Honestly, I’m not sure what the word on the street is about being an entrepreneur — Probably that it’s a lot of hard work; that it’s amazing to be your own boss; that if you’re dedicated you will succeed. It’s also no secret that there are a lot of really great business ideas out there and a lot of good companies that fail (I believe the odds are that only 2 out of 10 startup companies succeed — betting people would say that’s a horrible gamble). Let’s gather all possible pitfalls of being an entrepreneur.

What you really need to know

That may be the buzz, but over the past few years, I’ve launched my own businesses and supported others during their own startup processes. There are a few things I’ve learned that I wish someone would have told me upfront.

So, here is my version of what you need to know:

1) (Almost) Everything takes longer than you (want) think it will take.

When you are start your own business, you want it to be successful as soon as possible! There is anavlso this amazing thing called revenue that determines your success. Revenue is different from total profit and it is important for you to understand the difference. If you have an investor, or friends/family are loaning you money, or even if you are self-funding your venture, revenue is a big deal, but it doesn’t just come in overnight.

However, the point is: It takes time to build anything. There are many folksy sayings about this…cough, Rome, cough. There are times when an original business idea isn’t a viable option in the marketplace, so even the timing of the idea itself has to be considered. 

Thus, patience and remaining optimistic, are key elements to remember when you start your own business venture. Each step along the way is important, so when you put one foot in front of the other always have the end goal in mind. Optimistically plan for project #1 to take 3 months, but don’t be upset or surprised when it takes 5 months instead. Keep pushing. 

2) Everyone has an opinion about what you should or shouldn’t do.

I’ve written more about this here. I realized early on that there’s an entire industry of consultants that help nascent companies with various subjects –marketing, vision strategy, management, finances, real estate, HR, social media, etc. You may or may not be connected to a network like this, but even your family and friends will have opinions. Don’t let those opinions and comments distract you – let them inform you.

Once I realized that no one knew my business better than I did, I had a more confident attitude and a direct approach when discussing my ideas with others. I learned to listen thoughtfully, to ask questions, and then to take the bits they said that were relevant to my vision and use those ideas to improve upon the foundation of my business.

3) The risk is on your shoulders so with that comes stress, pain, inner reflection and problem-solving.

The major element of entrepreneurship is risk, which is also the reason a lot of people don’t do it. Risk that the business doesn’t work. Risk that you lose money or you lose your investors’ money. Risk that the idea is great but the product you build isn’t functional. Risk a competitor gets to the market before you do (or opens a shop next door). If you’re risk adverse, then entrepreneurship might not be for you. However, in line with our Nav.it philosophy, how you manage the fear of risk is the key to alleviating a lot of stress, pain and stagnation when starting a business. Managing your fear of risk taking so that the majority of the time you are confident, informed, and proactive, will greatly assist you in this process. 

For me, managing risk has always been a 3-step process: acknowledging it, learning as much as I can about it, and then assessing what I should do about it. (Should I completely ignore it, do something to mitigate it, or change course because of it). Risk is a part of our normal daily lives and entrepreneurship heightens its presence. Remember, we all take calculated risks every day (crossing the street, choosing where to live, driving in inclement weather or heavy traffic), so you already have the basic skills to manage it.

4) You need a game face

For me, getting my game face on has helped me Nav.it. That means I drag my Warrior self out of the pit of my stomach and imagine that I am wearing armor. In my most shaky times, I call it “pulling out my Joan of Arc” and stand ready to fight for my cause. I had to learn to do this, I don’t naturally love conflict. However, to make a business happen the Warrior in your needs to be ready to stand her(his) ground.

An entrepreneur friend of mine calls it her Soccer Warrior, because she imagines how she feels when she attacks the goal and focuses on scoring (btw, since she has started doing this visualization, she has scored way more goals in her soccer league, so maybe this has extenuating benefits!).


5) Sometimes you hit a roadblock that is a real roadblock (i.e. be flexible)

Flexibility when starting a business is vital. Nothing goes exactly as planned, you won’t know every single regulation or legality that affects your work. One step at a time and if you must adapt, adapt. It’s the key to success because an excellent business plan is exactly that: It’s a plan not an action. Once you start acting on that plan be prepared to modify, tweak, improve (and sometimes change course entirely) to get it right.

6) You can wear whatever you want to work.

This one speaks for itself, but the beauty of being the boss is you usually get to create your company’s organizational culture. So, if you want to have casual Friday every day, more power to you. If you can and want to work from home; work from home. It’s true, that the risk is on your shoulders, so you want to create a work culture that fits both your business and your personal style, but the level of freedom entrepreneurship brings to your professional life is pretty fab.

7) You don’t know everything that you need to know, so surround yourself with good people. 

Again, you don’t need experts telling you what to do with every aspect of your business. However, experts can be very useful in developing specific aspects of your business, and surrounding yourself with a good team is seriously helpful.

When interviewing and hiring consultants, there is no urgency, take your time to find the type of consultant that listens and adapts their services to meet the needs of your company. As your company grows and your needs change, you may need to let go of consultants that are not helping you expand your business. Don’t be afraid to make changes along the way – sometimes you outgrow things or ideas that were initially working for the company.


There is nothing easy about starting your own business, but a helleva lot of things are incredibly fun, inspiring and fulfilling. Doing work that you love, collaborating with people you like and who are good at what they do, setting your own rules, and watching the labors of your efforts take root, are the amazing rewards.  To me, they far outweigh the blood, sweat and tears that go into the initial startup. Is it really worth it? Only you can know that. Pitfalls of being an entrepreneur are all manageable. But if you do go down the entrepreneurial road, don’t half-ass it. Be ready to put on your Warrior self and Nav.it like the rock star you are!