The truth about entrepreneurship

May 4th, 2016, on the phone with S*: “I’m going to close my business and get a real job. I’m done” she tells me. I’m shocked. S* is very successful in a competitive market.

She goes on to explain that she’s burnt out, and has been for a long time. She feels that the physical, emotional, and spiritual cost of running a business is no longer worth the freedom and income it generates.

As I listen to S* speak, I notice something unexpected: I’m jealous. A very real part of me wishes for a real job too.

A few days later, I mentioned all of this to a famous entrepreneur. After pausing for a while, he quietly said, “I wish I had a real job too.”


I started my first business as a professional magician when I was six. By the time I was 18, I was performing for Fortune 500s and professional sports teams. Since then, I’ve built three other businesses. Two succeeded, one failed. I’ve also consulted for hundreds of entrepreneurs and executives in every stage of the game.

It’s easy to get swept away by the romanticism of entrepreneurship. It seems like building a business is fun and exciting and that owning one creates a lofty life.

In reality, entrepreneurship is not nearly as glamorous, fun, or easy as most have been led to believe.

In this article I’m going to unpack the truth about entrepreneurship as I’ve experienced it, both as an owner and an advisor. We’ll cover the good, the bad, and the surprising. I’ll help you figure out if being a founder is likely to make you happy and explain how to increase the possibility of success while maintaining as much sanity as possible.

The good

You gain control of your time and focus. When you start your business, you will be its slave. It will demand far more from you than you expect. This will last anywhere from 6 months to several years.

If you’re able to push through, something amazing happens: you gain almost total control of your time and focus. This creates the potential for a deeply engaged, vivacious life. The ability to drop what you’re doing to see a friend, hop on a jet, or take a personal day with very few repercussions is amazing. For many, myself included, this alone makes the struggle worth it.

You get to choose how much money you make. In fact, doing so only requires developing three things: a product or service that people want, a way of letting people know that it exists, and an effective sales process. Sales and marketing are easier to learn than you expect. The hard part is developing something that people will enthusiastically purchase (more on that in a moment). Once you’ve done that, your income will directly correlate with the amount of energy you invest in your business.

Be aware that the ability to choose how much money you make is also a trap. Many people become enslaved by the desire to make as much money as possible. To do so is to waste your life.

The bad

You will sacrifice your mental health: Six months ago, W*, a very successful non-profit founder, asked, “Do you think it’s possible to build an organization without hating yourself at least some of the time?” My honest answer: no.

If you decide to start a business, your mental health will suffer. Rejection, disappointment, extreme stress, isolation, embarrassment, and intense self-doubt are woven into the fabric of entrepreneurship. I know this sounds like an exaggeration. It’s not.

Here’s one example (of many) from my old speaking business; every entrepreneur has a similar story.

McGill University was hosting a global leadership conference, and I was on the short list of keynote speakers they were vetting. To my delight, they decided to hire me.

I sent them the contract and told my friends and family about the deal.

Several days later, McGill called back. They found a famous speaker who was willing to work for free and decided not to hire me. For several days, I was miserable. I had no interest in seeing my friends, I couldn’t focus on work, and my belief in myself was shaken to the core.

If this only happened once or twice a year, it would be manageable. But this happened once or twice a month and went on for several years. Of course, it was intermingled with just enough success to keep me going, but it was a true struggle.

Unfortunately everything about that story is normal for entrepreneurs. Your self-worth gets tied up -almost entirely- in the performance of your business. As it fails you’ll feel crushed. It will take everything you have (and perhaps a bit more) to pick up the phone and take a shot at your next sale.

As you build your ability to generate leads and close deals, you learn to trust yourself without getting attached to outcomes. For most, this will take several years, but if you pay attention to the process, you’ll notice incremental gains, which will boost your confidence. Until then, it’s normal to feel bipolar as you revel in each new victory, while crumbling with each new defeat.

Isolation is a normal side effect of entrepreneurship: the sheer act of blazing your own path in life is always isolating. It means that fewer and fewer people will be able to relate to what you’re experiencing, and the more you succeed, the fewer peers you’ll have.

Aside from that, almost all new businesses require tightening the belt, which often leads to social isolation. When I was starting out, I’d tell my friends I was too busy to hang out. In reality, I felt like I couldn’t spare $3.00 for a beer. The sad part is that some of those friends stopped calling.

The unexpected

Despite appearances, most entrepreneurs are making a middle class income. Many business owners have become adept at appearing far more affluent than they are. I did this during my first four years as a speaker. I’d act casual as I picked up a tab for my client while secretly fearing that I wouldn’t be able to make rent. I did this because I felt like I needed to appear successful in order for clients and potential clients to trust me. I also wanted my friends and family to admire me.

This type of behavior is common among entrepreneurs. I recently had dinner with the owners of two well-regarded marketing firms. I asked how much they make per year, expecting them to be well into the six-figures. Nope. They were each making about $60,000. One of my friends runs an international software company that services Fortune 500s. He employs eight people. He made $47,000 last year. Another runs an elite cyber security company with 18 employees. He made $41,000 last year.

Are there business owners out there making millions? Of course. But they’re far less common than you’d imagine.

Luck and privilege are deceptively important factors for success: anyone who claims that luck isn’t a major factor in success – and especially quick success – is delusional.  Anyone who denies that being privileged makes success substantially easier (whether that’s through economics, education, family support, gender, race, or other means) is ignorant to how our world works.

Countless self-help and entrepreneurship “gurus” claim to have uncovered the secret to success (or productivity, or profitability, or whatever). That’s a great way to sell books and trainings, but it’s also BS. Luck and privilege make a huge difference and influence almost everything in your business.

Successful people tend to assign undue credit to themselves for both victory and defeat. It leads people to believe that they have more agency than they really do. Don’t get me wrong, you’re responsible for the effort that you put in, but in most cases, you won’t actually be able to control the results.

When you succeed, express gratitude to the fates. When you fail, express compassion to yourself.

Owning a business is not as glamorous as it seems: the bitch work will always outpace the glamor. In fact, it’s a willingness to consistently do the bitch work that makes people successful.

A huge amount of your time will be dedicated just to keeping your shit together: when you work for yourself, every single decision comes down to you. You will also be responsible for managing a near infinite number of details. Staying sane and organized is half the battle.

Success does not lead to contentment. Many people believe that once they achieve their goals, they will be content. Unfortunately, it doesn’t work like that. Contentment and success are two different skills that don’t have much to do with one another. Success is about achieving your goals. Contentment is about learning to desire that which you already possess.  

Should you start a business?

If you’re thinking about starting a business, my advice to you is simple: if you can be happy doing anything besides starting a business, don’t start a business. For most people the price isn’t worth the cost.

However, if something deep inside of you is yearning to build a business, or if you need the freedom that comes alongside owning your own business, honor that. It will be much more challenging, and much more rewarding than you could ever imagine.

Protips for those starting businesses

For most people, it’s best to work on your business at night and on the weekends. Once the business becomes viable, then you should quit your job.

Get a mentor: the singular best tip I can give you if you want to become an entrepreneur is to find a mentor. While there are people who offer this as a professional service, it tends to be more effective as an informal relationship. The best way to foster this relationship:

  • Find someone who you want to be like in 10-15 years.
  • Email her. Tell her that you admire her and ask if she would be willing to chat for 20 minutes. If possible, propose meeting in person. Make it easy for her by offering a variety of options, including meeting at her office.
  • When you meet, come prepared with broad, open-ended questions about how she became successful. Make sure that she’s doing most of the talking.
  • After the meeting, send a thank you card.
  • Follow her advice, even if it doesn’t make sense.
  • Several months later, update her with your progress. If she responds, ask if it would be possible to get together again.
  • Rinse and repeat.

The trick is to show her that you sincerely value her time and are following her advice.

In the beginning, focus exclusively on product and sales. When you’re starting out, social media, a cool logo, a flashy website, and networking groups are huge time wasters. All that matters is building a product or service that people want and learning how to sell it.

This raises the question, “How do I know if people want my product?” The answer: create a basic version of your offering, and try to sell it. Let’s say that you want to create a new type of chalk for rock climbers to put on their hands. First, make a batch of the chalk at home.  Show it to a few rock climbers and ask if they’d like to buy it from you. If people buy it, you’re on the right track. It’s important to pay attention to what they do, not what they say. If people aren’t buying, they aren’t interested. Pitch your product to at least 50 buyers before attempting to judge whether or not it’s viable.

Over time you’ll refine your ability as a salesperson. Reading books on sales will help speed up your success, but if all you’re doing is reading (and not actually selling), then you’re doing it wrong.

Create or join a mastermind. Running a business is isolating and difficult. One of the best ways to cut through the isolation while also speeding up your success is to join a mastermind.

A mastermind is a small group of people who meet on a regular basis to invest in one another’s success. The mastermind that I am a part of consists of four entrepreneurs. We meet on Monday mornings. Each week we check in with one another, offer solutions/perspective on the problems we are facing, and make a commitment for the following week. The three people in my group have become some of my closest friends and most trusted advisors. Their guidance has improved every area of my life.

You can create your own mastermind by finding a small group of entrepreneurs and meeting with them on a regular basis. During your meetings, everyone should be open, honest, vulnerable, and willing to help.

So, why haven’t I gotten a real job?

August 2nd, 2016, back on the phone with S*: “How’s the new job going?” I ask.

“I hate it. I think I’m going to quit. I like having a steady paycheck but I can’t stand my boss. I miss being able to pick the projects I work on.”

“So are you going to look for a new job?”

“No. I’m going to start a new business. I’ve got a few ideas…”

At the top of the article I mentioned that I sometimes find myself wishing for a real job. And yet, I choose to ignore that wish.

I’m one of those people who is happier working for himself despite the significant toll that it takes. Yes, I could figure how to be ok working for a boss, but it would feel like a betrayal.  I get restless and depressed when I’m forced to work on projects I don’t love.

In 2009, my mentor said to me, “Jason, your curse in life is that you are an entrepreneur. It’s your job to figure out how to make that a blessing.” Those words still ring very, very true.

Sign up to receive Jason's expertise in your inbox.

Thank you for reading. Sign up to receive the Self-love & Self-Compassion Checklist. You’ll also received articles on the latest strategies and tactics for improving your mental health, mindfulness, and well-being.

I take your email privacy seriously.

15 thoughts on “The truth about entrepreneurship

  1. The highs are high the lows are low. The pay scale is not so cut and dry. A lot of entrepreneurs do not pay themselves a lot but do control assets and has other economical benefits.

    1. Colby – you’re right about the pay scale and asset manipulation. There are some entrepreneurs who intentionally keep their salary low, and then use tax loopholes to pay huge dividends to themselves or command company assets for personal use (which depending on the business’s structure can be surprisingly legal). Even with that possibility though, the overwhelmingly normal experience for entrepreneurs is to make a livable but not substantial income. And I feel ya on the high highs and low lows – those pretty much defined the first few years of my business (and define the entirety of many people’s businesses).

  2. Excellent article, though a bit depressing! I’m a social entrepreneur and started up an NGO in a very challenging country, and I totally identify with the words about isolation. In my case, of course, it’s not about earning money as you certainly don’t do this kind of work for personal income generation but my friends tell me that I am spiritually wealthy!

    1. Gwen, thank you! And more to the point, thank you for the work you’re doing. The world needs more people like you. As you’ve assuredly figured out the best way to improve the world – if you’re an entrepreneur – is to use you abilities in direct service of the individuals and communities that need it. Honestly, making money is easy when compared to the work you’re doing. I spent a few years volunteering and consulting for NGOs. It was among the most difficult things I’ve ever done, though also, easily the most important. I hope you feel spiritually wealthy, and again, thanks for using your gifts in service of the less fortunate. 🙂

  3. Just started my business this month and it’s actually going pretty well. Thanks for this ! I was just saying I should go back to my old IT job.

    1. Christina – congrats on your new business. 🙂 If you’re enjoying it and have the financial means to stay afloat, give it time to prove itself viable or not. Very very very few businesses become profitable within a month.

  4. Great article Jason!

    I own a small gym and recently just also “got a job” … But the job I got is challenging and my colleagues and co-workers AND boss are amazing people.

    You put entrepreneurship into words very well. Thanks for the article!

    1. Thanks Ronny, I really appreciate that. If you can balance it, I actually like the small business + job model for most people. Also, I’m CrossFitter too (Elevation in Denver). Your gym looks awesome!

  5. Genuinely Great Article. I get so many of these ridiculous Forbes articles in my news feed like “I quit my job and now I travel the world and pay myself and you suck.” Your story is what people should be reading; it’s nice to get a little more detail than “It’s hard, but it’s worth it”. Thanks!

    1. Thanks Brian, I really appreciate that! And yeah – I feel ya. The conversation about entrepreneurship has been blown wayyyy out of proportion. In fact, earlier today I told one of my friends, “Entrepreneurship is just bad for your mental health, at least in the beginning.”

Comments are closed.