Killing Them Softly: Are Sidepreneurs Bringing Decline to Corporate America?

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Happy Friday everyone! It has been another great week in the blogosphere and in the Frugal Rules home. I just want to know how ON EARTH it’s mid-September already! Don’t get me wrong, I love fall but this year is just flying by.

If you’re a reader of many personal finance blogs, you likely already know of the “hustle.” There are many other terms to describe those who hustle, such as: sidepreneurs, entrepreneurs or solepreneurs. As I was reading this article on Yahoo Finance this week it discussed the growth of sidepreneurs, especially among the millennial generation. The article went on to state that nearly half the workforce will be millennials by the year 2020 – which is only about six years away, and that they’ll likely work for at least six companies over the span of their careers. What this brought to my mind was how this will change the face of corporate America over the course of the next few decades.

Will Corporate America Weather the Sidepreneur Storm?


Corporate America has long been the backbone of our society, as it has provided many of the jobs and ingenuity in our country for years. Yes, there have been those that have gone off and done their own thing, but I think by and large so much of what has been produced as a country has gone back to the firm in our society. For many years the company, generally speaking, would provide a decent salary to the employee and often provide a good retirement plan. As I’ve shared before, that is really no longer the case and I think it could be argued on numerous levels that many larger employers simply do not care about their employees and thus it leaves things previously provided by the firm up to us as individuals.

My Dad talks from time to time about how there used to be a bond between an employer and an employee and remembers a time when the two felt a responsibility, loyalty and commitment to one another. It’s not that way anymore and it has to do with more than just companies not giving out pensions. Call me a jaded Gen-Xer if you will ;), but I think the relationship between companies and their employees has changed. It seems today that most people (employers and employees) in business feel loyalty only to themselves. As corporations pinch wages, cut jobs, slash benefits and leave things like insurance and retirement completely up to employees, workers begin to realize that they must look out for themselves. That cultural shift is to me at the heart of sidepreneurism. Workers today realize no company is going to take care of them and if they want to earn a good income and enjoy a comfortable retirement, they can’t depend on one income source from one employer to provide that for them.

Back to my point, this rise in sidepreneurs leaves me thinking how corporate America will be able to handle this shift. We’ve been seeing a growing change over the last number of years where people have become more entrepreneurial by either starting their own business or working a side gig in addition to their normal 9-5 routine. We even have a number of clients who’re in the latter camp who are growing their own business so they can eventually leave the grind and control more of their own destiny. How will the larger firms handle this and deal with the possibility of losing talent to the entrepreneurial world? I am not certain exactly how that’ll play out, but certainly a growing understanding of the need to provide appropriate benefits, rewarding top talent and allowing pathways to pursue the entrepreneurial desire that many have – especially amongst those that call themselves millennials, should be at the top of every corporation’s list.

Sidepreneurs Are Here to Stay


It could be easy to say that sidepreneurs will fall by the wayside and that it’s a passing fad – especially for someone as jaded as I am. I believe, however, that would be greatly discounting the growth and desire behind many sidepreneurs. If you read the article I cited from Yahoo Finance, you’ll notice there’s a video attached to it and it was interesting to watch as it points out the different reasons why many turn to sidepreneurship. Speaking generally, they want to be able to be a part of something that matters to them, be creative and hopefully create alternate streams of income for themselves. Looking back over the past few decades, this is not really something that was championed or even possible for many, but as the article points out, the internet has really made much of this possible.

Thinking of our own personal lives, we’ve benefitted greatly as we can do work for anyone around the world as long as we can communicate via email. This is not something that was possible when I was in high school (I know, I am THAT old as I graduated high school in the 90’s) and would’ve been much more difficult to manage just a short few years ago. Of course, the internet makes it easy for many to start a business of their own, or become sidepreneurs, but that does not mean it’s necessarily easy to do the work. That’s exactly my point though, I think we’re going to continue to see a growth in sidepreneurs as many are doing it even in light of the time it might entail.

One of the concerns I have is not only how Corporate America will respond but how this sea change will affect workers from lower socio economic backgrounds. How will people without the education, time or skills necessary to create multiple streams of income scratch out a living? And, what kind of work will be left for them to enjoy? If many of the highly skilled workers leave to start their own gigs, what kind of jobs will lower income workers have? That said, I think sidepreneurs are here to stay and I believe that they’ll only diversify in their efforts as they look for ways to grow themselves and their income – and corporate America will be forced to shift and change in order to deal with it.

Say Goodbye to Search Terms and Blog Posts


What – no blog posts or crazy search terms to share? I know, it was a tough decision, but for the sake of mainly time, I’ve decided to eliminate both from my Frugal Friday posts as I simply have not been able to keep up with it and need to devote time to other things blogging related. That said, I’ve also started to take on more freelance work, so if you’re looking for a writer on pretty much anything personal finance related, take a look at my Hire Me page and let me know!


What are your thoughts? I know many of my readers have their own side hustle, so how do you think corporate America will deal with the continued growth of sidepreneurs? Do you have anything fun planned for this weekend?


Photo courtesy of: Pamela Stocks

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I'm the founder of Frugal Rules, a Dad, husband and veteran of the financial services industry. I'm passionate about helping people learn from my mistakes so that they can enjoy the freedom that comes from living frugally. I'm also a freelance writer, and regularly contribute to GoBankingRates, Investopedia, Lending Tree and more.


  • Interesting question, John. I can see side hustle stuff trashing corporate America a bit. So many people now are doing the side hustle thing, and doing it well! I wonder what corp. America will look like in 5 years…….

    • John says:

      I don’t know that I’d say its trashing it, but definitely changing it. I agree, it’ll be very interesting to see what corporate America will look like in 5-10 years.

  • FI Pilgrim says:

    I think another growing trend these days is with young people desiring to work more for a cause than for a paycheck. Obviously both of them have to be there, but that could also be dangerous for corporations, because the most selfless employees are going to stay away from cubicle-world.

    • John says:

      I think you’re exactly right! I think that’s a huge undercurrent behind a lot of this. I know it is for us and much of why I left my job last year.

  • Hi John,
    The internet is the biggest reason for the rise of the entrepreneur. No overhead and an internet connection that you can steal from Starbucks and you’re good. You’re right as the corporation relationship has changed, if we don’t adapt we’re screwed.

  • Matt Becker says:

    I think that competition can only help in the long term. The more options people have, the more likely they are to find the best one for what they truly want. I can certainly see this as a rocky transition for corporations, but forcing them to re-think their strategies is more likely than not to make them better. I see this as a positive.

    • John says:

      I would tend to agree Matt. I think it’ll be rocky for the firms that are unwilling or unable to change with the times. I think, overall, in terms of our society that it’ll be good as it breeds more creativity and more opportunity.

  • I’ve gone back and forth about the weekly blog post mentions. Sometimes I wonder if I should do a short opinion piece instead about a current event topic. I like to give my opinion on economics but hardly ever write about it. Anyway, I think the sidepreneur revolution is empowering and I definitely am a cheerleader of it! I think corporations will actually be just fine; there are 20 people who won’t touch entrepreneurship for every 1 that will. Mainly I’m just looking at my own office and realize that there will always be plenty of corporate workers who are happy grinding the 9-5 without any additional income.

    • John says:

      I have been the same way for some time and it really does come down to time and really not being any benefit on many sides for it.

      That said, I think you do have a point. I am certain there are many who won’t go this route for the ones that do. I do think though that it will impact corporate America, to some extent. How that will be remains to be seen.

  • Seems to me the challenge corporate America will face with this issue are employees who aren’t fully engaged in their career. They have a vested interest somewhere else that detracts from the effort they put into their full time job. They show up to work tired from the long hours they put into their side work and think about that all day long instead of focusing on their job. That leads to lost productivity for the employer. I think all part-time bloggers out there can probably relate to what I’m saying.

  • This is a wonderful post and a great question. John.

    As you pointed out, I also beleive that a changing social or economic needs drive the evolution and creation of new business opportunities and ways of doing business. For example, if more people start blogging as a side business then there should be a commensurate increase in demand for computer hardware, software, internet providers, web hosting, and domain registration, etc. There both highly paid jobs and lower paid jobs in all of the businesses that I can think of. I don’t think this will change.

    Government can and does set out the ‘playing field’ for the interaction between businesses and people. While the government is often criticized for interfering in markets, they are crucial for mediating this sometimes antagonistic relationship. Individuals, companies, and governments have a strong instinct for self-preservation. I do not think that this will change either.

    • John says:

      Thanks for the kind words sir!

      You bring up a great point on what something like this could create – in terms of increased demand for other talents. I think that just calls us to be more willing to grow ourselves and learn new things so we can benefit and take advantage of opportunities.

  • Stefanie says:

    I’d love to see the continued rise of the “sidetrepreneur”. I think a lot of people, myself included, are disenchanted with the corporate world, not only because of the way they are treated, but because of corporate money and involvement in government, that has really crippled the voice and interests of the average individual person.

    • John says:

      As would I Stefanie and I think we will. I think it’s only inevitable, especially as we see the Boomer population move out of the workforce and younger generations move in and deal with that disenchantment.

  • One thing that has interested me since I first started earning online is the potential for people in lower income regions of the world to earn good money online. As long as you have a decent internet connection and a good grasp of the English language (maybe I only think that because everyone I deal with speaks English) then you can realistically run a website from anywhere in the world and earn money from it. Sorry if that’s slightly off the US corporate theme John.

    • John says:

      No apologies needed at all Adam as that is a solid point. I would agree, that if you have a good grasp of English and a good web connection then the possibilities are definitely there to make your claim.

  • Well, that’s what happens when companies stop being loyal to their employees. I think that corporate America will be fine, regardless. They’ll find a way to suck up all of the profits that they can! =/

  • Great question John. I am not sure this will really change the corporate america as we know it. Reason being (as DC pointed out), there are few people that will actually jump in as an entrepreneur. Many people are scared of it and don’t think they can do it. Yes, it is rising, but it is still a very small number compared to those that actually work for another business. Yes, small businesses runs the economy, but how that is classified can be put up for debate.

    • John says:

      Thanks! I would tend to agree, to a certain extent. I completely agree that there will be many who do not take up the side gig banner, in comparison to those that will. That said, I think it will continue to increase as the Boomers retire and the younger generations move in more. I think it’ll call firms to adapt and change, how much…is yet to be determined.

  • I think most of the people in the comments would agree that we have a bit of a biased view as we interact with entrepreneurs on a daily basis and are all pursuing our own entrepreneurial pursuits. So it may skew our vision of just how many people are taking the leap into self/side employment. That being said, I do believe more and more people are going this route and if corporate America wants to compete they have to start treating their employees better, more like humans. It seems a lot of young or tech-related companies offer incredible benefits, flexible work hours, etc. Have faith in your employees, treat them like family and it would be a lot better than it is now.

    • John says:

      I totally agree on both counts Andy. I do think more are going to go this way and the bigger firms will need to adapt to retain top talent and grow. I think many will be fine still, though those that don’t adapt may not be.

  • The internet has opened up a lot of opportunities for “sidepreneurs” that weren’t available before. There definitely will be a bit of a shift…but ultimately Corporate America has tons of money and they’re not going anywhere. Though hopefully, they’ll have to adapt to the new circumstances and maybe there will be a change for the better…that’s just a hope. And I also graduated in the 90s from high school (though the late 90s! =) I still remember being excited when I learned about the internet…and when that 56K modem came out! Very fast!

    • John says:

      It definitely has Andrew. I believe we will see a shift, which will force some in corporate America to adjust to it if they want to stay competitive. Ha ha, I remember the 56k modem, that thing seemed to move lightning fast.

  • Hey John and thanks for an informative and enlightening read!

    “…how do you think corporate America will deal with the continued growth of sidepreneurs?” – Personally, I am not a fan of corporate America or Canada so the more sidepreneurs the better as far as I’m concerned. I much prefer a grass roots economy and the more one can take back control of their lives by doing side hustles and exploring less traditional avenues of income earning, the better -but that’s just me!

    “Do you have anything fun planned for this weekend?” Always 🙂

    Take care John and thanks again for a great post. All the best.


    • John says:

      Thanks Lyle! I feel the same way, which is funny because I never would’ve though that way until we started our business. You have a good one as well.

  • I think corporate America has unwittingly created the sidepreneur phenomenon. 30 years ago it made sense to commit yourself to an employer and depend on rising income, solid benefits, and perhaps a pension. Today anyone who depends on any employer for their security is a sap, plain and simple. Only you put your family’s interests first!

    • John says:

      How do you really feel Kurt?! 😉 Seriously though, I would definitely agree on both counts. I think many in corporate America have helped bring this about and you really do need to look out for your family…because no one else will.

  • I agree that because of the lack of loyalty, the individual needs to look out for themselves. I mean we are being forced to. In my old industry (video games), it’s amazing to see how many FB postings I see of friends getting laid off time after time at these video game companies. They even have to keep moving all over the world to try and follow jobs. Crazy! I’d rather I be the one to dictate where I live (unless it’s a fabulous location and they pay for my moving costs). I don’t know how companies will deal with it, but it’s their fault I think that we are in this new type of work culture. -Tonya the Gen Xer as well. 🙂

    • John says:

      I would agree Tonya, I believe we’re being forced to and I think it’s the smart ones that are stepping out and trying to make something on their own. Those firms that can’t change and keep up with it will just be forced to in the long run or die out – of course there’s no Gen Xer attitude in that at all. 😉

  • I think that’s true in many industries, but not in others. Health care seems to get more standardized and regulated. It’s not generally something you can do online because of all the legal ramifications of not following a certain set of rules. I kind of wish it was easier for the sidepreneurs to make a dent.

    • John says:

      That’s very true Kim, I had not thought about that. There are those industries that can’t really go this way – health care being chief among them I would think.

  • I’ve discussed this a few times. I don’t think side hustles will kill corporate America. For one thing, for every hustler there are many non-huslters. Some people just don’t have it in their DNA. I think the ratios between entrepreneurs and standard employees hasn’t changed much, it is just more visible because of the internet/social media.

    Also, as people age, their desire for “easy” jobs increases. Sometimes people like not having to think much for their job. Finally, the benefits that come from working for the man are too tempting for some people. Not everyone wants to handle all of that stuff themselves, especially when it is more expensive.

    • John says:

      I don’t think it’ll kill corporate America, but it will change it and possibly bring a decline. I think those are two different things. I completely agree that there are many who will not touch becoming a sidepreneur/entrepreneur, but there are many that will. Looking back over my 15-20 years in the workforce (man that number is scary 😉 ) there has been a definite…albeit slow in the beginning shift in those looking outside of their normal 9-5 to bring in additional income and start their own thing.

      My larger point was that this growth will force, in my opinion, firms to adjust in order to meet the changes that are happening in the work force. Firms can no longer just assume that people will be happy with the same thing and want more out of their job and employer.

  • anna says:

    I think it’s great that millennials are energetic, motivated, and ambitious enough to become sidepreneurs – I think it’ll take innovative ideas to the next level, as well as encourage more outside the box thinkers. This being said, I think in order to keep up, corporate America needs to also think outside the box to retain top talent! Some TV shows or articles have millennials looking entitled or just wanting to have fun, so it’s nice that there’s articles like these that portray them as just the opposite.

    • John says:

      I could not agree more Anna, on both counts. I think this growth will only require corporate America to change and flex with the changes in order to retain that talent but also stay at the top of the game.

      I agree, there are many pieces out there that portray a gross over-generalization of millennials in that way. Sure, you might find that somewhat, but you will in almost any generation – including the jaded Gen X generation. 🙂

  • Fellow Gen X’er here. Go class of 93. I’m at the tail end of a year off from my corporate job as a Director of Finance. I am returning in less than a month, which I admit, was not the original plan. I spent countless hours debating whether I wanted to return to corporate for many of the reasons you listed here. What I’ve come to realize is, like all things, there are pros and cons to any environment and ultimately, it’s up to the individual to embrace the lifestyle they prefer and let go of the ones they don’t. Looking at the big picture, the corporate environment has given me a great many gifts that I would not be privy to had I started off my career as an entrepreneur. And vice versa, I have learned a great many things about entrepreneurship that I would never have had if I continued to blindly climb the corporate ladder. I am thankful for both opportunities. Absolutely, corporate has some growing up and adapting to do. But I don’t believe it’s going anywhere. Like all things financial, it’s the ebb and flow of a cycle. Millennials are a powerful and fierce generation. Lucky for corporations, not all of them choose the entrepreneur route. As they grow through the ranks, they will make the changes in the companies they work for and change the landscape we see today. The magic of our world today is choice. We can choose to work for a corporation, a mom and pop shop or to live the bold life of an entrepreneur. And like me, we even have the opportunity to both. It’s a beautiful thing.

    • John says:

      Hey Taynia, I am class of ’92! 🙂 All great points and I completely agree that we’re seeing much more choice today and I think the Boomer generation moving towards retirement and the younger generation pushing for more will have an impact. I don’t see corporate America going anywhere, but I do think those that do not change with the changing culture could see decline as it’ll be more difficult for them to obtain and retain top talent.

  • cashrebel says:

    That’s an interesting idea. I think even though more people will be becoming sidepreneurs, only a small fraction will be successful so it wont have a huge impact on corporate america.

    • John says:

      That’s just the thing Ross – I believe it will. We’re only going to see more sidepreneurs/entrepreneurs as we go on in the near future. I am not delude enough to think that all will be successful, but there will be those that will. That said, I believe corporate America will need to change and flex with the change and those that don’t could see decline as they could lose their ability to keep top talent.

  • Jack says:

    As the US economy falters, it becomes a matter of survival to have a side hustle.

    It’s a sad state of affairs, but people in developing countries know this by nature – there is no security other than what you make. Developed countries have grown lazy in their economic security and the innate hustle-ability of human nature has shriveled as a result. I expect to see a continued growth in people struggling to carve their own path to success through the economic jungle.

    • John says:

      That’s a solid point Jack. I would tend to agree that for many it has become a matter of survival, or at the very least, a way to have some of the things they want in life.

  • Sidehustling seems to be a big thing now not just in America but in other countries as well. A lot of people are making the switch but an awful lot also have their noses turned high up against the sidehustlers claiming it’s not a real job. I guess it really depends on a person’s perspective or standard of “work”.

    • John says:

      That’s a good point Marissa. I think it does tend to depend on your perspective. For many I have seen, they’re throwing all they can at it so I’d definitely consider it work in that case.

  • I don’t think sidepreneurs are going anywhere. I also don’t think think they’ll take down corporate America, but maybe just take some qualified individuals out of the job pool. That, combined with the mass exodus of baby boomers from the workplace make things a little uncomfortable for a couple of decades.

  • Chad says:

    I completely share your thoughts on the relationship evolution between employee and employer. I think a lot of the “side” comes as a result. People are not feeling valued or appreciated and are looking for outlets to satisfy those facets of there life. This is a trend that is here to stay.

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