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If you want to succeed in business, stop being an imposter.

Dustin Slightham
Dustin Slightham
8 min read
If you want to succeed in business, stop being an imposter.

I haven’t always been an entrepreneur and an owner of a small business. In my early corporate life, I was the manager of a 200+ person team for a Fortune 500 company. We were a Six Sigma organization, which meant we strived for near perfection—constantly evolving and manipulating our processes to be better than the previous iteration.

Life was good. I was living the hustle and providing for my family.

But then…I had a kid.

Eighty hour work weeks suddenly seemed ridiculous. How could I be an effective dad while working 80 hours a week? I couldn’t.

So, I quit.

I had absolutely no plan.

For a few months following my exit, I sat on the couch…a lot. I went over and over a string of ideas, business opportunities and next steps and none of them gave me a sense of joy that I knew I needed.

So, I asked myself: What pain would I actually want to solve?

I realized that it wasn’t a clear picture. So, I went and knocked on the doors of 50 area businesses and asked their owners what kept them up at night. Time and time again the responses were the same. Business owners were fighting the good fight every single day trying to keep their small businesses alive in an ever-changing economy. They would put their faith into marketing agencies that promised results and the only results they would actually get were dents in their wallets.

And I wondered: Is there something I can do to put some money back into business’ pockets?

So, I decided to build an app. I created an app that was specifically geared toward getting people in the doors of lesser known local businesses. And it worked. By launch, we had 10,000 active users of the app. The problem: Businesses didn’t want to buy.

After working hard to solve their problem, they still didn’t seem to want their problem solved. I was completely perplexed…

So, I was back to square one of trying to figure out how to solve the issue.

In the midst of some of those conversations, however, business owners had started to ask me for other services in addition to the app: Websites, logos, digital ads, you name it.

With a clear need identified that I could address, I started connecting with software developers, web designers and the like—people who were ready and willing to take a leap into agency world with a process and finance guy as their leader.

Sure, enough, people leapt with me and just a few years later, we had a full service agency that offered videography, photography, web design and development, content and research.

Of course, there is a lot more to that story. There was struggle, triumph, turnover and a lot of sleepless nights. But we’ll uncover the nitty gritty of that later.

One thing that has remained consistent, however, is this feeling that I’ve had. This fear, this inadequacy, this distrust that I’m not actually equipped to do what I’m doing.

“It’s like a man riding a lion. People think, ‘This guy’s brave.’ And he’s thinking, ‘How the hell did I get on a lion, and how do I keep from getting eaten?”

Over the years, and especially recently, I’ve learned that there is a name for that feeling: Imposter syndrome. And I’ve worked to learn how to combat it when it rears its head.

What is imposter syndrome?

Imposter syndrome can be defined as a collection of feelings of inadequacy that persist even if or when you’ve had successes. People who have imposter syndrome often suffer from chronic self doubt and a sense of intellectual fraudulence that can override any proof that they’re actually competent.

As entrepreneurs and leaders, we’re often the first and most likely to experience imposter syndrome because there’s so much at stake in what we do.

In fact, 70% of people experience imposter syndrome at some point in their career.

Do you feel like you may have imposter syndrome? Do you constantly have self doubt and worry that you’re just not good enough?

Type 1: The Perfectionist

Perfectionists tend to set excessively high goals for themselves. If they happen to fail to reach that goal (and they often do because their expectations are too high), they beat themselves up and worry about not measuring up.

If you worry that you may be a perfectionist, ask yourself these questions:

  1. Have you ever been accused of being a micromanager?
  2. Do you have trouble delegating?
  3. Do you often feel disappointed in the results when you have delegated?
  4. When you make a mistake or don’t quite hit the mark, do you tell yourself you’re not cut out for your job or beat yourself up about it for days?
  5. Do you feel like your work has to be 100% perfect, 100% of the time?

When you have so many people relying on you (whether at work, at home or a combination of both), it’s easy to fall into the perfectionist mindset. Afterall, in your mind, a lot more is at stake for more people than just you. What would happen if you let them down?

Here’s the truth: You will let them down. As a leader and an entrepreneur, you have to come to terms with the fact that you are not a perfect human being. You’re going to make mistakes just like your team will make mistakes. Sometimes those mistakes will cause small inconveniences, sometimes they will cause catastrophic problems. What will make you a great leader and business owner is how you face those moments.

Share story of missing payroll…[Insert video of Dustin missing payroll from Instagram]

Some application:

  • Learn to take mistakes in stride
  • View mistakes as a natural part of the process (and trust that process)
  • Push yourself to make a decision before you’re quite ready
  • Start a project you’ve been planning for months

Type 2: The Superwoman/man

You can do everything, right? You can answer all of your emails, get to every meeting 5 minutes early, and jump in on production-related work when your team is under deadline—all while managing the finances, sales and operations for your business.


Do you stay later at the office than the rest of your team, even past the point that you’ve completed your day’s work?

Do you feel stressed when you’re not working and find down time completely wasteful?

Do you feel like you haven’t really earned your title?

Here’s the truth: Leaders can’t know everything. If you are going to be a leader and succeed at doing so, you have to create some space in your workload, your day and your life by removing the clutter.

Some application:

  • Choose one task a week to delegate to a trusted team member
  • Sort your emails to remove any forwards or low-priority CC’s
  • Learn not take constructive criticism seriously, not personally (it’s 100% okay if you’re not able to do everything)

Type 3: The Natural Genius

Natural geniuses tend to judge their successes based on their abilities rather than their efforts. For example, if they have to work hard at something, they must be bad at it. People who naturally did well in school are often sufferers of the Natural Genius imposter syndrome. They have grown to expect natural excellence and any time that idea is challenged, they begin to consider themselves unworthy or not good enough for the task at hand.

To assess whether or not you have the Natural Genius imposter syndrome, ask yourself these questions:

  1. Do you have a track record of getting straight As or gold stars in everything you do?
  2. Were you often told as a child that you were the smart one in your family?
  3. Do you dislike the idea of having a mentor because you feel like you can handle things on your own?
  4. When you have a setback, does your confidence go way down because you’re not performing as well as you think you should?
  5. Do you often avoid challenges because it’s too uncomfortable to try something you’re not good at?

Here’s the truth: You will always have something that you don’t know. You probably don’t know a ton about molecular biology, right? (If you do, let’s talk, because I’d love to learn from you.)

Some applications:

  • Look at yourself as a work in progress and someone who is on a journey to learn
  • Don’t beat yourself up when you don’t reach the impossibly high standards that you set for yourself

Type 4: The Rugged Individualist

Raise your hand if you hate asking for help (✋). People who are rugged individualists with the imposter syndrome believe that asking for help reveals just how unequipped they are to do their jobs.

  1. Do you feel like you need to accomplish things on their own?
  2. Do you often find yourself saying, “I don’t need anyone’s help.”?
  3. When you do ask for help, do you phrase the request in a way that makes it more of a requirement rather than a need for you as a person?

For these rugged individualist imposter types, asking for help is like admitting failure.

Here’s the truth: Just like the Superwoman/man leaders can’t know everything. In order to lead and lead well, there will be times when you ask someone else to step in and pick up some of the work. Are the financials for your business taking you twice as long as they should? Hire an accountant or a finance director to help you be more efficient. Not only will you take a headache off of your plate, but your organization will be more efficient.

Some applications:

  • Assess the areas where you’re holding all the cards just for the sake of ego. What can you let go to a trusted team member or resource?
  • Practice asking for help for a small task. For example, ask a trusted team member to lock up the office for you this week. It’s not a situation where you have to admit defeat, it’s just practice in asking for help.

Type 5: The Expert

The Expert isn’t quite sure why they were hired for their job or why they’re being entrusted as a leader of a team. They often feel like they’ve tricked their employer or team into their position and they are often afraid people will realize how inexperienced or unknowledgeable they are.

  1. Do you shy away from applying to job openings if you don’t meet every single requirement?
  2. Are you constantly seeking out trainings or educational programs because you think you need to improve your skills?
  3. If you’ve been in your position for a while, do you still feel like you don’t know “enough”?

The Expert is the trickiest type of imposter syndrome because, on a small degree, the feelings they have are incredibly healthy ones. It’s important for us to realize that we could always improve and that we won’t always know everything about our field. When it becomes unhealthy and even toxic to our businesses is when those feelings become debilitating in our day-to-day and hinder us from making important decisions.

Some applications:

  • Practice just-in-time learning, like acquiring a new skill exactly when you need it, not beforehand
  • Mentor junior colleagues or volunteer to help collect students to feed that inner expert desire

Move from imposter to executive

The road to leadership, entrepreneurship or success is never straight. In fact, it looks like a toddler scribbled all over the place and even went off the page a few times. You’ll have a lot of dips, a lot of retracing your steps and a lot of lessons learned along the way.

But that’s the process.

There’s a reason there aren’t millions of super successful entrepreneurs out there. This life is hard and it’s a legitimate fight every single day to fight the internal and external challenges that will await you and your business. But the fight is 100% worth it in the long wrong.

Let the process happen and trust that you’re here for a reason.

Whether you succeed or whether you fail, trust that you are doing exactly what you should be doing for the moment that you’re here to do it. That doesn’t make you an imposter, that makes you someone with guts.