible for them will make all the difference in having a positive ownership experience.

Now’s the perfect time to pay someone to do some of that work you hate doing, like bookkeeping and tax filing. Take that stress off your plate and get more of your time back. Schedule a no obligation call now and set next year up right.









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