Is Entrepreneurship Really Better than the 9-5?

Is Entrepreneurship Really Better than the 9-5 - picture of middle aged woman at home office

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Ever since Greg quit his job in March, we’ve been getting a lot of strange questions and looks. It seems that people thought it was perfectly normal for me to “not really have a job,” but it’s super weird for Greg to fall into that camp too. Now that we both work at home, people are racking their brains trying to figure out how we survive. A few questions I’ve gotten recently:

“How are you ever going to retire?” (This one was courtesy of a neighbor I’ve only met once.)

“Do you guys go without health insurance?” (I’ve been asked this one by almost everyone at some point.)

“What are you going to do if you lose all of your jobs?” (Huh?)

The rest of the conversations around our work situation are statements, not necessarily questions. I constantly hear things like, “Ugh, I couldn’t survive without my two weeks of paid vacation,” or “I would never give up my company 401(k) match.” And here’s my favorite, “I can’t live without a regular paycheck!” For reals?

How We Make Entrepreneurship Work

First of all, I used to feel exactly like every other person who doubts the benefits of entrepreneurship. But now that I’ve seen the light, I can’t imagine going back. For starters, the idea of having ten days of PTO literally makes me want to die. Been there, don’t want to go back. And my 401(k) match? It was great while it lasted, but I don’t miss it at all.

And that regular paycheck? Do people even know what that means? While I used to appreciate my regular, steady paycheck, I now realize that it only held me back. When I worked for someone else, they decided how much I could earn. Only now am I beginning to realize how much I was really giving up.

So yes, I totally believe that entrepreneurship is better than the 9-5. Here’s why:

Unlimited Income Potential

Three years ago, I was the Director of Family Services at a mortuary. I earned less than $40,000 per year and had almost no benefits aside from a 401(k) match. Fast forward to today – I earned $16,000 last month. This month, I am on track to earn more like $17,000. No matter how well I performed at my old job (or any other employer, for that matter), there is simply no way I could achieve the income I enjoy now in such a short length of time.

Related: How I Earn Six Figures On the Internet

I’m not the only one. In fact, a lot of people are finding that online entrepreneurship is the only way they can pull in the big bucks. My friend Michelle from Making Sense of Cents, for example, earns more than $15,000 per month all the time. Another freelancer I know, Cat from Budget Blonde, is absolutely killing it while also staying home with her one-year-old twins.

The opportunity is out there for anyone with the balls to put their worries aside and strive for success. A 9-5 job can only take you so far in terms of income. If a higher income is something you really want, it’s up to you to find a way.

Bad-ass Retirement Options

It really annoys me when people assume that self-employed individuals aren’t saving for retirement. If anything, many of us are absolutely destroying it when it comes to our retirement savings! That’s partly because we have to, but also because we have so many excellent options.

With my tax-deferred retirement plan of choice, a SEP IRA, I can stash away up to 25 percent of my income up to $53,000 per year. Compare that to the average 401(k) or 403(b), which you can only use to invest $18,000 per year as of 2015. As a self-employed person, you can also use a traditional or Roth IRA. So can everyone else, but do they? Hardly.

The bottom line: There are plenty of retirement savings vehicles aimed at making retirement affordable for entrepreneurs and self-employed individuals. And that 401K match that everyone covets is nothing compared to the power of being able to save such a large percentage of your income in a tax-advantaged account.

Unlimited Vacation

After five years at my old job, I was up to 20 days of paid-time-off, or PTO. That wasn’t bad at all, but I still had to be stingy with it. Not only do we have out-of state family that we like to see a few times a year, but our PTO days also have to serve as sick days – and our kid’s sick days. So out of four weeks paid vacation, we usually got to take two, week-long trips and a few weekend trips to see family. The rest were sick days and personal days.

That’s one thing I really like about self-employment and entrepreneurship. I don’t have to take a day off when someone is sick or if I want to enjoy a long weekend. I worked with a sick kid on the floor several days this winter, and it worked out fine. And when we take a nice vacation, I can usually “work ahead” and just answer emails while we’re gone.

Still, the best part isn’t having unlimited vacation – it’s the fact that you don’t have to ask. Working a 9-5 often means planning your vacations and entire lives around other people’s schedules, and it’s a huge relief when you are finally able to live your life on your own terms.

More Job Security, Not Less

I think it’s really weird when people assume that self-employment isn’t stable. Think about it. Having a 9-5 job usually means having one steady stream of income you can count on, while self-employment and entrepreneurship usually means having 5 or 6 income streams – and often more.

In our field, our income is earned from a handful of clients and part-time jobs. It’s pretty common for me to shuffle through a few new clients each year, but it would be very difficult for me to lose all of my clients at once!

That’s why I think self-employment is one of the most stable ways to earn a living. Sure, your income might fluctuate, but you can enjoy plenty of job security if you have a handful of diverse income streams. On the other hand, a 9-5 job is easy to lose at any time. What will you do then?

Plenty of Healthcare Options

I’m not going to lie: health care in the post-Obamacare era is hit or miss. Our healthcare options in Indiana are crazy expensive, which is why we opted to join a healthcare sharing ministry instead. However, I’ve heard people from other states say that their options are great.

Related: Why We Joined a Healthcare Sharing Ministry

Either way, if you earn less than $95,000 per year for a family of four, you could qualify for subsidies that could make health insurance affordable. Mo’ Money, Mo Problems, though. If you make more than that, prepare to bend over and grab your ankles.

The good news is, if you really need health insurance or health care, you can now get it. Thanks to the passage of the Patient Protection and Affordable Care Act, you can no longer be denied for pre-existing conditions.

Is Self-Employment Better than the 9-5 Grind?

Is entrepreneurship better than the 9-5? Now that I’ve lived through a few years of the ups and downs, I certainly think so. For me, the benefits outweigh the drawbacks – and it’s not even close. I like being able to earn as much as possible, take random Mondays off when I feel like it, and eat lunch with my daughter at school whenever I want.

I suppose it really boils down to one idea – freedom. When I worked for someone else, I had little of it. But now that I work for myself, I can live my life exactly how I want.

That comes with a lot of responsibility, of course, but I wouldn’t have it any other way. Because once you’re free, there’s no going back.

Which do you prefer? Entrepreneurship or the stability of a 9-5 job? What benefits do you appreciate from each work arrangement?

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  1. “… once you’re free, there’s no going back.” Amen to that!

    I’ve considered taking the ‘easy’ money and going back to the 9 – 5 world. I even went to a few interviews. It was at one of those interviews I walked past a bunch of cubicles, saw the forlorn looks and remembered exactly why I had to get out in the first place. An exciting job for lots of money might lure me back but it wouldn’t last long because what I truly value is freedom. So, when things aren’t running smoothly, I do my best “Braveheart” impersonation and get back to building my business.

    Your achievements continue to inspire me, Holly!

  2. Employment with a company is never guaranteed. Sometime it can come down to a decision of a single person whether you have a job or not. Entrepreneurship gives your options, and if done right can insulate you from a single point of failure.

  3. I am not cut out to be 100% self employed. I am not wired that way. I actually don’t mind my 9-5. I’m in charge of a team of 15 people (should be 18 when we finally get people through the security clearance process). I get plenty of time off, I get paid well for the actual amount of work I have to do, and my work life balance is great. My job is about as stable as they come because I work as a contractor for the government in a revenue producing area which is considered essential during shut downs.

    I am glad being self-employed works for you, but I just know myself and being 100% self employed just isn’t the way I am wired.

    1. Hey, I don’t think it’s for everyone. And if you like your job and have good benefits, that can make a world of difference.

  4. It would be impossible for me to get more job stability (tenured) and difficult to make more money, once benefits are factored in. Plus, other than teaching, which I enjoy, and the occasional meeting, I have a lot of flexibility.

    1. Flexibility is key. Perhaps that is why I feel so strongly about never working 9-5 again. At my old job, I have almost no flexibility. Something as simple as leaving work at 3 on a Friday was always impossible. I suppose that is just part of working in a service industry.

  5. “Still, the best part isn’t having unlimited vacation – it’s the fact that you don’t have to ask.” This is the best part of it in my opinion Holly. Well, the unlimited income potential is pretty darn sweet as well, but I love the fact that we can relatively do what we want when we want without having to get approval from someone who really doesn’t know us to go do what we want.

    We get a lot of the same questions and statements and think a lot of it comes from people and so often it just seems as if they don’t get it. Sure, the health insurance thing kinda sucks and we don’t get the free money in a 401(k) match, but there are too many options out there to really kill it with retirement savings that more than make up for it. I just wonder what took me so long to actually make the move. 🙂

    1. I don’t miss the 401(k) match because I can save so much more on my own. Having a group health insurance policy was nice while it lasted, but it was starting to get prohibitively expensive too. When Greg left his first mortuary job, I think we were paying something like $700 per month and still had a 5K deductible and no dental. And that’s AFTER his employer pitched in. There’s little benefit in that.

  6. In a perfect world I’d have a little bit of both!

  7. We are striving with full force to get to this point with our company. Right now I’m still working outside the home but we are making arrangements to change that within the next 13 months. This article really fired me up to keep striving for full-time entrepreneurship.

  8. Well I can definitely see the positives for both, being one of those people not earning more than I was at my full time job. I think it you got the system worked, like you do, there isn’t even an comparison and why would you ever want to go back! But sometimes I definitely miss the security of a full time job! 🙂

    1. I hear ya, although I don’t miss my old job at all. I miss the people, but not the drive and the hours and the stress.

  9. I still fall into the trap that a 9-5 job is secure employment when the reality is that you aren’t guaranteed a job tomorrow. My biggest scare for going down the entrepreneurship route is the insurance! Many people in private practice in my field of work have mentioned monthly insurance rates of $500-700/month. Yikes, that sure seems like a lot of money!

    It was so good to read your thoughts and viewpoints on this topic! You continue to inspire me to move that direction!


    1. Yep, the whole insurance situation can suck. Hopefully you don’t live in Indiana and/or you qualify for subsidies that actually make it affordable.

  10. My situation is a little different because I still do some 9-5 days, but I get to choose how many and can bank a bunch of days so I can take several weeks at a time off. I was never able to take more than a week in my past life. I think if I ever had the nerve to walk away from optometry, my biggest issue would be not working all the time. I have a gazillionith of the freelance work you have and I still find myself working every evening and part of the weekends. I guess the good thing is that I can choose the times when I work. I’m getting ready to go to an assembly program at school in a little while and I would have never been able to do that working full time.

    1. That sounds like a good compromise. Taking several weeks off at a time sounds awesome! I’m self-employed and can’t really even do that.

  11. HELL YES I prefer entrepreneurship.

    Although I’m not making close to what I was at my full-time job (because I’m working extremely part-time hours right now to focus on being a Mom), I know that my potential is unlimited doing what I do. I find way more security in creating my own money rather than counting on a company to not lay me off.

    And when the time comes to have all my kids in school full-time, I can’t wait to grow my business and see how far I can take it.

  12. I really like my corporate job. Maybe I could make more self-employed if I knew how to find clients in my field. But I make in the mid $100k range with cheap healthcare, $42k going into a 401(k) between me and my employer, an ESPP (employee stock purchase plan), three weeks of vacation, a good separate number of sick days, and smart people to work with, all with flex time, paid maternity leave, and working ~40 hours a week. I don’t see much reason to look for self employment when I like what I do!

  13. I definitely see some of the pros especially the flexibility and the part where your success results from your hard-work. I work in government so there sometimes is not much incentive to work harder or more efficiently. Pay is based on seniority more or less. One thing holding me back from entrepreneurship (besides lack of a business) is that my job also has excellent benefits and pretty good pay. The pension is the one benefit which is like a golden handcuff.

    1. That’s how my old job was. It wasn’t seniority-based, but everyone basically got the same raise no matter what. That wasn’t very motivating for me.

  14. This post is exactly why I’m working toward entrepreneurship — freedom. It certainly depends on the person, but I love it and yearn for it. I’m looking forward to the day when it’s a full time reality.

  15. Sounds ideal to me! I really look forward to having that freedom to control my own schedule in a few years when we’re on the homestead. I think it’s awesome you two have made this dream a reality–it sounds like you have such a great work/life balance. And, you make such a great point about the potential to earn more–you’re not hemmed in by an organization’s salary bands!

  16. I worked for home for years with my previous employer and it was awesome because I loved the job and flexibility. After the company closed (owners retired) I took a normal 9-5 job and have been schlepping it into the office for a year now. I hate it! I am spinning my wheels trying to figure out how to either A- become location independent for another employer or B-make it on my own. B is a little out of the question for now, but a goal I hope to see in the future. Reading your post is really inspiring and great motivation, thank you!

    1. Location independence is key for me. I would have been a lot happier working for someone else if I could have done it at home! Being tied down and staring at the clock all day is what killed me.

  17. Thank you so much for the mention! Outsiders just don’t “get it” — The truth is that entrepreneurship is a huge risk (at first) and most people just don’t have the guts to do it.

  18. I think this really comes down to what kind of entrepreneur we are talking about. I think there is a huge difference between being a contract worker who has a bunch of work contracts versus building a business where you as the owner can eventually remove yourself from day-to-day operations. Owning a business that you can eventually sell your equity stake in for a large lump sum is definitely more ideal than working a 9-5 job. But I think if we are talking contract work versus 9-5, it depends on the 9-5 (and the contract work). I’d much rather be working my 9-5 job than contract work, but I also see the huge potential benefit of selling a business for a lump sum, which was my original draw to entrepreneurship.

    1. I agree with your sentiment on contract work vs. self-employment. They aren’t necessarily the same thing. We do both- own businesses and contract work – and I see value in both, but prefer the business aspect of things. Then again, I’m probably most comfortable with a combination. Our businesses bring in a decent income but not as much as I prefer to make.

  19. I agree that you have found a great life work balance. It isn’t for everyone but you are proof it can be for those wanting something better.
    Personally,I admire you for being able to put as much as you do into your site. For me though,I like my current job finally after years of unhappy ones. Great benefits(considering I’m only part time,yeah!) and helping others in my job is my satisfaction. But would love some of the income versus flexibility benefits you mention.

    1. Hey, I would love a part-time job with benefits! That would make it easy to do a little bit of both.

  20. Thanks for pointing out the SEP IRA. My jaw hit the floor the first time I heard about that little gem.

    While a 9-5 job can be ideal for some, especially with good pay doing a job you love, it\’s hard to argue the freedom you get from going your own way.

    At some point I\’ll need to make that transition, but for now, the stability and predictable hours of a 9-5 gig fit my needs.

  21. The freedom alone makes it better. I was recently let go from my “real job” in effect because I was too focused on building my own business. Best thing that ever happened to me. I never feel like I’m working, I’m following my passion. Great write-up.

  22. Because my business is more of a 9-5 operation, I have never had people make similar comments to me. Most either run away as fast as they can when they hear I’m a financial advisor or want free advice. Or argue. Some really want to do that too. 🙂 I definitely prefer entrepreneurship but I have worked with entrepreneurs who are truly better suited to be employees and vice versa. I think there is still an old belief that entrepreneurs and consultants and freelance are code words for unemployed, so people question how it can work and most have limited experience seeing it work well. Congrats to you and Greg for making it work exceptionally well for your family!

  23. My grandpa (a serial entrepreneur) always said that the best part of owning a business is that you’ll never be unemployed, but the worst part is that you might not have any money. All told, he was very successful, financially and otherwise.

  24. I have the best of both worlds at the moment with my current traditionalish job: I have an incredible amount of autonomy and freedom to direct my work and my schedule. My schedule is about as flexible as it gets with the minor exception of a couple meetings every couple of weeks. And I have a steady really decent paycheck no matter how much I work. Or how little, depending on the day.

    BUT – there isn’t going to be room to increase my income level for a while so that’s the drawback of this security. It’s good for now but I’m already looking into the various entrepreneurial things I could branch out into because like any job, this won’t last forever! It’s always a bit of a kick in the pants seeing your numbers or Michelle’s or Cat’s: It can be done if I find the right combination of things to do!

  25. I myself have contemplated an entrepreneurial career, but do not see myself pursuing it for some time. Once I have developed the necessary expertise and network, then it would be more appealing. So much time is often put into establishing oneself and building the business and I am not quite ready for it. I currently work for a start-up organization, so I get some of the perks of the entrepreneurial spirit, but still the “safety net” of a more established 9-5 job.

  26. I could not agree more. I was recently laid off from a fairly glamorous publishing job in about the same amount of time it takes to eat a taco. My “stable” job just wasn’t and all your points above drive that home big time.

  27. I’ve been an entrepreneur for over 13 years. At this point I’m unemployable as most companies can’t wrap their head around the concept either. I’d never go back to the grind of 9-5 but with that being said, it’s not for everyone. It has it’s up and downs but for me it’s been mostly up!

  28. Being an entrepreneur is honestly the hardest thing I’ve done. Starting LendEDU was a difficult journey, and committing to work on the business full-time is a tough pill to swallow. Luckily we went through a startup accelerator, and we were able to take the plunge fairly quickly. That being said, the hardest part of being an entrepreneur is the fact the your day never ends. The 9-5 isn’t existent, but the 7-11 is! If you get a call at 11pm you need to answer it! Tough life, the ups and downs can really beat you down sometimes.

  29. I can’t juggle a ton of things at once. (I’ve got enough going with our health problems and managing our finances.) So a 9-5 suits me just fine. I don’t know that I could deal with the uncertainty — at least in the beginning — about how much money would come in.

    That said, I think people misunderstand “self-employed.” They think of the more traditional situation of someone setting up a single business or just freelance writing or… whatever. If people understood that you had multiple income streams, they wouldn’t ask so many dumb questions.

  30. I think self employment is the best way to go if you have the brain to go with it. You have to have a tolerance for risk and depending on yourself. I was an employee for 31 years before retiring early and during that time I also owned to small businesses at some points. I loved the time I worked in my businesses much more the my main career. I have worked along side highly technical employees as a consultant/contractor (much higher pay/no benefits) and prefer that to full time employment too.

  31. My husband is self-employed, and one thing he wishes he could do is turn it off every once in a while. There are times when he works 16-hour days for weeks on end. When business is more steady and less crazy, he has many of the advantages you speak of. And they sure do sound like great advantages! Congratulations on making it work : )

  32. Don\’t be surprised if I write a very similar post to this one in the future. I am ALREADY seeing the truth of every single thing that you\’ve mentioned in your post. It has been a little rough in the beginning (nothing comes easily) but I\’m already on track to make well over what I used to earn at my job previous job. I worked for 10 years (in education) and I had around 5 weeks of vacation time. Big deal. I also had chronic exhaustion, chronic migraines, depression, anxiety, weight gain, and was painfully single. I\’m still single…but it\’s not so painful anymore LOL! I was working 50+ hours a week but my money didn\’t scale up in the way that it can now. I have no problem working hard. But it was really pissing me off that I wasn\’t financially benefiting from my hard work. Love this post.

  33. Hi Holly

    First time at your site here to say hello from the east.

    Nice post here on the entrepreneurship versus corporate job.

    The only biggest difference I would say is the timing of those cashflow. In corporate job, you get those fixed income every month but not necessarily so with entrepreneurship. BUt once you get things up nice and done, it’ll be way over the moon as you said up there.

  34. Tony @ Inequality Today says:

    Definitely entrepreneurship. As an entrepreneur at least I know that I’m in control of my own destiny. If I failed, it’s because of my own shortcomings. It’s not because the CEO lied about the company’s finances or because a political power play cut 15% of the company’s staff. I hate the feeling of having my own life controlled by bosses.

  35. Right now I prefer the stability of a 9-5 but have a tremendous amount of respect for anyone who ventures out on their own. $15k a month is crazy high. And I think it\’s all in the perspective, for some it\’s the fear of the unknown but others see it as limitless opportunity

  36. Hi Holly, it really depends on situation and preferences. But, I think entrepreneurship sounds better than 9-5 as we have control over our time; however, there are down sides because we do it our way and it requires planning, commitment and truly hard work. Being self-employed is a matter of choice.

  37. Entrepreneurship is not for everyone, but I am a huge fan of it for a number of the reasons you mentioned. I worked for many years for an investment bank and continued to improve my skills, my work and my business, yet my pay seemed to have plateaued. As an entrepreneur, there is not cap to how much I make, just how much I am willing to work. Also, when I left my former company, a fellow entrepreneur said that you are going from one boss (i.e. the firm) to dozens of bosses which gives you way more job security as you don’t have to worry about the whim of just one boss making or breaking you, and I feel like that now. My business is spread out to a number of bosses that I know I would be comfortable financially if something were to happen to any of them.

  38. Great post. I was talking to someone over the weekend about the perception of self-employment not having as much job security as a permanent role and whilst in some cases it can be true it’s also a fact that in the last 5-7 years redundancy has been common place in so many companies which makes you wonder just how more secure a “permanent” role is.

    It is about freedom, it’s also about being able to be brave and go and grab the life you want!


  39. I’m certainly not saying it’s for everyone but I am fully in favour of the entrepreneurial stream. My husband was recently laid off from his “steady paycheck” job and my hours were cut by 30% at my “steady paycheck” job so there’s no security even with ol’ faithful 9 to 5. What’s saving us is our three other streams of income from side businesses.

    For me, I don’t mind my day job but I’ll never allow a day job to dictate what I’m capable of earning, saving, and spending. Thanks for the post, it made my day!

  40. The loss of a steady paycheck and all those other reasons are more of an excuse for people to justify why they wouldn’t go out on their own. I think those are great problems to have! When you get to be your own boss, you get to make up the retirement/health care/vacation rules! It may seem daunting, but I’m hoping that one day I can become self-employed.

  41. I think there is no doubt that entrepreneurship is far better than daily 9-5 job, if the plans worked. Besides money its give a huge satisfaction of doing something own and the flexibility provided to family, which is simply priceless.

  42. Just found your site and I am now one of your biggest fans! When my children were young I worked from home doing whatever I could to earn money. When my daughter went to college and I was a single mom, I had to go back to a 9 to 5 job and hated every second of it. We had to pinch in on our computer how degrading! I am happy to say I am working from home again as a freelance writer and an eBay seller and loving every second I get to spend at home with my husband and my dog!

  43. Astha jayakody says:

    Great article Holly!
    It was by luck I found this site.This article inspired me to try out entrepreneurship without giving up my regular job, as i am in love with my regular job (army). Previously, I tried out entrepreneurship, but received a lot of backlash from the family that I had to temporarily halt my plans. (That is what happens when you, your wife, your parents, your uncles, your aunts, your cousins, your grandparents, great-grandparents, etc… are all commissioned army or navy officers ). Basically everyone around me is into this “honor” concept, and their only true living pathway is government or military service. Anyways, I’ve been a bit rebellious since youth and am looking forward to give my colleagues and family a shocker by becoming a part-time entrepreneur. I would appreciate it if you have any tips to balance a full time job and a small business.

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