Motivation and Inspiration

Want to quit your job? The top 10 fears that keep us from making money on our own.

Do you want to quit your job to start making money on your own? Many of us dream of quitting our jobs but never pull the trigger. Our fears shackle us to the grind!

Through my blog and book, I’ve been able to connect with thousands of people and ask the question…what is your biggest fear?

The responses almost all fall into the 10 buckets you’ll find in this post.

I’ll give a brief overview of each and a quick response. Look for in-depth posts on each topic over the coming weeks!

And let me know in the comments below…have I missed your fear?

quit job shackled to day job
Shackled to your day job?

1. I don’t have time

Fear: How the heck are you supposed to start a business on the side or otherwise when your commute + job takes up 10 hours per day? When you’re not at work, is it still weighing on your mind? And what about family, social time, hobbies, and chores?

I can barely read a book or watch a TV show! How am I going to fit in an “escape the grind” venture?

Quick response: It doesn’t matter who you are–we all have the same exact amount of time. Time is the ultimate leveling field. Whether you’re…

…the cog who slugs away at a forgettable job and zombies out to TV at night…


… the “high on life” go-getter who publishes bestselling books each year, builds a real estate empire, and makes time for family…

It doesn’t matter. We all have the same amount of hours in the day. It’s about being absolutely ruthless with our time and prioritization.

Here are some great ways to find time to be an entrepreneur or side hustler.

2. I don’t have money

Fear: I have debt. Or…I have a bunch of money saved, but you have to be a millionaire to take this sort of risk. Or maybe…I’m a broke college student!

And starting a business takes a huge investment! I need office space, materials, employees, a website, and maybe even a janitor!

Quick response: It’s extremely rare for the idea and the funding to come from the same person. Knowing this means there are many creative ways to start without having any cash that don’t require debt.

That, of course, assumes it necessarily takes a lot of cash to start a “money-making machine.” The best businesses are simple and start self funding.

And by the way, if you don’t have money, is your current path going to set you free? Or will it keep you forever locked in?

Make Money from Kindle Publishing

3. I don’t have any ideas, skills, or experience to go about making my own money

Fear: I have passion and am not worried about the risks…but I’m nothing special. I don’t have any ideas. And I don’t have any skills that someone would actually pay for. Running a business? I’d have no idea what to do.

Quick response: This may be very true and it was the case for me too. In fact, I believe there are 4 skills you really need to be successful with your own small business ideas and side hustles. There are two easy ways to tackle this:

  1. Find a job (even if it’s a step down) that gives you real-world experience with the skills you need to build. Don’t get comfortable! Push yourself to kick ass at that job and then exit as soon as you’ve extracted what you need.
  2. Partner with someone who completes your “big 4 skills.”

Plus, learning is easy now. We have access to information like never before…it’s in your hands to upskill yourself. If it’s ideas you need, check out my post 13 Real Small Business Ideas and Side Hustles.

I spend a lot of time in my book Leave the Grind Behind on how to get the most from your day job before you quit.

4. I don’t believe it’s really possible to quit my job and make my own money

Fear: Have you seen the small business failure statistics? No one really quits successfully. I need to be a grownup, suck it up, and get a job that sucks my soul…just like everyone else.

Here’s a stat for you: 20% of small businesses fail in their first year, and 50% of small businesses fail in their fifth year (data from What Percentage of Small Businesses Fail?).

Quick response: This was another major struggle for me personally! We are conditioned in school and our upbringing to become working stiffs. Two key approaches:

  1. Mental practices such as meditation, visualization, and affirmations can literally transform your mental conditioning and alter your expectations for what is possible.
  2. Surrounding yourself with the right people alters your perception of reality. If you spend all of your time (day job and socially) with lifers and cogs, guess what your image of reality is? But what if you surround yourself with excited, enthusiastic people who are successfully making things happen in their lives?

Start by finding a success mentor.

Business Partnership Advantages Small Business Side Hustle

5. I fear I’ll lose people’s respect

Fear: I’m a big-time IT director responsible for multi-million dollar projects and hundreds of employees. If I quit to start a blog…everyone will laugh at me!

Quick response: Any time you do something big in life that most people don’t have the guts to, you’re going run into naysayers, doubters, and jerks. Be prepared to see people’s true colors and make some changes to your social network. Just like above, the best solution is to stay mentally focused and strong while also surrounding yourself with people like you.

6. I fear the complexity and details, like hiring employees, health insurance, accountants, and taxes

Fear: I can’t quit my job! Have you hear health insurance is expensive? And I’ll probably need a CPA. Do I need to track mileage or fuel expenses? Is QuickBooks the devil?

And if I start a small business, I’m going to need a store and employees! I need signs, marketing, shipping, and insurance. There’s no way I can deal with all of this…

Quick response: If your mind is at this level, you’re not in the right spot. Period. Before starting a business or side hustle, you should be dreaming big and reaching for greatness. Paying a couple hundred more for insurance should be an insignificant blip on the radar. Yes, a bunch of random expenses and crap will gnaw at your income. But what’s at stake? Potentially massive earning. Potentially doing something you love. Potentially building assets that will make you rich!!

I’ll say this until I’m blue in the face…the best businesses are simple. There’s nothing saying money comes from complexity. The best ideas are simple to start. Perhaps they grow big and complex over time, but that’s fine. Once you’re big, you can hire other people to deal with complexity. Challenge yourself to find simple money machines.

By the way, that stat above that says 20% of small businesses fail their first year? That jumps up to 80% if you have an employee! Another nod for keeping it simple.

small business idea keep it simple
Keep it simple, stupid.

7. I’d have to quit my day job first

Fear: If I want to start my own company, I need to risk everything! I need to quit my job and go months…or years without pay.

Quick response: Side hustle your way in! Nearly everyone I know who has made the transition kicked their journey off on the side. You can learn, experiment, and begin generating cash flow while still having the safety net of your job.

In fact, here’s a good article from Inc called Entrepreneurs, don’t quit your day job. Do this instead.

Also consider my post How to Negotiate Variable Pay, Equity, or Ownership in Your Job.

8. I’m scared of debt

Fear: I spent a bunch of money on college, and a car, and maybe a purse I didn’t need… I will never go back into debt again! And to create a business, you have to have debt.

Quick response: If you stick with the premise that the best businesses are simple, how much money do you really need? What if you are able to sell your idea or services online? Outstanding plug-and-play technologies are widely available and generally very inexpensive. Most great businesses can start lean and simple.

But eventually, you’ll want to grow and scale…something that can only be achieved with debt. Once you’ve proven your business model and can factor in “cost of money” into your numbers, debt will no longer be scary. You’ll see it as a beautiful enabler. It’s the reason nearly every successful company takes on debt. It’s just an expense, like “Facebook ads” or “rent.”

Plus, there are plenty of other options for growing your business that don’t require debt. In The Book on Small Business Ideas, I have a bonus chapter on “Going Big.”

9. I’m worried about failing and humiliating myself

Fear: If I do this, I’ll probably screw up and have to come crawling back to my boss while all of my coworkers laugh at me…and throw wadded up sticky notes. Jerks.

Quick response: Ooo…I love this one! This is FUEL to not mess up. In my article on setting anti-goals, I talk about the incredible power fears like this have. You just need to harness that fear and do everything in your power to avoid it.

If you’re failing, it just means there is something you don’t have right yet. Overnight success is usually the result of a string of failures leading up to that one light bulb that works. To reduce risk here, you can go the side hustle path and prove your concept to yourself before going all in.

And really, you’re just describing your worst case. If things tank, you go back to status quo, get your old job back, and eat crow for a few days. Is that really that bad?

10. I’m a grownup with a mortgage and family…I can’t be irresponsible!

Fear: Alright, here’s the tough problem…young people are afraid because they don’t have skills or experience…but once you have the skills and experience, you have responsibilities! So we’re all screwed.

It’s almost hard admitting you want to pursue your dreams and passions, right? It feels childish and selfish. That’s not what grown ups do.

Quick response: This was a major struggle for me too, and the solution here is very personal. There is of course saving, planning, and doing the side hustle, but at some point you have to pull the trigger. Get the support from your spouse. And go.

After all, according to a LinkedIn study just conducted about “Quarter Life Crisis,” 61% of respondents say finding a job or career that they’re passionate about is the top reason they feel anxious. So you’re in the majority if you want to pursue your dreams and passions.

But you know what finally worked for me? I figured that if I failed and spiraled my family into the mud, I could just go get a regular job. And since I gained a bunch of new experience, I could probably get an even better job than I have now. I could even go back to my same company…I left on great terms and I know they’d be happy to have me back.

So my worst case was actually my current situation at the time. Go figure.

What’s your fear?

Are you destined for greatness but have a fear holding you back? What am I missing? Let me know in the comments below!

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