I woke up at 5 a.m. this morning completely unable to sleep. Why? Because in 24 hours I was supposed to be on a plane en route to attend my kid sister’s wedding… and I knew there was no way I’d be able to get on that plane.

Edited to add: Please see the final “note” BEFORE commenting. :)

I dreading sending the email to explain that I wasn’t coming – and why. And I knew that no matter how I explained it, as someone who wasn’t an entrepreneur, my kid sister likely wouldn’t understand.

Being an entrepreneur has been one of the most rewarding experiences of my life. But it’s not all kittens and rainbows. There are times that you have to make tough decisions that seem like “choices” to non-entrepreneurs when they really aren’t.

I’ve been self employed via various different ventures for over a decade. I admit to being somewhat of a “serial” entrepreneur. I start a venture, dedicate myself to it for a few years and then – if all goes well – I get to reap the rewards (which to me is being able to do what I want, when I want, how I want). But there always seems to be another opportunity that comes up and (this is where the “serial” part comes in) I always find a reason to take it.

The first few years of starting a new venture are undoubtedly the hardest (in my experience). When I decided to come out of what my friends liked to call “semi-retirement” and start PushFire this year, I knew exactly what I was getting into. But, I definitely forget the LEVEL of sacrifice involved in building a company from the ground up every time I start a new venture. I tend to compare serial entrepreneurship with having children. You know it was hard, but you forget HOW hard it was until you decide to do it again.

To the “regularly employed” entrepreneurship means freedom and doing whatever you want. But seasoned entrepreneurs know better. We know that those benefits only come after you put in several years of hard time – and even then, it’s not always guaranteed. And those benefits come at a cost.

“Entrepreneurship is living a few years of your life like most people won’t, so that you can spend the rest of your life like most people can’t.” ~ unknown

The costs of being an entrepreneur

Serial entrepreneurs will likely nod at many of the below. People thinking about becoming entrepreneurs need to realize that they’re going to experience the below. And I hope that people who are not entrepreneurs will get some insight into those that ARE via the below.


What non entrepreneurs think:


The reality:

Beginning a new entrepreneurial venture means giving up your time now in order to have more time later. There is no five o’clock stop time in the beginning of a new venture. When you’re not in the office, you’re thinking of what you need to do when you’re in the office. When you’re at your kid’s football practice, you’re on your smartphone answering emails (but hey, at least you can attend the practice). Instead of watching Law and Order on the couch at night, you’re on your laptop creating proposals or budget projections. Going on vacation (or attending your kid sister’s wedding) becomes a nearly impossible task because leaving the office for four days for anything not business related is simply not an option.

You made a commitment to yourself, your partner(s) (if applicable) and your team to ensure what you need to get done to make the business a success gets DONE. And until you’ve reached the peak, time is your most important and needed input into a new venture.


What non entrepreneurs think:


The reality:

Unless you have gotten funding (or a loan), then the money to propel your new venture is coming from you. I’ve never taken the funding route and instead have invested my own money and then reinvested profits from every venture I’ve ever started to build it to the level I want it to be. There’s no “fat paycheck” from a new venture. Know that if your short on cash at the start, you’re going to be eating hot dogs and Kraft Dinner for a long while before you start being able to pull any decent money from your new venture. And no that the return on that money is never, ever, guaranteed.


What non entrepreneurs think:


The reality:

On top of the money and time involved, entrepreneurs deal with a hell of a lot of stress. Being responsible for the success or failure of a business is stressful. You’ll worry with every new hire whether or not you’re choosing the right person. You’ll worry if every item you choose to spend money on is a “smart” expense for the business. You’ll deal with a lot of self-doubt while needing to appear as if you know every move is the “right” move. Knowing that your success or failure effects your bank account (and the bank accounts of your investors if you have them), the livelihood of your employees, the families of those employees and the livelihood of the customers you are providing services or products for… it’s not for the faint at heart.


What non entrepreneurs think:


The reality:

You’re going to be busy as hell. And as a result of the amount of time you’re going to have to put into your new venture, you’re unavoidably going to alienate people. You’ll forget to return phone calls because you lost track of time while proofing your new HR manual. You’ll miss birthday parties because a deliverable is due and you’re going to be spending your night ensuring it gets done. And because non entrepreneurs don’t understand your reality, they see it as a conscious choice and not as the absolute unavoidable you know it to be. Some friends and family will go from understanding, to annoyed, to insulted to not speaking to you.

In my early years of hard core entrepreneurship, I was single (or at times dating other entrepreneurs who “got” it). In my current years, I’m married to my business partner. But, if either of those situations does not apply to you, then you can expect any romantic relationships to get stressed over – and in some cases, possibly not survive – your entrepreneurial venture. If you have children, they’ll likely feel second to the business at times and you’ll have to work very hard to ensure it doesn’t happen to a significant level.

The benefits of being an entrepreneur

Now, at this point you might be thinking “What the hell? Why would ANYONE do this?” and the answer is, the above is exactly why not JUST ANYONE does. But for those willing to put in the costs, the benefits make it all worth it. Because if you’re successful, then you’ll reap the costs you put in ten-fold.

You’ll have MORE time, MORE money, LESS stress and all of those will make you a happier person who then can spend more of their inner resources on their relationships with their family and friends. I know this because I’ve made it to the peak with other ventures – and I damn sure will make it to the peak again.

And if my sister is still speaking to me at that point? I plan to make it up to her.


I did not post this to ask for family relationship advice. Unless you are Dr. Phil and would like to spend a day with me learning my family dynamics, then anything you post about what *I* should do is irrelevant. I however welcome hearing what YOU hold dear and what YOU have done in tough situations and what YOU have been willing to sacrifice or not.

The POINT of this post was to highlight tough decisions and sacrifices entrepreneurs have to make sometimes and how they are sometimes perceived by people who are not entrepreneurs. However, it ended up showcasing that the reality is that no one should judge ANYTHING they don’t understand – not just entrepreneurship.

PS… if you ARE Dr. Phil and would like to have lunch, hit me up and we’ll schedule something. ;-)

Is Pinterest part of your marketing plan?

Check out my recent case study that shows how I generated 234,000+ pins (and counting) to a site with only 45 posts. I give you all the details (with specifics) here.