Entrepreneurship: Things I Wish I Knew

Ever think about starting your own company? Quitting your job to pursue your dream and living life as a your own boss without anyonetelling you what to do and when? Yeah, we’ve all been there… dreaming of how we’re going to take the world by storm, creating a product or service, starting our business, taking it public and becoming a gazillionnaire, right? Right.

So if you’ve ever daydreamed about starting your own business, either selling a service or launching your own product line, there are a few things that seem great as you set out on your own journey. A few might include…

  • Waking up without an alarm clock: check
  • Not having a boss: check
  • Being free to travel whenever you want: check
  • Being able to go to lunch or happy hour with your friends whenever you felt like it: check
  • Not answering to “the man”: check
  • Bringing your dog to work: check
  • Wearing sweats (or yoga pants) to the office every day: check

Seems pretty cool right? Total freedom. It’s you against the world, and the world is your oyster, right? Right? Well, wait a minute… not so fast. 

Entrepreneurship is like a really crazy, awesome, scary, pee your pants, jump for joy, cry in a corner type of thrill ride at that amusement park you’ve only heard about, but have been really scared to try.  Yeah, I think that sums it up, and this is coming from someone you is still very new to the journey. 

To help paint the picture for you… I do not ride roller coasters. They scare me. Yes, I’ve ridden a few in my life, but I’ve never enjoyed them. You see, I have the fear of falling – of being so out of control, that surely, I’ll slip right out of the seat. (As a side note, I don’t like sky lifts either, but love sitting in the window seat of a plane…). It’s that “tick, tick, tick” you hear as you’re climbing up that diagonal incline that grates me… the anticipation of the steep fall you know it’s coming.  That feeling, that feeling is how you feel when you really start your entrepreneurship journey.

What Keeps Me Up At Night

I think I’m like a lot of other entrepreneurs in that there is sometimes (not all the time) a thought in the back of my head that asks, “What the heck did I just do?” For me, I left a great seasoned, corporate career, finished my MBA, have a fresh new pile of debt from student loans, and decided to pursue my dream, which leads me to the OMG moment of “What the heck did I just do?” Did I really spend all of that money to pursue a graduate degree, to leave a corporate gig with “security” and benefits?? People think I’m crazy, my parents think I’m crazy, the job offers I turned down think I’m crazy… and I too think a little crazy might be showing through…

In addition to the “What the heck did I just do?” question, the “What If’s” really also take their toll. 

“What IF I fail?” “What IF I can’t get back into the job market?” “What IF I run out of money?” “What IF no one pays for my products or services” “What IF I can’t reach new customers this month?” There are millions of “What IF” questions you can ask yourself, and if you aren’t careful, these questions can keep you from reaching one of your greatest achievements. 

The “What IF’ questions are very real, and all of those questions are the ones that keep me at night. 

What Happens When You Change Your “What IFs?”

But instead of having these questions consume me, I use them as my motivator or change the context of the question. The two “What IF” questions that caused me to change my outlook were:

“What IF I never pursue my dream; how would I feel?” – Pretty crappy. After 20 years in corporate America, and 2 years of business school, I think I deserve to take a chance on myself and see what I can accomplish in starting my own business.


“What IF my business is successful?” Oh crap, you mean I could really be successful at this? This adds an entirely new layer of the idea of success – now I am truly the master of my own destiny, and if I’m successful, that means I have to continue to work harder, better, more efficiently in order to maintain that success. How do I scale? What’s my long-term strategy with this business? 

By changing the context of my “What IFs”, I was able to focus on the positive and begin to strategize on how to move forward in my entrepreneurship journey. The slight change of focus made a world of difference and help me put my goals into perspective.

It Takes A Village

Don’t get me wrong… entrepreneurship is one of the harder things I’ve set out to do. And one of the most important lessons I’ve learned throughout this journey is that you cannot go at it alone. You need your cheerleaders, those loved ones, family members, or friends who do not think that you’re crazy, but will support your dream. The people who will listen and encourage you when you want to give up, the ones who will provide construstive feedback, and the ones to tell you when you may need to change course.  

And other things I wish I knew before starting my journey…

  1. You will want to give up. Often. But don’t. While every venture may not be successful, make sure you learn the lessons in your journey that may make your next venture a success!
  2. Don’t forget to be social. If you’re starting a company by yourself, and spend hours on end trying to pull things together and make it work.. don’t forget to still have lunch, coffee, happy hours, etc. with friends. Yes, the work may all fall or your shoulders, or you would rather save money and not go out, but being social and having fun with friends will rejuvenate you in ways you may not even realize. 
  3. Save, save, SAVE! If it takes months to get your business off the ground, find customers, or earn a profit, you want to make sure you have your “entrepreneurship fund” in place before you quit a job and venture out into your own business. Those small items like $5 daily coffees, or eating out multiple times a week will start to add up. There will be unexpected business expenses that you may need to cover in your first few months of operations. 
  4. You’re the Boss of You! This is what you’ve always wanted right? Well as the boss, everything starts and stops with you. Make sure you’re on top of your schedule, invoices, contracts, clients, marketing, social media, etc. If you’re not good at all of these things, make sure you have the people or the systems in place to help you stay on track!
  5. Enjoy the Ride! Yes, it can be a scary, crazy roller coaster ride. But you’ll survive, and at the end of it, you’ll be so happy you met the challenge and be ready to do it all over again!




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