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June 21, 2021

The Disadvantages of Entrepreneurship

Andy Hill

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In January 2020, I decided to make the leap to a life as a digital entrepreneur. There were very few thoughts in my head about any disadvantages of entrepreneurship. I was mainly looking at the positive side of it all.

I had been working in corporate event marketing for 15 years and decided it was time for something new. My zest for my career had faded and I had found a new passion that I was very excited about. 

For the previous 4 years, I was slowly growing a business in my spare time outside of work. It started out as a hobby, turned into a side hustle and by the time I made the leap, this was now my full-time gig. 

I use the words “full-time gig” sparingly because I’m not really working “full-time” anymore. With my wife moving back to her career full-time and away from her stay-at-home mom duties, I’ve jumped in with a lot of the household and kid duties. Shuttling the kids to and from school each day, packing their lunches, helping with homework, soccer Dad-ing, ya know … all that type of stuff. 

So lately, I’m kind of a half-time entrepreneur and half-time Stay-at-Home Dad. 

Of course, the pandemic threw all those “roles” out the window for an EXTENDED period of time, but things are getting back to normal now. 

BUT I do look back at what I used to do and the salary and benefits I had and wonder… Did I make a mistake? 

Did the glory of “going out on my own” and “doing my own thing” get me so excited that I didn’t think long term enough? 

Let’s review the disadvantages of entrepreneurship vs. being an employee (and I'll share some pros as well):

Con #1:  Making Less Money (a lot less)

Andy Hill interviewing Ally

During my career, I was able to grow my salary immensely. My last role had my salary around $180,000

All I had to do was sell stuff and make clients happy. Was it hard? At times, it was difficult, but mostly, it was something I was skilled at and therefore, I should have been happy. But I wasn’t. 

I really didn’t enjoy what I did. 

Today, I pay myself a salary of around $36,000 to run my business as it’s sole employee. If I perform well, sell stuff and make my clients happy, I’ll consider giving myself a raise.

But for now, I’m in growth mode and therefore, I need to keep investing time, money and resources into the business. 

I hope to make more in the future, but it is what it is. With my wife working as well, we have about $6,000 take home each month. That’s plenty for us to live on right now. 

Related Post: The 10 Steps I Took To Quit My Job and Become an Entrepreneur

Pro #1:  Time Freedom

 The counterpoint to making less money is that I’ve earned so much more time back in my life. 

Right now, I’m working between 10:30am-3:30pm each day. After the kids are off to school, I exercise every day. I’ve never felt so healthy in my entire life. 

When I want to take a vacation, there’s only one person I have to ask … Me. 

Yes, I still have to get my work done, but I’m in control of that work. I’m in control of what I want to do with my time. And I love that. 

When I was side hustling this small business of mine, working in the evenings and weekends was must. Now that’s a rarity. 

I’ve prioritized more of my time toward my family as a soccer coach, a PTO treasurer and a Dad who is there. Life is good right now. I’ve never been happier. 

Con #2:  Complacency Isn’t an Option

Typing on laptop

There were times in my career when I was working hard, driving sales, leading teams, and making my employer proud. And there were other times when I wasn’t as much of a go-getter and I wasn't exceeding my goals. 

The awesome thing about being an employee is that I still got paid the same amount of money either way!

That is definitely not the case with entrepreneurship. If I’m not hustling during my 20-25 hour work week, then I’m not making money. 

And even though Nicole and I prepared well for this entrepreneurial leap, we still need to make money to live. So if Daddy isn’t earning, we’re hurting. 

I’m so thankful that Nicole got a great job with excellent benefits. That has taken a lot of the pressure off. We’re a good team together. 

In short, without her and my drive to see this business grow, we wouldn’t be doing so hot. Complacency is not an option. 

Related Podcast: Entrepreneur vs. Employee: Which is Better? [Bread & Wine]

Pro #2:  I Love What I Do

For the longest time, I did not like my job. It was a fine industry with fine people, but I was so done with it. 

I fell into it out of college based on an internship opportunity I got from my Dad (thanks Dad!). It was fun because I traveled a lot and I met a lot of younger people like me to hang out with. 

Once I had a family, I realized it wasn’t the best career for me. At that point though, I REALLY needed the money. I was a Dad. I was a husband and I needed to provide. 

For the next 10 years, I grew my career, my position, and my salary the best I could. And it worked!

We became millionaires in our 30’s, we paid off our mortgage early and we’re now in a position to coast into retirement based on our savings thus far. 

I’m thankful for all that. Truly. 

But I was done with my job, my industry and the emotional grind. 

Today, I absolutely LOVE what I do. I get to help people win with money. That’s fun to me. 

Every other week, I interview REALLY interesting and intelligent people that help me to grow. 

I can’t tell you how much I’ve learned from doing my podcast. Definitely more than I learned in my 6 year MBA program!

So I may make $140,000 fewer dollars per year, but I wouldn’t trade it for the world. I love my new job. 

Con #3:  Entrepreneurship Can Be Volatile


When I decided to leap from my 9-to-5 job, I did it with a few parachutes packed away (outside of the financial and emotional support from my wife):

  • $100,000 in savings
  • A paid-off house
  • And a sizeable contract from a client

The savings made me feel comfortable knowing that we could always dip into it if needed. 

Paying off our mortgage early gave me confidence in knowing that we’ll never lose our house. 

The client contract helped Nicole and I know that my income would be solid. Even though it was a lot less than I was making in my full-time job, it was an excellent starting contract. 

Unfortunately, a little global pandemic came rolling through in my first year of entrepreneurship. That contract was canceled due to loss of revenue after about a half year of working together. 

This was a HUGE blow to our family’s income, my company’s overall revenue, and my mental health. It was a tough one to come back from. There were sleepless nights and even some tears … I was feeling low. 

But after some time, some advice from friends and family, I realized that this experience was a blessing. 

I’m no scientist, but I believe global pandemics are pretty rare. So if I can make it through this in my first full year as an entrepreneur, then I’ve got a good chance of succeeding. 

Since then, I’ve diversified my clients, opened up several new income streams and my small biz future is looking bright. 

Pro #3:  The Sky is the Limit

I do think about the great salary I used to have and I get a little jealous of “Employee Andy”. 

After my jealously subsides, I get motivated and I think … “Can’t I eventually make more than ‘Employee Andy'?”

Learning from and seeing many of my digital entrepreneur superheroes, I not only think it’s possible, I think it’s an inevitability. 

I have the drive. I have the will. My heart is in this. 

Here are some of the heroes who’ve inspired me along the way: 

  • Crystalee Beck makes over $100,000 per year as a writer and agency leader working only 20 hours per week. 
  • Kelan & Brittany Kline make over $250,000 per year blogging and work together on their small business
  • Tiffany Aliche started off unemployed and broke and now runs a $10,000,000 digital business

I’ve had the chance to interview these folks and many more who’ve inspired me to grow and win for my family. 

And, they love what they do. They are helping people and getting paid well doing it. 

Final Thoughts on Disadvantages of Entrepreneurship

Growth, work-life integration, and happiness. That’s what I’m striving for.

But even if I don’t make another dime, I’m happy. I love what I do and I’m making enough money for our family to enjoy our lives to the fullest. 

Without a mortgage, our $72,000 take home is plenty for us to live full and happy lives. So anything on top of this is just gravy. 

Gravy does taste really good though so I’m going for it. 

Where’s the ladle?!

What would you add to this list of disadvantages of entrepreneurship? How about the advantages?

Please let me know in the comments below.

Andy Hill

Andy Hill is the award-winning family finance coach behind Marriage Kids and Money - a platform dedicated to helping young families build wealth and happiness. With millions of podcast downloads and video views, Andy’s message of family financial empowerment has resonated with listeners, readers and viewers across the world. When he's not "talking money", Andy enjoys being a Soccer Dad, singing karaoke with his wife and watching Marvel movies.


  • Thanks for writing this up, Andy.

    As someone who loves PF content creation, writing, podcasting – yeah, this thought has gone through my head too. If I “took the leap”…what would I gain? What would I lose? And would it all be worthwhile—and feasible? I’m still nervous about it and therefore clinging onto corp 9-5.

    But I appreciate you laying out the pros and cons for us.

    All the best,

    • I appreciate the comment Jesse! There’s no one right answer here. I hope you’re able to find the path that works best for you.

  • Love what you do and you’ll never work a day in your life. Congrats on your ongoing success, Andy. The journey you’ve chosen is brave and, obviously, very rewarding. You are an inspiration.

    • Completely agree! I’m loving my work so I look forward to Mondays now 🙂

      Thank you for helping me grow my career and have the fortunate life that I do have Dan. I am very grateful!

  • I always appreciate your authenticity Andy! Great thought provoking piece, cheers my friend!

    • That means a lot JK! Thank you. It’s not always sunshine and rainbows. I think the rough journey is what makes the victory that much sweeter.

  • It’s a tough one for sure in the beginning. Lots of doubt. But if you’ve got investments, and you’ve got a path forward, then you should be good to go. He also said you are a millionaire, so that’s another benefit!

    Not as stressful becoming an entrepreneur if you are already worth a lot. That’s one of the reasons why some of the richest people in the world are so rich. They had massive safety not to take risk.

    So enjoy!


    • Thank you for the words of encouragement Sam! I’m really enjoying my work and I’ve figured out ways to grow my salary in the past. I’m confident I’ll be able to do it again.

      Leaders like you have helped show the way. Thank you for collaborating as you have in the past! I appreciate it a lot.


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