The Dark Side of Entrepreneurship (& How to Love Every Part of The Journey)

Hey and welcome to episode 15 of the Free and Fearless podcast. I hope you’re having a great week, and are ready to hear some harsh truths about entrepreneurship because that’s what I’m going to talk about today.

Tune into the episode below:

Show Notes:

  • [1:37] Why entrepreneurship isn’t for everyone
  • [4:16] How to walk the path alone
  • [6:56] Challenging moments you’ll experience as an entrepreneur
  • [8:27] The 1000 days rule
  • [10:47] How starting from the bottom shapes your mindset
  • [11:57] Example of a badass bestselling author who was once broke
  • [13:50] My advice to anyone who wants to live life on their own terms


I won’t mention anything spiritual, I won’t talk about the different business models, about alignment, about creating your dream business or anything like that.

I will be absolutely realistic, more than some people might like. But here’s the thing – we can keep talking about the benefits of starting your business, of the different ways to make money online. I can keep sharing success stories of business owners on my blog, and I can keep sharing what I learn along the way and how your business income allows you to build an amazing lifestyle.

But whatever you try, there comes a moment when it gets hard. 

Even if you have the discipline, even if you think you are prepared, even if you have a community and enough support, even if you take courses, have coaches and are ready to invest.

No matter what, there is a certain point where it gets unpleasant. That’s when most people give up. If not then, many give up at the next level, when it gets even harder.

I’ve always believed that life is a series of problems. You’re doing well when you are solving the problems you’ve chosen. 

If you’re starting or growing a business, you’ve chosen this. You’ve taken the decision to deal with all that comes with it. As it is with anything else in life, there will be aspects of it that you won’t enjoy. There will be periods that nothing could prepare you for, and there will be many, many reasons for you to give up.

That’s why entrepreneurship isn’t for everyone. I know that more businesses than ever were started during the pandemic, and with everyone being at home, ready to learn and invest, it might seem like it’s easy.

You might see all those people crushing it, earning a lot in their first year, signing high-ticket clients even though they literally just became a coach. I’ve seen this too.

But the pandemic will be over, a new normal will be here, and these new business owners will have to adjust all over again. Their business isn’t yet sustainable.

One good month doesn’t mean you will sleep peacefully knowing there’s income coming for the rest of the year. And whenever I talk about business, even though I don’t earn much compared to many others, I always mean creating a freaking recession-proof business. One that is exactly how you like it, which brings you the ultimate satisfaction on a daily basis, which is literally your dream business and which allows you to have the lifestyle you desire.

So today, I’m going to discuss the dark side of entrepreneurship.

Dark doesn’t need to mean bad. It’s just not easy. But I believe that it’s necessary to build the skills that will help you deal with negativity from others, manage the money you’re about to make, develop the mindset that will allow you to stay sane and still enjoy the journey when your business isn’t growing, or – when it is growing. Because both of these can drive you crazy in ways you can’t imagine.

You’ll Be Lonely Before You’re an Entrepreneur

5 Types of Entrepreneurial Stress & How to Manage Each

You might have many friends. You might even have one of those close family relationships where every relative supports you no matter what.

You might hire people quickly and even try to build a team.

But be ready for this, cause it’s a fact: you’ll be alone in this.

It will just be you, late nights of hard work (for months and years!), not seeing understanding in other people’s eyes and being perceived as someone hustling on a hobby that will never become something more.

The lack of understanding can’t stop you, though. So if you let it, you still haven’t realized a few things.

For instance, we live in a non-understanding world, and that’s okay. Everyone’s looking at things from a different angle. And because one thing is sure and it’s that you’re different, expecting them to understand the unconventional way of living you’re doing isn’t realistic.

Then, there’s the fact that other people will interfere if you share your vision, and maybe that’s why you’re better off keeping your goals to yourself. At least until you see results.

I think that you don’t actually need support on your entrepreneurial journey. It’s all an outer factor. And the real qualities that will one day make you an independent worker having control over your life, are within you. Other people have nothing to do with that, and that actually makes the process easier.

Be okay with being alone. Don’t overthink it. Love the solitude when it’s just you, your laptop, and the doubts and confusion, as you’ll have no idea where this might take you and how long it will take.

One thing is sure though. It will be a better place than the average life planned for you.

Also, you have all it takes to achieve it. To be patient enough to give it years. To be mentally strong to handle the lack of understanding and support. And realistic enough to let go of expecting others to have anything to do with this, or expecting easy solutions to come out of nowhere.

In my hardest moments, even though I had people wanting to show support, trying to take me and my work seriously, and wanting to help, that had little to do with the transformation going on in my mind.

It’s a path you walk alone, and that’s how it should be. Cause once you walk it long enough, the world is yours. 

In my loneliest moments, it was just me and my writing, then blogging and then the many other forms of content creation related to my business. Writing is my passion, so it’s also all I needed to stay sane and keep going. 

You’ll Be Stressed Before You’re an Entrepreneur

The real face of entrepreneurship includes some or all of the following moments (at any stage of your self-development journey and business creation):

  • teaching yourself what internet marketing is all about, learning how to create and edit audio or video for a product you’re working on, because you can’t afford to hire an expert;
  • falling asleep thinking about the next steps you should take;
  • waking up and opening the laptop;
  • answering emails while spending time with family or friends, and having to deal with tech issues or customer support while on a vacation;
  • never actually having some time off of your side hustle for a year or two;
  • not knowing if you’ll make it or not;
  • starting to think you’ll need to get a real job again if you don’t make more money any time soon;
  • worrying about all kinds of stuff that normal people don’t need to worry about;
  • there’s no such thing as clearing your mind to enjoy another activity – you need to be focused on your project only, as it’s the foundation of the financial freedom you’re after that will turn your whole life around;
  • waking up without a smile on your face, but knowing it’s all for a good cause;
  • not enjoying the nice weather outside, as you’ll need to be inside reading about digital skills you never thought you’d need to learn;
  • turning branding, networking and a few other activities into a free time thing – meaning, something you do whenever you can.

The time all this is taking is stressful too.

There’s something called the 1000 days rule in business. And it says that ‘you’ll be doing worse than you were at your job for 1000 days after you start your muse business’.

Also, each of your customers is now your boss. Or at least that’s how you should treat them. They are helping you pay your rent or mortgage. Without them, you’ve got nothing and might need to get back to your old life which will make you miserable.

Having so many bosses is stressful. You often need to be available 24/7, depending on the kind of work you do. To answer the same questions over and over again (until you find ways to automate the process and skip the repetitive tasks). To be asked to do more than what you’re being paid for. And much more.

That’s another level of stress and you can handle it. Because the stress of not designing a life on your own terms is worse for people like me and you.

There are also business mistakes you can make that can make you broke.

How do we handle that?

By being absolutely sure that we’re not made for a regular job, desperately seeking the freedom only a lifestyle business can provide, and knowing we have something we love doing and there is a way to make money online and help people with it at the same time.

Your coffee won’t taste as good in the morning knowing there’s something to fix on your website that’s preventing payments from happening smoothly. And it might take hours of research to find out what the problem is.

You won’t enjoy shopping anymore, knowing how important every dollar is, how hard it is to earn online, and planning what better things you can invest in.

When others around you are talking about things from daily life, what’s going on in the world, or their next trip, you’ll be validating business ideas in your mind, trying not to lose hope and reminding yourself it’s exactly what all other entrepreneurs have done back in the days.

But guess what?

That’s what will make you one of them. All these little things that stress you out now, and that will be your stressors for a long time, are how the mindset of an entrepreneur is shaped. And it’s a beautiful process, if you ask me.

Read also: 5 Types of Entrepreneurial Stress & How to Manage Each

You’ll Be Broke Before You’re an Entrepreneur

Strategies Traders Can Use to Grow Their Investment Portfolio

Ready to be broke?

Let’s talk about having less money than you’ve ever had before.

First things first, though. Some people create a brand online without even realizing, be it a YouTube channel that gets many views in the first weeks, a post that goes viral, or landing a client that pays all the bills and you don’t need much else in the beginning.

These people start making money at a young age, or can quickly leave their 9 to 5 and do that full-time. And that’s okay.

But that’s not me. It’s not you. It’s not Tony Robbins, Mark Zuckerberg, Jack Dorsey, Mark Manson, Corbett Barr, Thomas Edison, Elon Musk, Nathan Chan, Henry Ford, or anyone else who simply worked their ass off and started from the bottom.

And you know what?

That’s the best way you can have it. To start with nothing, to leave behind the old mindset and lifestyle, to completely dedicate your time and energy to the things that will make you an entrepreneur, embrace the uncertainty and risks and understand the real meaning of hard work.

I wanna give you an example.

I’ve been reading Mark Manson long before he became popular with his bestselling books. I loved his work and way of thinking back when he was a blogger, before I started my business. His early days, way before he was living the good part of doing what you love and making money from it, looked like this:

‘I figured between my savings, my meager monthly income, and living frugally, I could sustain myself for at least a year while I built up my new business, which was more than enough time to get on my feet. So it was with confidence that I put in my two weeks notice at the bank. That was June of 2008…

By January of 2009 I was broke. The clients in Boston had dried up. I built a website that nobody visited and wrote a book that nobody read. Working alone sucked. Nobody took my job seriously.

But I never considered giving up, not for a minute. I loved what I was doing. And I loved how I was living. That and I could see that the potential pay off of financial independence and mobility was worth it, no matter how difficult the struggle was. I moved in with my girlfriend the next month who proceeded to support me for much of 2009. In September we broke up. So at age 25, I moved back in with my mother for the remainder of the year.

I refer to 2009 as my “Pain Period” — 16 hour days, sometimes more, for about a year straight. Crash courses in branding, copywriting, sales, product design, search engine optimization, social media, etc. Everything self-taught. I didn’t have any money to hire help, so all web design, product creation, marketing, promotions, advertising, was done by me.’

So, how do you feel about going through that?

If you’re scared of such a reality, prefer the comfort of your current lifestyle and the fake security that your job gives you, alright then. That’s how you should keep it. 

But if you want to be out of the system and play by your own rules, and – more importantly – if you have something you’re passionate about and need to turn it into something more as that’s the only way to find meaning, then go for it. 

Go for it with all you have. Cause there are few other things in life worth that much of your time and energy.

Be broke for some time. It teaches you lessons. For a start, you realize you don’t need to have most of what you consider necessary. Then, there are ways to survive without cash.

If you get over such periods of being broke and still keep hustling on your business, you can get through anything else in life.

To be a visionary, means to be accepting the bad sides of it now, but keep working on what you believe will support you for the rest of your life. If that’s what you gain, a year or two of your life dedicated to hard work and entrepreneurial stress is worth it. In fact, it’s an element you can’t go without if you’re serious about making this lifestyle change.

Entrepreneurship isn’t a whim. It’s what you’ll become and this new reality isn’t something you’ll take a break from. Most probably, ever.

Plus, there are some pretty smart ways to live frugally, and still have an enjoyable daily life while building your online empire.

Final words

A popular saying goes like this: find what you love doing and you’ll never work a day in your life.

You know what? I believe it’s the opposite.

Do what you’re passionate about, turn it into your career, and you’ll be working every day for the rest of your life.

But work doesn’t need to have the negative meaning society has given to it over the last decades.

Instead, it’s what shapes you, helps you feel productive, lets you make a difference, and gives you the dream lifestyle – which is life on your own terms.

I hope you enjoyed this episode of the podcast and article. Share your biggest breakthrough with me on Instagram and tag me @letsreachsuccess. If you think there’s anyone else who can benefit from what you just heard, then share that episode with them too.

Learn About the Dark Side of Entrepreneurship nobody talks about
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