So You Want To Be A Corporate Drop Out?

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I always knew I wanted to own my company. From a young age I would try to find any way to monetize my abilities, make some extra cash, and use it to fund the next business venture my little 10 year old mind would conjure.


When I owned a lemonade stand in the summer I chose to use a neighbors yard instead of my own. The yard I chose was at the entrance of the neighborhood AND the entrance to my cul de sac - which resulted in the best location to be seen by neighbors and random passerby. If that wasn’t enough to catch possible clients eyes, I would make my little brother do headstands to promote our “Headstands for lemonade stands!” campaign sign I had made to garner attention.


When I started house sitting for neighbors, I would make homemade dog treats to include as an add-on package to my $5 a day home care charge, which eventually became a homemade dog treat business that was able to carry me through 3rd grade with a couple hundred bucks in my savings account.  


During the summers, I owned a concession stand at our neighborhood pool, took out a $50 loan from my parents to buy a sno cone machine and made sure I was scheduled on Fridays. Reason being, I knew that day camps would come to our pool on Fridays and kids would pay up to $2 a sno cone - an item that no other concession stand owner had.


Basically - my neighborhood helped me become a mini CEO of various companies.


Fast forward 8 years and I found myself at one of the top business schools in the nation pursuing a degree in Management. While there, I realized that all of the practices my elementary self did to make money were actually legit business terms.


The small microloans I took out from my “Bank of Parents” helped me understand basic accounting rules (i.e. you must pay back the loan, cost of goods and labor before you can consider anything profitable). My lemonade stands marketing campaign was not only clever, but proved it’s all about location, location, location. My snow cone business showed that having a differentiated product would increase your business and set you apart from competitors.


Fast forward another 3 years (because helllloooo early graduation and thank you AP credits) and I found myself working at a top tech firm in Austin.


While the business acumen and soft skills of grit, hardwork and perseverance were invaluable while I was living the corporate life, I knew that I wasn’t using the skills I was gifted with to my full potential.


Enter the side-hustle. To all of your corporate ladies (and men!) who are clocking in and out from 9-5, feeling stuck in your current role and looking out the window longing for the day when you finally are able to work on your company full time and be declared a successful “Corporate Drop Out” - I hear you. I know you because I was you.


While I loved my coworkers, I knew that I wasn’t created to make cold calls and sell tech applications.  


I lived for the weekends when I would get to spend 14 to 16 hour days with bridal couples, making their wedding day flawless. I craved being the person behind the scenes, helping direct an evening that would be remembered for forever. And as weird as it sounded, I longed for the ache that Sundays brought after working nonstop on my feet.


That passion - that energy and that desire to give my all to my company drove the decision to take a leap of faith and dub myself a corporate drop out.


Now in business school, I had learned about tech startups, companies that were utilizing smart technology to make 3D printers, how to secure angel investors and file for patents, but no one ever really talked about how to start your own wedding planning business…


So how the heck was I supposed to become a successful corporate drop out as a Wedding Planner?


Well - no matter what industry you’re wanting to enter I think that there are five very simple, very important aspects of becoming a corporate drop out that will set you up for success no matter what industry, product, or service you’re wanting to enter into.





Rash decision making is never a good idea. While you may be fed up with your current job and dreaming about the dramatic exit you will take, claiming you’ll be the next Steve Jobs, no one at your company will appreciate the theatrics. Look at your company’s fiscal year - would it be possible for you to continue working until the end of the fiscal? Additionally, is it possible to give more than a two weeks notice to your manager? Finding qualified, professional employees is difficult, and with you leaving, you’re putting your manager in a spot to find and fill a position that they may not have foreseen needing to fill. Lastly, are there any bonuses coming out? If your company gives out holiday bonuses, it may be worth it to continue working for another 2 months to receive that additional income - you are after all, entering into a world of unpredictable income...





Which leads me to my next point - having a healthy savings account will allow you to continue living within your same means and not freak out about how you’re going to pay next month’s rent. Look at your monthly expenses - including credit card usage, mortgage/rent, utilities, entertainment, car payment, gas, tithing, etc. add about $250 a month for unforeseen expenses, and multiply that by 6. Having half of a year’s worth of savings will allow you to not worry about your income, focus on your business’s growth, and not go into debt while trying to start up your company.





While living off of savings is a way to ensure your financial stability during a career journey that is full of unexpected income mountains and valleys, as an entrepreneur, we want to start making money for the company as quickly as possible. To do this we need to set benchmarks and goals to keep us trucking along. The best types of goals are “SMART” - an acronym for:

S- Specific

Ex. I want to sign new customers to my business.

M- Measurable

Ex. I want to sign 50 new customers to my business.

A- Attainable

Ex. I want to sign 5 new customers to my business.

R- Relevant

Ex. I want to sign 5 new day-of coordination customers to my business.

T- Time Sensitive

Ex. I want to sign 5 new day-of coordination customers to my business within the next 30 days.





Not having accountability while running a business is like trying to lose 50 pounds and never going to the gym - absolutely pointless. Finding like-minded people who are invested in your company and your vision gives you a community who will gently and firmly remind you of your SMART goals and keep you on track to meet them.





No one will care more about your business than you. That being said, you need to be willing to go after what you want, be bold and be confident in the product and/or service you are providing. Get aggressive with your marketing campaign, keep your brand name at the forefront of people’s social media accounts. Every time I saw a couple get engaged on facebook, I would message them to set up times and dates to talk about being their wedding coordinator. When I was a sales rep, we called this the “hunter vs gatherer” mentality. You could be a farmer and sit and wait for your crop to grow and harvest or you could be a hunter and get out of your cave man home and get after the delicious piece of mammoth you’ve been craving to hunt.


In the beginning stages of your business, you need to have the hunter mentality. No one else is going to hunt for clients like you will, because no one else’s paycheck is relying on it like yours is. Be aggressive. And don’t let the word “aggressive” make you feel icky. There is an appropriate way to be an aggressive and successful and well-liked business owner, but let’s save that for another blog post.




In the meantime, if you’re currently waiting and dreaming for the day when you can become an official corporate drop-out, start small with these five steps to make sure that your business is in the best place it can be when you are finally able to kiss corporate good-bye and say hello to self-employment.


Xoxo Kara