“Work from home”, “be your own boss”, “make money while you sleep”

These are the words, terms and phrases that are said ad nauseam to the masses about how to claim back your happiness and do what you are supposed to do by becoming an entrepreneur.

Let me first start off by saying that coming from a corporate background and also having jobs in the service field I know what it is like to work in a store and slog away at a desk, and I know what it’s like to work for myself.

Being an entrepreneur is great. It definitely has its bonuses like not needing to wake up to an alarm clock, avoiding a traffic filled commute to work and not having to deal with colleagues that are difficult.


People forget to share the dark underbelly and cost of what being an entrepreneur looks like.

Most of the facebook posts or instagram shots make it look like a life filled with parties, conferences, exotic locations, success and fame.

I am just as guilty of this as the next person, and while there are moments when this does happen most of the time this is not reality.

What we fail to post is the rest of our lives that are messy, busy, overwhelming and brutal.

Rarely do I (or anyone else for that matter) post the moments when we are curled up in the fetal position crying because we aren’t sure what we are doing or where we are going.

Rarely do I see the picture of the person’s bank account when they are in the red.

Never have I seen the status update of the class, course or program that no one signed up for or the refunds given after a launch. And yet these things happen.



If you’re doing something you love, care about and believe in, it will make the hard moments a bit less hard because you will have a bigger WHY and a bigger personal hit for the results you make but make no mistake there is still work to do.

There are a lot of positives about being an entrepreneur but the ‘wins’ and ‘costs’ are rarely on a balanced scale.

And when looking to start something that you want we have to also consider all the turmoil that comes with it.

Recently I read that “what we get out of being an entrepreneur is not determined by the good feelings we desire but rather by what bad feelings we’re willing and able to sustain to get us to that goal” (read the full article here).

So let me break it down for you once and for all and tell you the deep dark truths about being an entrepreneur.


1) It is the hardest fucking work you will ever do

Almost everyone in my family and my life is an entrepreneur in some capacity. My friends, clients, acquaintances, siblings, parents, even my in-laws.

Many of them are very VERY successful at what they do but no matter where they lie on the scale of success every single one of them will tell you that being an entrepreneur is hard work.

Each and every one works their motherfucking ass off to get what they have and no matter what they’ve achieved there is still work to do and it is not easy.

We may pretend in our posts and speeches that it all came suddenly but the truth is you will work longer hours as an entrepreneur then you ever have in a regular job. And you will have those moments where the pressure seems so large that you will want to quit.


2) It is a lonely endeavor

Even if you are part of masterminds, have weekly calls with other entrepreneurs to connect, share and swap ideas being an entrepreneur can and will be a very lonely experience. Maybe this changes once you have a solid team that you are working with or you start a business with a partner, but if you are any sort of solopreneur a lot of your time will be spent sitting at your computer day in and day out, on calls or the web by yourself.

Even if you are feeling supported, it will still be you and you alone who will have to hire, fire, come up with ideas, figure out what to say and get out on stage or online.

There is no avoiding it. You will feel lonely and at times afraid.


3) You will fail… a lot

You are going to fuck it up. No matter how many books you read, workshops you got to, courses you take, retreats you attend or summits you sign up for you are going to fuck it up.

There will be an opportunity that is missed, an article that gets botched, a launch that sucks, a program that fails or an event no one attends. It will happen, it’s okay and it’s not the end of the world. But make no mistake if you are in-it-to-win-it there is no way you can get out without some bruised egos, big bumps and massive mistakes.

Just like playing the game of falling in love fully means inevitable heartbreak. Playing the game of the entrepreneur means the inevitable moments of failure.

No matter how honest, good, heart-centred or aware you are there will be no mercy given in this area.


4) You will doubt yourself, your ideas, your abilities and your dream

No matter how much success you’ve had in school, past jobs, relationships or hobbies becoming an entrepreneur will have you question everything about yourself constantly.

You will compare your ideas to what other people are doing and wonder why you aren’t doing better. You will begin to think that you have no talent or not meant to do this work.

You will wonder why you chose to be an entrepreneur in the first place and you will wonder if it is all worth it.

There will be moments where you will want to run away and become a potato farmer so you don’t ever have to worry about sales again. Everything that was once as source of esteem will be questioned and thought to be insufficient as an entrepreneur.

5) Your happiness and sense of accomplishment will be short lived

You will have some kick ass success. You will get that client, or land that speaking gig. You will sell out that workshop or retreat or have an awesome and lucrative launch. These things will eventually (or right out of the gate) happen.

But the glorious rush, the ego hit and the money in the bank will be short lived, because as soon as the ‘wow effect’ of that wears off you will still have a business to run and the next workshop to fill. There will be the following program to promote and the next level to get to.

Being an entrepreneur is a constant uphill climb. The views at each summit get more and more spectacular but there is never really an end. There is no place that you eventually get to. So you have to fall in love with the climb.


6) In the beginning you will screw up work/life/balance

Starting out you won’t even know what that means. You will think you do, but you don’t.

Especially if you are starting or operating a business you love and believe in, this will be especially hard.

You will go into the business for money but also have some part of yourself or expression wrapped up in what you are doing. So you never really punch out from your work. Your work ends up becoming an extension of you.

Wherever you are you will be on the lookout for opportunities, and ideas.

Vacations will become research opportunities for retreat locations. Meetings with friend will be judged on how much value they bring. Social events will be based on what you can learn and who you connect with. Even the books you read for fun will be based on some version of self-help, branding, marketing or psychology.

There is no off time from your dreams, because your dreams are part of you and thus the business will infect and infiltrate every part of your life.


7) You will struggle with money and sleep

You will not make all your money and you will not sleep well right away.

You will spend hours every day, sometimes working 80 hour weeks, to make something that when you finally put it out there won’t get you paid right away if you get paid at all.

“Being an entrepreneur is the only place you can work 20 hours a day to make money while you sleep” this is true but isn’t even guaranteed out the gate.

While it is possible to make money while you sleep and have that 4 hour work week it will take years and tireless nights to get there. You will suffer through sleeplessness based on worry or work and weeks or months of making very little money.

You will have to deal with moments where you can’t pay rent or go to that party and you will move from living paycheck to paycheck to living invoice to invoice.

There will be moments you cry, get worried and look for things to sell around your house.

This is inevitable.


8) You will be jealous and judgmental

There will be times you resent and judge even your closest friends as you compare yourself your life and your accomplishments with theirs.

Though you are happy for their success or wins, you will find yourself in a slump at times and have to fight through your feelings of jealousy when they mention their big win, sold out event, newest retreat or VIP invite. You will want to be support them but you will be too busy feeling bad about yourself.

There will also be the acquaintances you unfollow or unfriend because you are feeling down and hate seeing the pictures of their most current version of “their office for the day” on the beach or yacht while you sit around in your pyjamas. Having not showered for 2 days and staying in your house for weeks you will block them out of jealousy and low self-esteem.

You will feel justified and right for doing so.


9) You will be forced to risk a lot

Many things that you feel are important will be put at risk. You will wonder if going to the gym that day is worth missing your launch deadline when you still have so much to do. You will look at what you spend on yourself and others and question whether that should be put into better branding, marketing or sales. You will want to eat healthy but after being up till 4am creating copy you will grab that bag of chips and scarf it down for dinner.

If you are planning for a family you will wonder if it is the right time to do so and possibly put it off for when things are more stable. If you want to move away or buy a house you will think twice about the market, what it really means and if you should live somewhere else all together that has a lower cost of living.

Sometimes, you will be too low resourced to have patience with your spouse or parents and too tired to play with your kids.


10) You will make friends with depression and make peace with your inner loser

You will have so many naysayers and people telling you to give up. Many times that person will be you. You will at times fall into a dark hole and wonder if you will ever get out.

If you’re lucky you will have a friend or partner or parent that believes in you but even if they’re around there will be moments that you will have to believe in yourself without proof and out of sheer audacity. Sometimes you will be depressed and so deep in the depths of that shadow that the people who can support you won’t be able to reach you.

You will have to deal with being ‘a loser’ both internally at the level of self and externally based on your results.
You will have to learn to generate getting yourself out of the shit swamp from scratch, from within and on your own. You will learn to dig yourself out of the gutter.


This is the truth, the reality, the clear facts about the real world of being an entrepreneur. It is not said to scare you, worry you or make you afraid. It is meant to show you the claws of the dragon and make sure you still want a ride.

Success, dreams fulfilled, and a business that thrives is all there and waiting for you, the price for admission just happens to be EVERYTHING you got.

Welcome to the world of being an entrepreneur paradise awaits! But make no mistake that this wonderland comes part and parcel with an entire ecosystem of darkness and you have to be prepared for both.

The flowers here are gorgeous but they’re all still covered in thorns.