The 4 Delusions of Entrepreneurs

Ask an aspiring entrepreneur why they’d kill to make the jump and, without fail, four of the top 5 reasons will be:

  • Freedom
  • Control
  • Money
  • Passion

They dream of working their own hours, not having to report to “the Man,” skipping though fields of money, loving what they do every moment of every day and changing the world. All great aspirations.

Question is –

How much is real, and how much is outright fantasy?

Let’s take a deeper look at the 4 big entrepreneurial motivations, bust a few myths and open a few eyes:

1. Freedom.

First let’s break it down. What do people mean when they say freedom? Sometimes they mean geographic freedom or what people have come to know as the ability to be location independent. Sometimes they mean financial freedom. Sometimes it’s the freedom to do what they love. And, other times it’s freedom from a fixed schedule. Or, not having to follow the orders of a boss. Either way, there’s a lot of myth here.

Geographic freedom – If the type of business you are drawn to creating is largely online and the places you’d like to travel to and work from are wi-fi’d up, there’s a good chance the dream of location independence can be real. This was a big theme in Tim Ferriss’ 4 Hour Workweek. And, Lea Woodward, takes it a step deeper in her blog, But, you’ve gotta be realistic. Many other types of businesses that seem to have potential for location independence, upon deeper analysis, don’t. Or, at the very least, the logistical challenges and stress created by them would make it not worth the effort.

Also, if you’re drawn to brick and mortar, especially face-to-face service driven businesses (which, oddly enough, I am), location independence becomes a bit of a myth. You still need to find and locate yourself where the people who are desperate for your solutions work, play and live. Put another way, if you want to surf the big waves, you’ve to go to the ocean. It won’t come to you.

Financial freedom – Okay, how do I answer this. Many entrepreneurs do experience a certain degree of financial freedom, translated roughly as the ability to generate enough consistent money to live well in the world and step away here and there, knowing things won’t crash and burn. But, truth is, with rare exception, the key to the financial freedom doors only open after you’ve stepped up and said, “here’s a massive chunk of my own blood, sweat, tears and money. I am willing to put it at risk and potentially even watch it evaporate into thin air.” And, if you’re entrepreneurial jones leads you down the brick and mortar path, you may also find yourself on the hook for a lot of high fixed monthly costs.

That’s all cool, I’ve lived that burden for a lot of years, especially before much of my efforts moved online. The benefits for me far outweighed the risks and because I’m fairly risk tolerance and passion-driven, I’ve found ways to work through the ebb and flow of entrepreneurial anxiety that always comes.

But, it’s important to go into it knowing that you may well have to put significant money at risk for an extended period of time before you get that warm and fuzzy feeling we like to call financial freedom. This is one of the reasons, most of the people I interviewed for Career Renegade ended up “legging into” their entrepreneurial journey, building on the side, while they still had consistent cash supporting the family until the entrepreneurial venture had proven itself and was generating money.

And, like above, if there’s a way to migrate much of your entrepreneurial jones online, it’s very often way easier and faster to launch, requires you to place far less money at risk and can often move into the black much more quickly.

Freedom to do what you love, work when you want to and not be under the thumb of “The Man” – Much of this is true. You do have a lot more freedom to build your daily activities and long-term vision around passion-driven activities or causes. And, you do have much more control over what you do or don’t do and when you work or take time off.

BUT, reality check, even when you’re an entrepreneur…you still always work for someone else. Your customer or client. Doing what you love doesn’t mean people will line up to pay for your efforts. You’ve got to find the sweet spot between what makes you come alive and what people are willing to pay for. Because, in the end, you always serve someone. And, if you’re not making them happy, you’re not paying your bills.

Same goes for setting your schedule. You may choose and industry where regular hours don’t matter. But, if you want to own a restaurant or retail shop, guess what, those are 7 day a week, 16 hour a day businesses. You don’t get to choose. Here, again, if you’re interests can be satisfied through online entrepreneurship, you still have to find the passion/hunger sweet spot, but you may well have substantially more freedom in where and when you work and the world becomes your market.

2. Control.

This really ties in closely with the discussion about freedom. Because freedom implies a greater opportunity to CONTROL your own destiny, how and where you work, who decides what and when. But, as we’ve seen above, just because you’ve put yourself in the perceived role of top dog in your business doesn’t mean you really are. Whether you work for yourself or someone else, you need to get paid. That means, you need to create a service or product other people value and are willing to exchange money for. And, you need to offer it in a way that is appealing enough to facilitate the sale.

So, do entrepreneurs have more control than lower-level employees, especially in larger organizations?

Very likely yes. Because every layer that lies between you and the ultimate customer is a layer that removes an element of control. But, don’t delude yourself into thinking that when you’re at the top of your business you will have ultimate control. There will always be one person above you. And, that’s you customer.

3. Money.

We’ve talked about money above as well. You may well have the opportunity to generate substantially more cash as an entrepreneur, but not always. And, remember, a fundamental truth in business is that great rewards almost always come as the result of great risk.

We’ve seen that equation degrading more and more and people better understand how to leverage the online world, especially in the context of commodotizing and selling knowledge. But the more traditional your idea, the more likely it is you’ll need to place real money at risk in order to have the opportunity for to get real money back.

And, there will, without fail, be challenges along the way. Times you just want to walk away. Times you wished for…gulp…a consistent paycheck, so you could sleep at night. Even when, most of the time, you love what you do and you still believe in your greater purpose.

Realize, too, it’s important to lead NOT with the quest for money, but with passion. Because the quest for money won’t get you through the dips, while the quest for mad passion may. Then, work like crazy and, if needed, innovative to create unconventional ways to generate an income around the activities, culture and communities that make you come alive.

And, one last thing, there’s a lot of talk these days about setting up supposed “passive streams of income.” Before you dive headlong into that pursuit, you might want to explore the truth about passive income, especially as it relates to making passive income from blogging.

And, if you’re looking for solid advice on about the closest you can come to this vision online, you may want to explore the intersection between your passion and non-smarmy ways to make money online and have a real life by checking out people like Glen Allsopp, Chris Guiilebeau, Brian Clark and Lynn Terry. They have great information and resources in this area.

4. Cause/Passion.

No doubt, for me, one of the greatest elements of entrepreneurship is the ability to pursue a passion or cause. Something capable of serving others, having a profound impact and making me come alive. That very quest, in fact, is often the purest fuel behind the most successful entrepreneurs. In fact a recent study of pentamillionaires found that most were driven not by money, but by passion or the quest to solve a pervasive problem.

BUT, it’s also critically important to explore how you are going to leverage that quest, that passion, that cause into a business and venture that is capable of generating enough cash to live well in the world and, if necessary, support a family. Sometimes there’s a readily available answer. Often times there’s not, and that’s where you have to get hyper-creative. In fact, I wrote Career Renegade largely to answer the question, “how do I take a normally moneyless passion and wrap a living around it?”

Realize, too, that, in every professional venture, be it writing, creating a product, building a company or offering a service, there will be times you get to do what you love…and times you are forced to do what you hate. I’ve taught 100 people in a sweaty, vibing, blissed out yoga class, only to find myself cleaning toilets 20 minutes later, because in the early days of a business, I did every job. It makes it better that you’re on a mission…but cleaning toilets is still cleaning toilets.

What about the giant benefit nobody talks about?

In light of all the challenges laid out above, I am still a huge proponent of entrepreneurship. In part, because of everything I just shared, but there’s one giant benefit most people never focus on. As an entrepreneur, I get to create the culture and pick the people I surround myself with

We don’t often realize how mission critical the people we surround ourselves with are in our ability to not only thrive in business, but feel fulfilled or just love every day. In the brick and mortar businesses I’ve built, I’ve taken years to build families of people, from managers to services providers to receptionists and volunteers, who are the very people who make ME come alive. And, I’ve taken it a step further and become insanely selective with what vendors I work with and who I take on as customers, students and clients.

Because, the nature of the people you surround yourself with everyday will have a profound impact on the way you experience your life. That’s why, when I’ve realized I’ve made bad decisions, I’ve not only fired employees, I’ve also fired vendors and clients.

You cannot pay me enough to take someone else’s money when I know the interaction with that person will end up sucking the life out of me.

People matter more than you realize. So, if you choose to follow the entrepreneurial path, make them a priority.

Realize, too, entrepreneurship CAN happen WITHIN the walls of a company or organization you don’t own. I’m a big believer in larger companies fostering empowered, innovation-driven entrepreneurial pockets and projects. It’s rare, but if you have an entrepreneurial jones but would really rather work within the support structure and tap the resources of a larger entity, work to find one that supports and empowers original thought, innovation, service and freedom.

Entrepreneurship can be an immensely rewarding life, especially when things go right.

But, make no mistake, rewarding does not mean easy, certain or stress-free.

So, if you choose to enter the waters, do so with your eyes open.


Awakened Shout Out – This week, I’m following the lead of my friend, Gretchen Rubin, of The Happiness Project blog and now #1 NY Times Bestselling author (woooohooooo!!!). Here and there, I’ll be ending posts with a brief Awakened Shout Out to people who are doing cool things in the world or resources you guys should know about.

This week, I’ve been reading Dani Shapiro’s beautiful new book, Devotion, that explores big questions of spirituality, parenting and faith on a personal, real-world level. I met Dani recently at a small gathering of writer-types a few weeks back, she’s very cool, genuine and man can she write. Give it a read.

Also, just got off Skype with Ishita Gupta, who some may know as Seth Godin’s Head of Hoopla, but she’s working on a very cool project on being fearless called Fear.Less that’s about to launch soon. You can get a feel for it over at


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