• Callahan Carr

How I Found My WHY…An Open Letter to Women Starting Their Own Business

Updated: Apr 9

Written By: Callahan Carr

I landed an internship at my dream company the last semester of my senior year of college. I worked hard to learn the ins and outs of what they needed me to do. I wrote for 9 episodes of a weekly broadcast and clocked hundreds of production hours both in the studio and on location. I had learned so much in such a short time and I thought I would have been ready to move into my new office, put my name on the wall, and start making beautiful work for television. But instead, I finished the semester sobbing and broken.

That dream job I had envisioned since I was a gangly 12-year-old watching that channel every Saturday morning, just slipped through my fingers. I thought once I was behind the velvet ropes I had arrived, but in reality I had less choice and less voice. Had I just wasted all these years and education chasing a dream that I no longer believe in?

I would go on to hold multiple jobs where I had the illusion of creativity and freedom. I was chasing safety and security at the expense of my own freedom and voice. I was making decisions based on fear and controlled by pain. The pain I was feeling was rooted in knowing I didn’t have autonomy over what I was producing, what my career trajectory was, or how all of these things impacted the rest of my life.

Nearly a decade removed from that pivotal internship and I now work with right-fit clients (that I choose). I have the time and money to create at-will. I sell my ideas and help other female entrepreneurs to hone their expertise and reach their own right-fit clients through impactful video. I no longer exchange my time for money while putting my dreams on the shelf. I travel when I want to travel and I get to work from anywhere. The caveat to this is not that it’s without hard work or hard lessons along the way. The funny thing is- when you are our own boss, you also tend to be your toughest critic.

I calculated I spent four years trying give myself permission to exit a work life I grew to resent. It was ridiculously hard, and it was so emotionally draining, to the point it began to affect my self-esteem. So, a couple of years ago I decided to break down, into its individual parts, how I went from a dead-end work-life to being a full-time entrepreneur and business owner.

Those first years of wondering if I would ever pull the trigger and build the life I’d always seen for myself were so painful and sometimes so incredibly lonely that I decided a year ago I wanted to help other female entrepreneurs to shorten the distance and lessen the pain between anonymity and work/life success. In order to do that I had to talk to a ton of women struggling to find their own path. I had to find out what pained them, where they were stuck, what angered them and even what humiliated them. Then I had to find out where they wanted to go, what their dream was and what their ultimate day looked like as the owner of their own business.

I had to do this, so I could get a clear understanding of the best way to help them. It was then that I realized that most women who want to start their own businesses and take their lives into their own hands are all cut from the same cloth. I realized they were me. They struggled with the same things and fought the same battles, and all needed the same thing. They wanted to have control over their career path. One that didn’t rely on someone tapping them on the shoulder and telling them they were talented, and they wanted predictability around money and time.

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Below is a list of the top PAINS and DREAMS I hear from frustrated female entrepreneurs…


  • I’m overwhelmed

  • I’m not proud of the work I’m doing at my job

  • I don’t feel seen

  • I feel held back

  • I’m living a life I didn’t choose

  • I have no free time to work on my starting my dream business

  • The only places I go are work and home

  • I’m trapped in never-ending gig work/menial tasks

  • I get no recognition for the great work I do at my 9 to 5

  • I don’t have a giant contact list full of people who want to help me

  • My boss is a is a jerk

  • I don’t know how to get started building my own business

  • Because I’m unfulfilled, I find I can’t enjoy the free time I do have


  • I choose the clients I work with

  • My time is my own

  • I’m proud of the work I’m doing

  • I’m surrounded by a great, creative and inspiring team

  • I have the financial resources to build my business the right way

  • People call me instead of me hustling to find work

  • I can travel or take a vacation when I want to

  • I know people who can buy/pay for my amazing work

  • I have an engaged audience and client base that recommends my business to others

  • I love getting up and going to work

In the end, I meet so many female entrepreneurs that didn’t think this was possible. I meet so many women that don’t believe their work can be expensive or have real market value. They know their business has value, but don’t trust it can make them wealthy. By wealthy, I mean their day-to-day life needs are met, they have choice, and they aren’t working under financial duress. Now don’t get me wrong, even if one manages to achieve these things, it’s still hard, it’s still a fight, it’s just not suffering… and working in that kind of day-to-day tension can be mind-numbing at best and get you to quit at its worst.

So, if you feel this way or feel stuck on how to take the first important steps toward creating the business you’ve always seen yourself having, let’s set up a free strategy call and talk!

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If you’re needing a kick in the pants to get on camera more and create livestream videos for your business — — join my 5 Day LiveStream Challenge. It runs from 9/30–10/4 and just for signing up you get a HUGE bonus ebook that is the ‘Ultimate Guide: 26 Prompts for Creating Your Own High-Impact Video Campaigns’ that you can start with today!

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