Destructive Habits of Business Owners • Financially Simple

I’ve often acknowledged that business owners are some of the hardest-working people on the planet. You have so many responsibilities, for yourself, your family, your team, your clients, vendors, etc. But in the midst of these responsibilities, you will undoubtedly encounter problems. So, you approach each day seeking to solve these problems (often, before they even occur) to continue pushing the business forward. And yet, there’s a pervasive habit that, if left unchecked, could destroy the very thing you’ve worked so hard to build. Let’s explore this habit of self-sabotage that so many business owners struggle with.


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  • How we bend our values and goals to pursue immediate gratification
  • The negative mindset, how self-sabotage stems from it, and how to reframe it
  • My love for pizza and the difference between conscious and unconscious self-sabotage
  • Finding the roots of self-sabotage
  • How fear triggers self-sabotage
  • Impostor syndrome and how it detriments our chance of success
  • The common forms of self-sabotage
  • Perfectionism and how it leads us to self-sabotage
  • Celebrating small victories and other ways to combat impostor syndrome
  • Why micromanaging and not asking for help is self-sabotage
  • The importance of continuing education

Self Sabotage: What Is It?

I work with a lot of business owners. I’ve been a business owner, myself. Because of this, I’ve worked exhaustively to understand how business owners think. It’s fascinating to me to understand the differences between the mindset of an entrepreneur and their employees. But there’s a difference in thinking, even in the business space, between entrepreneurs and managers. As I’ve grown to have a greater understanding of the business owner’s mind, I’ve also noticed that you’re prone to getting in your own way. But what is self-sabotage?

Well, self-sabotage occurs when you destroy yourself physically, mentally, or emotionally or deliberately hinder your own success and wellbeing by undermining personal goals and values. I like to think of it as having the angel on one shoulder and the devil on the other. You know what you ought to do because the angel is whispering in your ear. However, oftentimes, business owners ignore this wisdom and end up harming themselves. It is a profound and universal position that stems from a negative mindset. You see, when you’re thinking correctly — with an abundance mindset — you’re less likely to harm yourself.

I was just speaking with a business owner about a meeting between his company’s executives. As they were discussing one of their initiatives, one of the execs said, “We can’t do that.” I stopped this business owner in the middle of his story to reveal the negative and self-destructive nature of such a statement. Whenever you say, “We can’t,” or “There’s no way,” that’s a negative statement, and it halts all rational and creative thinking to figure out a way to make it happen. Instead of opportunities, such statements breed a mindset of complacency and impossibility.

Conscious or Unconscious

Self-sabotage can be conscious or unconscious in nature. You’re not always going to be aware that you’re self-sabotaging. On the other hand, there are moments when you’ll be well aware of what you’re doing. For example, if I decided that I needed to lose 15-pounds, but then sat down and ate an entire pizza by myself, that’s an example of conscious self-sabotage. I know beforehand that eating that pizza will prevent me from reaching my goal of losing 15 lbs. By the way, stop judging me. You know you’ve thought about eating a whole pizza before, too.

On the other hand, an example of unconscious self-sabotage could be procrastinating the start of a big project. You know you need to do it, but for some reason or another, you just keep putting it off. This is unconsciously sabotaging your efforts because, although you’re choosing to put off the start of the project, you’re not necessarily aware that the decision to do so could result in a negative outcome.

Common Ways Business Owners Self Sabotage

There are many different ways you could sabotage yourself. You may not relate to each of these, but if you’re honest with yourself, you can probably relate to at least one of these common forms of sabotage. So, without further ado, let’s explore a few ways business owners can disrupt their own success.

Perfectionism

Believe it or not, perfectionism can really throw a wrench in the pursuit of your goals. You’ve probably heard the old adage, don’t let perfection be the enemy of good. Self-sabotaging is exactly what that statement is referring to. When perfection is your standard, it becomes very easy to get tangled up in the minutia that you’re making no progress toward your goal.

Rather than working to perfect one small detail, business owners must be willing to step back and make changes that will positively impact the entirety of the business. There are just too many moving parts within a business to seek perfection. Instead, the goal should be to achieve a good — or what I call best-in-class — movement.

Not long ago, I was speaking with a business owner about putting a process in place. I asked how he would measure the success of the process. He responded with confidence, “Well, we need to have 100% participation and a 100% success rate in (this particular) measurement.” I laughed to myself and told him that he’s already set himself up to fail. You see, there’s rarely a scenario in business where you can achieve 100% of anything.

Imposter Syndrome

Now, I’ve written an entire blog on this subject in the past, but imposter syndrome is often a form of self-sabotage. Not only is it more common than you might think, but it destroys any chance for success simply because you don’t believe you’ve earned it or deserve it. Chances are, you’ve never been in the position you’re in before. Despite this, you must convince yourself that you can handle it. While you’re convincing yourself, you must also put on an air of confidence so that your team, customers, and even other business owners believe that you have all the answers.

There’s some good-ish news though. You’re not on this journey alone. There are millions of business owners dealing with imposter syndrome. I know the fear of being “unmasked,” but it’s irrational and invalid. Why? The majority of people are too consumed with their own self-doubts to worry about uncovering yours. So, how do you combat self-sabotaging through imposter syndrome?

One of my favorite methods is to simply celebrate the small victories. When we do something as a family, I always ask my middle son, “What did you like about today?” You see, he tends to over-analyze everything which leads to focusing on the negative aspects. I know this about him, so, I make it a point to ask what he likes about any given situation. We’ve been doing this for a while and I’ve noticed that the imposter syndrome he struggles with has begun to subside because he’s now celebrating the small victories.

Micro-Management

One thing many business owners struggle with is trying to spin all the plates. You have things you’re really good at and enjoy doing, like everyone else. However, you also have things you just hate doing (like everyone else) that your business wouldn’t exist if they didn’t get done. For me, it’s paperwork. I loathe paperwork. Friends, I would rather hammer nails into my eyes than fill out paperwork. Does that mean I can’t do it? Not at all. I’m also more detailed than many when it comes to completing paperwork. But it would be to the detriment of the business if I held onto that task to guarantee perfection. How so?

First, your skills and talents can be used in other areas of your business. You could keep spinning the plates but other areas will suffer if you do. Instead of trying to handle the items you don’t excel at or don’t enjoy doing, you must hire a team that you can trust with handling these tasks. Second, if you’re to decentralize yourself from the business so it can one day be sold, you’re going to have to relinquish some of the tasks that you are highly skilled at. So, micro-managing every detail of your business limits how far you can go; either by spending time on tasks that you’re not well suited for or by spinning all of the plates on your own so the business can’t be transferred.

Neglecting the Importance of Continued Education

We live in a society that is stuck in rapid growth mode. If you’re too busy working on small details or handling the daily operations to continue learning about the latest trends and developments in your industry, you’re going to fall behind the competition. It’s that simple, folks. Unless you’re educating yourself and being challenged by several people, you’re self-sabotaging. How do you avoid this?

Look at your calendar for the year. Find a time to block off where you can attend a continued education event. This could be a weekend seminar, an industry conference, or even a course curriculum at your local community college. Whatever it is, continuing education is vital to staying competitive in today’s business world.

Waiting to Strike

I love deep sea fishing. Not long ago, I was on a trip where we were throwing some top-water lures at some mahi-mahi. I watched as they would circle around, deciding whether to take the bait. Inevitably, another fish would come in and snatch the bait. Thus, the first fish waited to strike and missed their opportunity. Now, in this case, they were missing the chance to get hooked on a line, but it’s the same principle. I see so many business owners presented with an opportunity and they just circle around it until someone else snatches it up.

Obviously, you want to make calculated decisions in business, but eventually, you’ll succumb to paralysis by analysis if you don’t just go for it. Things move quickly in business. You have to act quickly or the opportunity will pass you by. That’s why you must posture yourself with systems and operations to be able to make quick, rational, and productive decisions. Position yourself to be proactive, rather than reactive. Self-sabotage happens in business, all the time. Where, as a business owner, are you prone to sabotage yourself? What are you going to do to prevent yourself from doing so?

Wrapping Up…

Friends, life is hard. But life is good. Operating a business can be frustrating, but it doesn’t need to be. Understanding where you’re prone to self-sabotage can enable you to avoid setting traps so you can make things at least financially simple. Hey, let’s go out and make it a great day!

Where are you prone to sabotage? Do you have a plan in place to prevent it from happening? If not, reach out to us. Our team helps business owners with things like this on a daily basis. We’d love to meet with you!

Justin Goodbread

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