Is Your Current Success Preventing You From Succeeding as an Entrepreneur?

For many people, success as an entrepreneur is this mysterious, elusive milestone.  At times, it seems impossible, despite your good ideas and effort.

But then, there are those people who make it look so easy.  They aren’t geniuses.  They don’t have some unique, multi-million dollar idea.

So what’s going on here? Why them, and not you?

I’ve come to the realization through the dozens of interviews I’ve conducted (actually, we’re approaching 100 interviews now on The Daily Interview) that one of the biggest barriers to entrepreneurial success is…existing success.

If this sounds a bit confusing, allow me to explain.

The Benefit of “Unfortunate” Circumstances

Ignore for a moment the people who were “born” as entrepreneurs.  You know, the people who were building multi-million dollar companies as a fetus.  But seriously, there are many successful entrepreneurs who only know entrepreneurship (and have never worked a “normal job” before).

Ignore these folks for a moment.

What you’re left with are a lot of people who became entrepreneurs as a result of some unfortunate (perhaps even chaotic) circumstance.  As I’ve found with many of the entrepreneurs I’ve interviewed, they started their businesses (or “side hustles”) simply because they weren’t making enough money at their day job.

In some cases, this is due to having a college degree that doesn’t translate to a well-paying job out of college (i.e. many liberal arts degrees), but in others, it’s simply because they don’t feel they earn enough to support the lifestyle they desire.

And it’s not always about money either.  Sometimes, they hate what they do (especially if being forced to work a job that doesn’t align with their area of interest/study in college), or they hate the people they work with. There are a number of possible factors, but one way or another, they’ve been unsuccessful with their current employment situation.  For a lot of these people, this is what really lights the fire for entrepreneurship.

But beyond motivation, their current “unsuccessful” conditions set a much lower threshold for the success required to make the leap to entrepreneurship.  For example, if you’re making $35,000 a year at an entry level job that you hate, right out of college, it’s going to be a lot easier to make that leap to your own business compared to a lawyer who has spent 7-8 years in higher education and now earns a 6-figure paycheck.

So, back to my original questionIs your current success preventing you from succeeding as an entrepreneur?

Personally, I think that’s a big factor in my life.  Although I’ve only been out of college for 6 years, I’ve built a solid foundation in my career and now work a job that pays very well and isn’t overly stressful.  This is great, and it’s something a lot of people strive for.  But from an entrepreneurial standpoint, it makes it that much harder to build a business that I can deem “successful.”

In order to get to the point where I can feel comfortable replacing my job (which I currently have no plans to do), I need to really bust my ass with my online projects.  In a lot of ways, I need to work even harder than the person who hates their low paying  job, or even the person who was unfortunately laid off.

It’s weird to think about it that way, but it’s true.  Comfort can be a dangerous thing if you’re trying to build a business.  You need that fire. You need the “threshold for success” to be lower, so you can reach it quicker.

For truly successful entrepreneurs, the “threshold for success” isn’t fixed. It’s always creeping upward.  Even if you started as someone who was laid off and just need to scrape by and make ends meet with your basic living expenses, that doesn’t mean you’re done once you’ve reached that point.  The threshold keeps increasing, and with it, so does your level of success.

But that initial threshold – that’s what holds a lot of people back.

There’s No Substitute for Hard Work

Although being successful may be what’s holding you back, don’t think for a moment that being unemployed and having a “fire in your belly” is all it takes to succeed as an entrepreneur.

Working hard and being persistent is probably still the #1 driver for success.

In fact, the reason some people are unemployed (or work a low paying job that is “below” them), is because they didn’t work hard enough in the first place.  Or they simply aren’t motivated to do much of anything.

These people won’t magically find a way to be successful in their own businesses, because starting and running a successful business typically requires a lot more work than being a low-responsibility employee.

So How Do We Resolve the Problem of Being “Too Successful”?

I’ve given this a lot of thought over the years.

As I said before, people with lower paying jobs (or jobs they have no interest in) have an easier time quitting their jobs.  It would be foolish of me to do the same thing, especially now that I’ll have a big mortgage payment soon (and other expenses that come with having a job that affords you that lifestyle).

What are some possible solutions?

1.  Lower your standard of living and build a financial cushion.  

Here’s an opportunity to use your higher income to your advantage.  Sell your home and your car.  Buy a less expensive car, rent a cheap apartment.  Don’t go on any fancy vacations.

Get to the point where you’re saving a substantial portion of your income (50%+) and build yourself a buffer that allows you to live without a steady income for a year (more or less depending on your comfort level).  Because you’ve lowered your standard of living and are saving at such a high rate, it will be fairly easy to build that buffer.

Once you’ve done this, you can quit your job, take your “fire” and hard work ethic, and actually build a business not only because you want to, but because you need to (given that you don’t have a job!).

2.  Become a complete workaholic.

A lot of people seem to choose this route – you work 8 or 9 hours a day at your normal job, and come home to spend another 4-6 hours working on your business.

It’s easy enough to do when you aren’t in a relationship and don’t have a family.  Hell, some people do this even when they do have a family.  Again, it’s a temporary sacrifice in order to achieve your goals.

If your business succeeds, you can quit your job.  If your business fails, you at least still have your day job, and your financial situation hasn’t been impacted too negatively.  Not a bad option for those who are willing to work a lot.

3. Grind away at your goal, little by little.

This is another popular one, and it’s the most feasible option for those who aren’t in a hurry and don’t want to put too much of their lifestyle at risk.

The biggest downside is: you may never reach your goal.

This is the path I’ve taken, and I’ll be honest, it sometimes feels like I’m running in place.  There have been some small wins here or there, but I still haven’t succeeded in building anything too substantial. With that said, I still believe I will eventually get there, and I’ll be able to do it without sacrificing my lifestyle (both my standard of living, and time with my family).

This is a pretty manageable option if you can tolerate your current job and you aren’t in a big rush.  Just beware – this is by far the slowest option.

So What Do YOU Think?

This is obviously all my opinion, as I’m sure many of you have experienced something different.

What’s your take on this? Are you in a similar spot as me, where you feel like your current success (at your “regular” job) is preventing you from succeeding as an entrepreneur?

Leave a comment below and let’s talk about it.


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15 Responses to “Is Your Current Success Preventing You From Succeeding as an Entrepreneur?”

  1. Agree with a lot of what you say and think that is why it is so important to overcome excuses to trying something entrepreneurial early on in your life, because as you get older you earn more money and have more responsibilities, making it harder to make that leap.

    However, I disagree with this quote:
    “These people won’t magically find a way to be successful in their own businesses, because starting and running a successful business typically requires a lot more work than being a low-responsibility employee.”
    It isnt necessarily hard work that separates lowly paid workers from entrepreneurs, it is the type of work they do. While many lowly paid workers are lazy, there are plenty of people working 2-3 jobs in factories or wherever for 60+ hours a week. That is hard work and MORE work than it takes to run a successful business, but it is a different kind of work.

    I think hard work is a near-requirement for entrepreneurial success, but having the right mindset to allow us to creatively determine the right kind of work is key to great success, in my opinion.
    Andy Baldacci recently posted… My First Blog Post!


    Eric G. Reply:

    Hi Andy,

    Thanks a lot for the thoughtful comment. You’re absolutely right about overcoming excuses early on, considering that’s your best opportunity to try something when you don’t have much at risk.

    And yes, I agree with your disagreement – perhaps I wasn’t being specific enough. Any old “hard work” isn’t necessarily the RIGHT type of work.

    Like you said, you can certainly be a hard worker who spends 60 hours a week digging ditches, but that doesn’t mean you have the capacity to run a business.


  2. The scenario you bring up is an interesting predicament. The person with the high-paying corporate job certainly has more to lose (both in income and social perception) by “throwing it all away” to chase some entrepreneurial dream.

    It seems the higher you climb on the corporate ladder, the scarier it is to jump.

    Thankfully I got out on the bottom rung. Had to give up a company car and the steady paycheck, but it wasn’t some crazy lucrative salary.

    Definitely a tough one the more you earn.
    Nick Loper recently posted… From Miserable and $100,000 in Debt to Self-Employed Author, Speaker, and Coach


    Eric G. Reply:

    You definitely did it right, Nick. And doing it quite well so far. :) Keep it up buddy.


  3. Nice and very informative post

    It is a interesting and important factor I don’t believe that many become entrepreneurs just by unfortunate events instead they became by some strong reason. It could be anything personal, financial or the will to earn more etc.

    It isnt essentially diligent work that divides modest paid specialists from ambitious people, it is the sort of work they do .

    Albeit being effective may be what’s keeping you down, don’t think for a minute that being unemployed is one that takes to succeed as a business visionary.

    It is truly tough being successful without hard work but only that does not take you any where.
    Sagar recently posted… How the Science of Human Emotion works in Marketing


    Eric G. Reply:

    I get what you’re saying, Sagar, and definitely agree. Unfortunate events alone do not create entrepreneurs – hard work is still a very important component.

    However, I like to think of the “unfortunate event” as more of the spark that helps the hard working person actually take action to become an entrepreneur.


  4. Yes. Absolutely.
    Mike recently posted… The LTNE Report — June 2014 (New Format!)


    Eric G. Reply:

    Makes things a lot tougher, doesn’t it? 😛


  5. You definitely need some sort of fire inside you, to actually make something substantial.

    I completely understand why it’s harder for you, considering you have a job you don’t hate, that pays well and isn’t stressful.

    You really have no reason to try harder, I guess.. Or maybe you just don’t enjoy this that much? You tell us.

    The reason I got into internet business (and soon enough, business business), was because my parents were, well, average.

    They both had 9-5 jobs they hated, both still do. Always making enough to get by in the middle class but nothing substantial. We’ve ever taken two big vacations, Egypt and Tenerife.

    I always knew that’s something I didn’t want.

    The silliest thing in the world is when you get a job you dislike even a bit. If I had a “regular job”, I’d have at least 47 more years of work ahead of me before my official retirement (which I’d probably never see, as much as I know about retirement programs).

    47 years, 9-5 of something you hate/dislike/are not in love with, for some magical reward in the end, at the “worst” part of your life?

    That’s just plain wrong.

    When my parents got divorced when I was like 15, that’s what gave me the final push.

    I wanted to do something different than what they did, I wanted to help my mom pay the bills and I already spent way too much time online.

    The answer was simple and here I am 😉
    Karl recently posted… Why I’m Moving To Montenegro For Two Months


    Eric G. Reply:

    Thanks for sharing your story, Karl – I love hearing about what motivates other people.

    I do agree with what you said about working your whole life, just to finally “enjoy” the worst part at the end of it all. Ironic and strange when you really think about it, because that’s how most people live.

    It’s the dangling carrot that is just out of reach…and when you finally catch it, you don’t have the teeth to chew it and fully enjoy it. :)


  6. Thanks for sharing informative post. It’s really useful for online readers. I have come across a lot of entrepreneurs living without personal purpose; not to talk of business purpose. They have no dream, no mission, and no target.
    I think success brings will make to walk proudly in the streets with your head up high while being happy and satisfied.
    vella di recently posted… Best Party Songs 2014 List – Top Party Music Hits – DJ Dance Party Songs


    Eric G. Reply:

    Thanks for the comment, Vella.


  7. Very Interesting & Informative Post. Many Entrepreneurs have not set their target. They work for only their personal purpose. but thanks for sharing this interesting article with us. Thank you once again!:)
    Eve Wright recently posted… Happy Friendship Day SMS for Best Friend Forever 2014


  8. Eric,
    Yes, as Tim ferries says, being “blandly comfortable” can one of the most dangerous places to be. Hard to force yourself to move on when where you are isn’t killing you, or at least no so you notice. But the work aspect is a nice addition. Ferriss downplays this important aspect in service to selling the dream. Understandable, but not realistic.

    J. F. Hussey recently posted… Goodreads Giveaway Contest Winner Announced!


    Eric G. Reply:

    To a certain extent, I agree with Ferriss. If you work a job you don’t like or isn’t rewarding, but yet you’re comfortable, it’s probably a recipe for not ever advancing to where you want to be.

    But to go along with what you said, Ferriss ignores the rewarding aspects of working a “real” job. And if the job is also very financially rewarding and you’re actually building a career (not just working “a job”), it’s a viable option.

    Then again, maybe this is a line of thinking that a true entrepreneur would never have. :)


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