Three Fears Most Owners Share and How to Overcome Them

Business finances and emotions don’t often go together. But let me tell you, I’ve worked with over 70 owners at this point, and every single one of them has shared some type of emotional story with me. You see, business and money are emotionally charged topics. As owners, we pour our blood, sweat, tears, and sleepless nights into our businesses, and we don’t make big decisions lightly. 

When we talk about business finances, we have to remember that our mindset plays a big role in how we make heavy decisions. 

As a CFO, I often have clients ask if we can have an emergency call. I get to be their sounding board, uncover fears, and guide them toward a solid decision that will benefit their business. Here are three common fears clients call about and how we overcome them.

Discomfort with making hard decisions


Every owner has to get comfortable making hard decisions. If you are someone who tends to put off tough decisions, especially unpopular ones, this is going to be very difficult, but so worthwhile. 

During the lifetime of your business, you’ll probably have to do things like raise prices, fire employees, and make a stand for your moral and ethical lines. It’s important that you learn how to do this with careful thought, but without it pulling everything out of your soul. 


How do you get comfortable making hard decisions for your business?

Keep the big picture in focus. Remember that, while it’s hard to fire an employee, it’s really better for them not to be there. Often you’ll find the employee didn’t want to be there either, but they didn’t want the emotional drain of quitting. If you have to reduce pay, cut hours, increase fees with clients, and make other hard decisions, you’ll eventually find that it gets easier each time. You’ll see that, while these aren’t great things, they’re benefitting your business, and most of the time everyone understands and ends up in a better place. 



Fear of failure and missing out

I have struggled with this one myself. In the beginning, I took all kinds of clients because I thought I had to take every client who approached me. That’s FOMO (fear of missing out). At the time, I was afraid that if I didn’t take this client, I wasn’t ever going to get another one. (Spoiler alert—I kept getting discovery calls and new clients, so that fear was unfounded.) 

Lots of owners struggle with this because, as entrepreneurs, we are naturally visionaries and risk takers and we will jump at every opportunity.

How do you overcome fear of failure or missing out in your business?

It takes a lot of mindset work and outside feedback from someone who knows your finances to get comfortable missing out on an immediate opportunity for the sake of something better. Someone who knows your goals can keep you focused on your values and long-term vision, and over time, it gets easier not to get caught up in the immediate offer.

Just like it takes practice to make hard decisions, we have to practice holding the mindset of “We tried this, we thought it could work. It didn’t work, so we’re letting it go.”


It is such a skill to cut the cord quickly on something that is failing. A lot of the time, we want to tweak and adjust and try everything we can to make it work, whether it’s a service, employee, or system. But what I’ve found is, if we see the signs that something isn’t working out, we need to just stop whatever it is and move on. It’s a major skill financial leaders possess, and they learn it from practice. You can too.


Discomfort with standing out


Every successful business has to stand out in some way. It’s called differentiation, and it’s what makes your clients choose you instead of your competitors. Whatever that thing is, you have to let it shine somehow, some way. If your difference is that you only take 30 clients and you serve them really, really well, then stick with that. Let people know that. When you start to let that slip away and you accept more and more clients, you go against what makes you different, and you lose value. 


As financial leaders, we’re often scared to do that because we think it’s going to turn away clients. (Remember that fear of missing out?) But reality is that I, and most people, would rather work with someone who’s niche and skilled in an area where I need help than a jack of all trades. The uncomfortable part of being specialized and different and niche is that you do usually charge more. When we charge more, take fewer customers, and see fewer opportunities, it can introduce a lot of fear. 

How do you get comfortable looking different in your industry?


At AFS, we often get discovery calls from owners in the restaurant and retail industries, two industries that we don’t serve. Sometimes I try to convince myself I can serve them, but at the end of the day, I know it won’t really benefit me, and it definitely won’t benefit them. So I let those opportunities go. There are plenty of virtual CFOs who do serve those industries, but I specialize in construction, trades, and agencies, and that’s how I offer a high value to my clients. 


Again, the key here is to remember the big picture. Do you want to serve everyone kind of well? Or stick close to what makes you truly valuable and do it with excellence? If you hold to your niche, it will eventually help you grow. 


As a CFO, one of the main things I do for clients is listen and help them work through these mindset blocks so they can shape a business that supports their life instead of draining it. If you need a financial sounding board, please reach out! I’m happy to help (jen@assignedfinancialsolutions.com). 

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