7 Dirty Secrets of Entrepreneurship

7DirtySecretsofEntrepreneurshipI love what I do and I’m the consummate optimist. Even when things are rough, I can find the silver lining… But there are a few things I wish I would have been more prepared for when I started my business. I am listing them here, along with a counterpoint – the ‘silver lining’.

Business owners talk about these things among themselves but rarely share them with others. After almost 4 years of ‘doing my own thing’ I wanted to lift the veil on some of the more challenging aspects of business ownership.


7 Dirty Secrets of Entrepreneurship:


    1. Loneliness:
      You work LOTS of hours (especially at first). You barely have time for family and shy away from hobbies. Your existing friends may not understand the pressures you will face, and you won’t be able to relate as well with people that have ‘normal jobs’. Because of these issues, it can feel really lonely – especially for people (like me) that were used to developing relationships at the office or having a ‘work family’. Even if you add employees, you are now the ‘boss’ and it’s not the same as the camaraderie as you had with your old friends ‘at the office’.
      Silver Lining: Other entrepreneurs are lonely too, and through your work, networking, professional organizations or mastermind groups, you will become great friends with other business owners.


  • Roller Coaster:
    You’ll feel afraid 50% of the time, and invincible the other 50%. This will make you a borderline lunatic.
    Silver Lining: If embraced – these emotions keep each other in check, so your ego never blows up too big, because the fear of failing is right around the corner. Plus – Roller Coasters are fun!



  • Too Many Hats:
    You’ll feel like a juggling octopus. A business requires; client development, client retention, project management, marketing, fulfillment, billing, technology use/fixing, networking, collections, managing expectations, employee/partner management etc. – and sometimes all in the same day.
    Silver Lining: You become very aware of what you are good at. I know people that spend their whole lives working at jobs they hate. I never wanted to do that… I also never knew exactly WHAT I was great at until starting this business.



  • Pain Management:
    Does you FACE HURT? IT’S KILLING ME. Your teeth will hurt. There isn’t a good comprehensive health plan for your teeth if you work for yourself… So you may go without good dental care for awhile. If you have a spouse, partner or children, they may take first priority in the ‘teeth area’. *You can replace ‘teeth’ with back, or eyes, or joints – the ‘normal stuff’ you would stay on top of with a corporate health plan.
    Silver Lining: If your business is successful, the long term ‘benefits’ will have more to do with time and opportunities you can provide for your family. That’s one of my big motivators.



  • Office Overdose:
    Working at home is R E A L L Y difficult. Nobody tells you this. I dreamed of a home office when I was driving an hour one way to work… After about 14 months of working at home, I couldn’t wait to get into some kind of office again. At home, it’s easy to start work when you wake up and stop working when you go to sleep. It’s also easy for someone to ask you to ‘switch the laundry’. There’s nothing wrong with taking a break to switch the laundry, but if you are 2 hours into a digital marketing plan, the question “can you switch the laundry” might as well be the ‘Men in Black’ brain scrambling device. It’s impossible to start at that same level of creative product creation after switching the laundry.
    Silver Lining: You can do crazy cool things like go to your kids school programs, take a nap, go for a walk, play a video game, watch the NCAA Basketball Tournament, go hang out with your entrepreneurial buddies, have coffee with your mom, go to a movie with your in-laws, go see your brother 5 hours away, and have lunch with your family. All of which I have done in the middle of a ‘work day’. It’s easy to make up the time early in the morning or late at night in a home office.



  • Cash Clogs:
    You will always want to invest in the business, yourself, your staff and your ideas. You may get frustrated that everyone gets paid before you do… It’s YOUR business after all! I’ve heard the term ‘cash is king’ but honestly, in business, cash FLOW is king. Get your head around going without personal stuff for awhile so you can have a reserve. Also, if you aren’t great at managing money, (I’m not) make sure you have a KILLER accountant. Building up reserves is hard and takes longer than you want.
    Silver Lining: In my experience with a job, there was always a set amount of money that you received every couple weeks. When you are self employed or own a business, there may be times were you have access to larger sums of money, allowing you to leverage your buying ability for investments and let’s be honest a refrigerator or vehicle. It’s fun to pay cash for large purchases if you can manage. Usually you can get a better deal with cash, and you will come to loathe payments.



  • Work Wheel
    Your work is never really “done”. Sometimes having fun makes you feel guilty. A night out with your family, a hobby, a vacation, a 3 day weekend, a day of golf, watching tv, a long meal, seeing your uncle – all can lead to feelings of guilt. Your business needs more than you can ever give it.
    Silver Lining: Having this level of commitment, leads to a passion for what you are doing that simply can’t be found working for someone else.


What do you think? Do you agree with this list? Any one of these ‘secrets’ resonate with you? What would you add?

  • Tiffany

    Absolutely agree! A few years ago I found myself taking the leap into running my own business and I experienced every single item on your list. It was quite shocking and some aspects I didn’t handle very well. I ended up closing the business and hopped back into corporate world. But ever since then I’ve daydreamed about going back out on my own. I was bitten by the entrepreneur bug and I’m afraid there is no looking back. In the process of starting a new business.
    I think one of my major problems was lack of focus. Since I had to wear so many hats I found I was running in circles and wasn’t getting enough done. And then my head wouldn’t turn off at night because of all the things I needed to do or worried about – then insomnia creeped in — and that was the worst for me.

  • angelaengland

    These points are SO true. But as to #7 – I make the fun times rewards for the achievements. Launch the course – take my family out to a family fun night. Sign my 50th student – vacation time baby! Finish my book, weekend away. Build the fun into the rewards and you can play guilt free because you’ve finished the work. A work, at least.