Entrepreneur, Getting Started

Boss Talk: Did You Have Any Fears When You First Started Your Business?

Episode 334: Show Notes

We’re pumped to do another Boss Talk episode today! Our question for today is, “Did you have any fears when you first started your business?” Before we jump into this though, it’s worth mentioning that Emylee has a habit of conveniently forgetting all the negative memories of an experience, looking back at them with rose-colored spectacles! Nonetheless, we’re talking about fears and what it was that drove our decisions in those early days of starting our own businesses.

We’re pumped to do another Boss Talk episode today! Our question for today is, “Did you have any fears when you first started your business?” We’re talking about fears and what it was that drove our decisions in those early days of starting our own businesses.   |  The Strategy Hour  |  Boss Project

Many factors played a role in those decisions, including long-distance relationships and being desperate to move closer to our families. In this episode we share some of our fresh-out-of-college experiences trying to navigate new phases in life and trying to figure out what our next steps would be. We also chat about confidence and what motivated us to start our own businesses and the many considerations involved, so join us to find out more about our early days as startup entrepreneurs!

Emylee’s After-College Journey In A Family Of Business Starters  

Emylee started her business out of a place where she had no other choice, so she was kind of pressured into it! After graduating college, she found herself at a crossroads of wondering what the next step was. Growing up in a family who started their own businesses in some shape or form, Emylee knew that she could do it, but didn’t have the money to. She also realized that she would have to get an income to start paying off all her student loans. She admits to going into it a bit naively, expecting it to be a certain way, but it turned out very differently. But now, eight years after starting her first business, she is grateful for how it has all worked out. Sometimes being confident and really believing that you can do it is what helps you set the process in motion.

Desperation As The Driving Force Behind Abagail’s First Business   

Abagail on the other hand started a number of side businesses before committing to one specific thing. All these side hustles allowed her to ‘play’ business and prepared her for the real deal once it came around. When she got more serious about business, she didn’t have a lot of those initial anxieties that first-time entrepreneurs often have. But what she did have was a whole lot of desperation. Being the breadwinner when she first got married, she had to provide for both of them while her husband was looking for a job after relocating to where she was. They eventually bought a house, but after he had found a job, she was laid off. So she decided to go all in to start her own business, knowing that if she failed, she’d have to go back to a corporate job and a 45-minute commute where she’d be frustrated most of the time. The fear of that reality gave her all the motivation she needed!

Family Matters: Wanting To Be Close To Our People  

Early on in our careers, we both had a real desire to be close to our families. Raised in the Midwest and being new out of college, we were still developing as adults, finding our way and felt like being close to the people we love was really important. That is also a challenging time of change for a lot of people, because whether you continue on to grad school or start working, your familiar environment inevitably changes and you have to keep adapting. For the two of us who are very family oriented, we needed that sense of security of a solid support system. It’s important to know what kind of person you are in this process and accept yourself for who you are. If, like us, you are close to your family, it might not make sense to move across state to a big city job. So we knew we needed to figure something out and do the kind of job that would allow us to remain close to our loved ones.


We wish someone had told us, ‘Quit sweating the small stuff.’
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What We Wish Someone Had Told Us About Business   

Even though we wouldn’t necessarily change any part of our journey, there are some things we wish we had known before. Abagail wishes that someone told her not to sweat the small stuff, not to get hung up on minor things that go wrong in business. Because she started her business from scratch after being laid off, and had basically taken a massive risk, the tiniest things would make her feel like it could derail everything she’d built up to that point, so she’d get freaked out by what in retrospect were tiny obstacles. There is a certain thing that Emylee would like to have done differently, though. Looking up to other people and following their lead really helped her in the beginning to formulate exactly what she wanted to do. She had a mentor whose business model she effectively adapted for herself. But there comes a point in business where you need to keep your head down and ask yourself what you really want and how you would like to get there. Using someone else’s model is fine for getting yourself started, but then you need to re-evaluate and customize it to meet your own needs.

Our Personal Run-in With the Dunning-Kruger Effect  

If you’ve never heard of the Dunning-Kruger effect, we’re here today to tell you how real it is, because both of us experienced it! It’s a cognitive bias where you have self-awareness and recognition in the beginning but where you then take a confidence dive after you are hit with the reality that you don’t know much at all. So just when you are getting started and have no experience, your confidence may sky rocket immediately and you think you have it all figured out. But then what ironically happens is, as you gain experience and see things in greater perspective, your confidence dips until you hit an all-time low. Then as you grow and learn and get closer to becoming an expert, your confidence slowly builds again. The time frame for this happening is much longer than what we’d like it to be, however. It can be years and it can kill a business if you’re not careful. So going through the normal ups and downs is, well, normal! You’ve just got to stick it out.


  • Emylee’s after-college journey in a family of business starters. [0:03:12.1]

  • Desperation as the driving force behind Abagail’s first business. [0:05:10.1]  

  • Family matters: wanting to be close to our people. [0:19:47.1]  

  • Our personal run-in with the Dunning-Kruger effect. [0:28:56.1]




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We help overwhelmed and creative entrepreneurs break down their Oprah-sized dreams to create a functioning command center to tame the chaos of their business. Basically, we think you’re totally bomb diggity, we’re about to uplevel the shiz out of your business.


  • Fear.

  • Entrepreneurship.

  • Family.

  • Long-distance relationships.

  • Dunning-Kruger effect.




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