Taking The Plunge is Not Just For Polar Bears – Part 1

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Taking the Plunge

Today’s post is the first entry in my little serial on self-employment. Now, this isn’t the Pickwick Papers and I’m not Charles Dickens, but I am making Frugal Rules the publishing house for my story about taking the plunge into being my own boss, running my own business, and diving into the deep end of self-employment as a husband and father of three little ones. I hope you enjoy this post and keep your eyes open for future installments as I describe my journey into the strange, scary, and scintillating world of self employment.

Living in the Midwest (Omaha, Nebraska to be exact) I’ve seen an event called the Polar Bear Plunge. For those of you not versed in what the Polar Bear Plunge is, it’s a day in which people willingly throw themselves into the nearest body of water during the cold, barren winter.

Call me crazy, but I’ve always wanted to try this it as I love cold weather but haven’t worked up the courage to do it topless in front of a crowd yet. To the unsuspecting onlooker it might seem crazy or even stupid, but I imagine there’s quite a rush involved in taking the plunge. Though I have not taken the real Polar Bear Plunge, I have recently dove head-first into self-employment and it so far has been worth the plunge.

Why I Took the Plunge 


Roughly five years ago I graduated with an MBA in Finance and was told by many to expect multiple, attractive job offers. Over the past five years I’ve held two separate jobs in the investment industry, neither of which got me anywhere or allowed me to use my education. I’ve been on so many interviews that I’d consider myself a professional interviewer. Numerous times I’d come in second and be told that I just didn’t have the experience but that I was a great candidate.

Fast forward five years and I am still stuck in the same dead end job sitting next to a guy who groomed himself at his desk. I was miserable and simply looking for someone to give me a chance to prove what I could do. This turned into nightly discussions with my wife about giving myself a chance – or, ‘taking the plunge.’

While all of this was going on, my wife started her own business as a freelance copywriter that I was starting to help out with as well. She had been in the advertising industry for roughly eight years writing website content, direct mail letters, print, radio and TV ads, marketing materials and much more for small businesses, nonprofits and even a handful of Fortune 500 companies as well as national brands. Even better, we had grown a nice sized business doing it.

My wife was having to turn business down because her schedule didn’t allow enough flexibility to care for our three children and take on additional work. We started looking at the numbers at how much she was able to make versus how much I could make and it was becoming clear that a change was needed. After months of discussion and analysis, we decided that the best way for me and us as a family to get ahead financially was me taking the plunge into running our own business full-time. I became a part-time writer, part-time manager, part-time administrator and part-time blogger and for the most part, I am loving every minute of it.

Taking the Plunge is Not For Everyone


I finally pulled the trigger six months ago and quit my day job to devote time fully to running our business. I will be the first to admit that taking the plunge is not for everyone. If you have visions of sleeping in until noon every day and playing video games, then you’re wrong. Being your own boss requires discipline and a vision for where you want to go as well as where you want to take your business.

This means that you have to create your own structure and become a pro at time management. There is no one around to tell you that you have to work at a certain time and take lunch at a certain time. If you do best in a more structured environment, then taking the plunge is probably not for you. But if you’re self-disciplined and yearn for more opportunities, responsibility, and autonomy than your current profession affords, then leave your options open.

Next time, I’ll continue my journey by discussing what I’ve found to be some of the rewards and risks of taking the plunge into self-employment.

Today I want to know if you have you taken the plunge and become your own boss? If so, how is it working for you? What things would you have done differently?



Photo courtesy of: Tim Barrett

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John is the founder of Frugal Rules, a dad, husband and veteran of the financial services industry whose writing has been featured in Forbes, CNBC, Yahoo Finance and more.

Passionate about helping people learn from his mistakes, John shares financial tools and tips to help you enjoy the freedom that comes from living frugally. One of his favorite tools is Personal Capital , which he used to plan for retirement and keep track of his finances in less than 15 minutes each month.

Another one of John's passions is helping people save $80 per month by axing their expensive cable subscriptions and replacing them with more affordable ones, like Hulu with Live TV.

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  • Thad says:

    Great story. I think you demonstrate why there are no easy roads to success. Not that you thought the MBA would be that (that I can tell), but there are many times that things don’t work out the way we thought they would. Reassessing and adjusting is needed, and just what you did.

    • John says:

      Thanks Thad. No, there’s really no such thing as an easy road. I think anything worth while does have a cost and can be quite challenging at times. Looking back, many of the things I learned with my MBA are things I am able to apply to our business today.

  • Justin@TheFrugalPath says:

    I’ve been contemplating this for some time now. Finally after a few years I’ve started the planning process, but it will be some time before I actually take the plunge.
    It must be a good feeling though to know that you’re making money for yourselves and not just some guy at the top. Good luck with your business ventures John.

    • John says:

      It is quite satisfying Justin, especially when we can see growth and know that our hard work is paying off. That’s one thing I can’t stress enough…taking your time before you make the decision. There’s so much more than I ever thought in regards to running your own business full time.

  • Mrs. Pop @ Planting Our Pennies says:

    I’m eagerly awaiting more of this story… and the numbers junkie in me would also love to hear how you’ve dealt with things like more irregular income, health care expenses, etc. =)

    • John says:

      Glad to hear Mrs. Pop! I’ve already written a post for Kim over at Eyes On the Dollar about budgeting, but plan on doing one myself as well in this series. There’s quite a few things I’ll be writing about, so rest assured I’ll be probably covering all I can think of.

  • Pauline says:

    I like how the risk was controlled because your wife left her job still having you at a full time job, and then when her income was quite stable you left yours. With a full family it would have been a great risk to start both at the same time with no guaranteed income. I left my job 3 years ago and I still suck at time management. Because no one depends on me, I just do as I please and you can find me working at 11pm or sleeping until 10am, I keep saying I should be more organized but kind of work poorly within a structure. What I would have done differently is network more before I left my job. My favorite clients still send me some work from time to time but the others are long forgotten.

    • John says:

      Yes, the risk was a bit mitigated Pauline. Though it did not “feel” like it at the time. Time management is huge, without it we’d be nowhere. You bring up a great point of networking, you always have to be doing that when you run your own business.

  • Deacon @ Well Kept Wallet says:

    That is awesome that you “took the plunge”. I bet time management is the toughest part. Look forward to hearing more!

  • Mandy @MoneyMasterMom says:

    We have a polar bear dip January first at the beach in Port Dover. I’m with you, I really want to try it once. Although I won’t do it topless. That seems inappropriate ๐Ÿ™‚

  • DC @ Young Adult Money says:

    Thanks so much for sharing your story (and I’m hoping for many more posts on this topic!). I am considering an MBA in Finance, so I will definitely take your experience into consideration. My current job at a Fortune 20 company is nice – the experience, the benefits, etc. are all really good and I am learning a lot. I think the biggest thing for me is that 1) My pay is essentially capped and 2) There may come a point where I am simply not learning enough to keep me engaged. I also am very interested in starting my own business where I have to make every hour count and not just work 40+ hours and try to work just to fill the hours because the 40 hour work week is such an institution in corporate America. Great post!

    • John says:

      Not a problem DC! There will be more, one on Wednesday to be exact. ๐Ÿ™‚ Like I said in response to another comment the MBA was not what I was expecting it to be, but I am now calling back on things I learned during my time…plus I found something I love. The big thing for me in regards to my previous jobs was that I was not being mentally challenged which made it very difficult for me. I thrive on being challenged and it was not there and thus I was miserable. Add that to the possible uncapped income and the ability to better our situation and it was a no brainer.

  • Kim@Eyesonthedollar says:

    I’ll pass on the polar bear dip, but I did decide to buy a practice ten years ago vs being an employee. I know how tough the thought process is. So many people come out of school and thing the perfect job is right there for the picking, but in reality, we have to make our own situations sometimes. I love that you took the plunge!

    • John says:

      It is a very tough thought process, especially when you have a family to be concerned about. I agree that we do need to make our own circumstances sometimes. Sure, we might go down in flames…but I’d much rather have taken the calculated risk than not.

  • Jason says:

    Wow…for some reason I didn’t realize that you’d only taken the plunge 6 months ago. I thought you’d be doing it for at least a few years. Craziness!

    Well, I’m certainly glad to hear that things are working out. I’ll also echo the fact that being your own boss is not for everyone. Sure, it’s a lot of fun when you’re making money and things go well; however, when things take a turn for the worse, it’s not fun trying to figure out where income is going to come from.

    • John says:

      Yea, officially only six months for me. Though, I have been helping my wife out with the business to a certain extent ever since she started it.

      I agree, being your own boss is not for everyone. I am actually covering that on Wednesday. It sounds great in theory, but the rub is that it’s ALL up to you. I enjoy it and love that we actually get to see the outcome of our hard work.

  • Budget & the Beach says:

    I had a different experience in that the plunge was taken for me. I was laid off and thrown into the fire. My advice to anyone would be to live “like” a freelancer before you leave your full time job, ie, try to budget your money from a one month salary and try to make that last for 2 months or so. Realty shock! But that’s what it is or can be like. Better to be prepared! But now that I’ve been doing this for 4 ish years, I’ve leaned so much (usually the hard way) and don’t regret the experience at all!

    • John says:

      It can be MUCH different if your laid off Tonya! I am thankful that we could take a measured risk. I would agree that living like a freelancer is a great way to get your feet wet. That can help you possibly build a small but consistent client base in which you rely on.

  • Grayson @ Debt Roundup says:

    When I was running my online ecommerce store, I was about to take the plunge. I was making enough money, but then it finally hit me that I no longer had passion for the business. I didn’t want to take the plunge into something that I would hate doing. Luckily, I have a job that I love and it keeps my mind busy with new tasks.

    • John says:

      Great point Grayson! I am actually planning writing a post on that myself. I agree that if you don’t enjoy what you’re doing and have no passion for it that it will get old VERY quickly.

  • CF says:

    Can’t wait to read the rest! While I enjoy making side income here and there, I’ve never had too much of an interest in being my own boss – too much pressure and not enough motivation on my part!

    • John says:

      Thanks CF! Motivation is huge. I thought that I would never be motivated enough to be my own boss, but a funny thing happens when your kids eating really depends on you…you get motivated pretty quick! ๐Ÿ™‚

  • Mackenzie says:

    I am eagerly awaiting more of your story!!! That’s great that you were able to incorporate working and balancing your family. That is inspiring to me ๐Ÿ™‚

  • Retire By 40 says:

    I retired from my career about 6 months ago too. I’m definitely not waking up at noon because I’m a stay at home dad blogger. Our little guy keeps me superbusy and I love it. Being self employed is so much more fulfilling than working for a corporation. I’m making much less, but I’m prepared so I can give it 5 years or so.

    • John says:

      Awesome for you! I am usually up by 5:00 myself, 5:30 if I am sleeping in. I agree that it’s much more fulfilling than being in a Corporate gig, I live that I get to see the results of what we’re doing.

  • My Money Design says:

    Quite inspiring! I’ll be interested to hear how the rest of it goes and how you guys sustain this business.

    • John says:

      Thanks MMD! We’re excited about it and excited to see where it goes. Our vision is to eventually start our own ad agency.

  • Veronica @ Pelican on Money says:

    Everything you say here rings a bell ๐Ÿ™‚ I took “the plunge” several years ago and for 2 years did fairly well. At first, it was similar to living a nightmare. You never know what’s going to happen, whether you’ll make money tomorrow, if you’ll have enough to pay all the bills etc etc… It’s a scary feeling! But once you get going and self-confidence grows, it’s a feeling I seek to relive again. You’re right about discipline – I think it’s one of the hardest challenges for anyone thinking about self-employment. It sounds peachy, but when it comes down to motivating yourself it’s HARD!!! There were days when I did absolutely nothing besides getting out of bed to go to the bathroom and eat some food (then back to bed). Those days I felt like a worthless human being and wondered what the heck I’m doing with my life. Then on the other spectrum were days where I’d do really well and have time left over to do whatever the heck I wanted to do. Those days were awesome. You see people going to work and realize you’re not part of the same rat race anymore. There’s so much to be said about this that I’ll probably write a post on it. I’d like to see more of your self-employment thoughts though, it’s interesting to see how others are doing it and what kind of challenges / emotions they cope with in the process.

    • John says:

      I can relate to some of those feelings Veronica. That discipline can be a beast sometimes and really can be hard to motivate yourself if you’re seeing no fruits from your labor. That said, having three little ones to feed can be a pretty good motivator. ๐Ÿ™‚ Those days where you have wild swings from a lot to nothing can be difficult emotionally and financially. I am just so thankful that we already had a solid budgetary mindset prior to taking the leap.

      As an fyi, this is going to be an ongoing series (I have a post going live on Wednesday as a matter of fact) that I’ll be doing. I’ll be covering some more of the challenges/rewards and more about what we do. I’ll also be covering things like insurance, retirement, etc that you have to look at when self-employed.

  • Matthew Allen says:

    This should be quite the interesting series. Taking the plunge isn’t even close to being on my radar, but I love reading about others who are able to. Looking forward to more, and hoping to see some numbers..?

    • John says:

      That’s what I am hoping Matt. It never used to be on my radar either, but when you look at the numbers it starts to make more and more sense. I’ll share generalities, but not specific numbers. Suffice it to say, we’re supporting a family of five off of it.

  • Johnny @ Our Freaking Budget says:

    “If you have visions of sleeping in until noon every day and playing video games, then youโ€™re wrong. ”

    Welp, there goes that dream. ๐Ÿ™‚ As a fellow copywriter currently working for the man at an ad agency, I’m excited to hear your experiences in self-employment. It would require a pretty solid nudge off the cliff for me to take the plunge, but I’d be freaking fantastic to do it one day.

    Look forward to following this series.

    • John says:

      Lol! ๐Ÿ˜‰ My wife had been a copywriter for an insurance company for about six years and there’s only so much you can do in that role and started to freelance with some ad agencies around the area. That’s what started it all. It is pretty fantastic, especially when you see your work on a national campaign…pretty awesome indeed.

  • K.K. @ Living Debt Free Rocks! says:

    Great idea on doing a series concerning self-employment! I became self-employed earlier this year in large part due to personal and relocation reasons – I had written the post Life Is What You Make Of It a few weeks ago that talks about this transition. I’ll admit at first I was anxious about losing the matching RRSP contribution, affordable health premiums and other perks that came with being an employee for a large corp. My husband has been self-employed for over 15 years and he was helpful and reassuring that we had our ducks in the right row and to not doubt myself or my decision. Self-employment definitely has its challenges and it is not for all but I am very organized and structured so I manage to get a lot done each day. Being able to work from virtually anywhere in the world at this point is priceless to me. The quality of my life has increased since becoming self-employed.

    • John says:

      Glad to hear you’re on the journey as well K.K. I agree that it’s not for everyone and I too was concerned about losing all of the benefits. But, at the end of the day, this is so much more fulfilling than any of my previous jobs. Plus, the quality of life definitely has improved for me as well.

  • Jon @ Grown Up and Stuff says:

    My girlfriend and I have always said that we’d be fantastic in business together, so we probably will end up working together at some point. But right now we’re still fairly fresh out of University and so we’re still trying to get our heads around the working world.

    We could just take the plunge, but we would need some sort of backup first! I’m too much of a scaredy cat haha!

    • John says:

      Having that ability to work well together really is vital. I know for many they could not do it, but thankfully my wife and I balance each other fairly well.

      I would definitely say having a financial back up is of immense importance when you go into self-employment. The swings can be very stark and you need to have a solid base backing you up.

  • Tackling Our Debt says:

    Congrats on working together with your wife to build a successful home based business. I think it is wonderful when couples can work together and stay home with their children at the same time.

    • John says:

      Thanks Sicorra! My wife and I will be the first to say that it’s not for everyone. It’s definitely a huge bonus for us to be able to stay at home with the kids and be a part of their day to day lives.

  • Roger @ The Chicago Financial Planner says:

    Great post, I can totally relate having done this in the mid 90s. Oddly enough I have an undergrad finance degree and an MBA and everyday of my work life (both employed and self-employed) have been spent in the finance arena in one form or another. In my case moving to self-employment has allowed me to pursue what I really enjoy, investments and financial planning. Corporate finance was just not my cup of tea. In our case my wife went back to work about 9 years ago and she supplies our family benefits which has be key for us. The additional income with 2 in college has also been a real boost. Life is far too short to get up and go to work at something you hate. Kudos to you for taking the plunge.

    By the way the polar bear plunge was something we would watch on New Year’s Day back when I lived a block from Lake Michigan back in Milwaukee.

    • John says:

      Thanks Roger! That’s great your was able to go back to work and cover for the benefits and I can imagine the extra income is nice with having kids in college. I agree that life is far too short to go to a job that makes you miserable and starts to impact your health negatively.

      I’ve been wanting to do the real plunge for several years, who knows…it might be in my future.

  • Canadianbudgetbinder says:

    Thanks for sharing this John. Congrats on quitting the day job to take on this business venture. I think if you have the passion and the desire to succeed you will. Like you said you have your MBA and you jokingly say you are a professional interviewee so taking the next step and not waiting around for someone to call is awesome. We don’t get anywhere in life without some hard work and where better than in the comfort of your own home!!! Cheers John… looking forward to part..2 Mr.CBB

    • John says:

      No problem Mr. CBB! I would definitely agree that anything worthwhile does require hard work and it can be so rewarding to see something you’ve done take off.

  • Daisy @ Money Smart Guides says:

    Congrats on doing something that you believe is right for you. That’s great. Especially since you weren’t enjoying your day job! Being self employed is tough and not glamorous at all like many people want to make it out to be. But I am sure it’s rewarding being able to make money for yourself, by yourself.

    • John says:

      Thanks! It can be tough and is not for everyone. It definitely is rewarding and it’s a great feeling to be able to be successful and know what you’re doing is benefitting you and not some massive corporation.

  • Michelle @ See Debt Run says:

    Great story, John. Now I’m looking forward to reading the rest! I think it’s very brave, but having a clear plan and a level head like you do lessens the risk and raises the potential. Also, this was a business that you were already able to see the start before committing to, as your wife had already been hard at work! Wishing you and your wife much success to come!

    • John says:

      Thanks Michelle! I would agree that having a clear plan is a must have, otherwise you can just tend to be aimless. I do owe A LOT to my wife and she is really the engine behind a lot of the success.

  • Money Bulldog says:

    This is a great post John!

    I spent about 6 months of my working life employed and hated every minute of it. I don’t mind the structure of working life and the regular income, but I seem to have an inbuilt desire to make my own money and build something from nothing.

    It’s difficult starting a business but it’s also exciting and I think it’s that excitement that drives an entrepreneur. Now I just need to take the plunge into blogging full time!

    Keep it up mate, I’m heading to the next post in this series now!

    • John says:

      Thanks so much! I don’t mind the structure either, but what I was missing was the variety and being able to see an outcome that I helped bring about. Getting lost in the corporate world can be mind numbingly tedious and monotonous. It’s hard to see the outcome of your hard work and in the end you’re doing it to benefit the firm and not yourself.

      It is difficult to do, but anything worth while will be difficult in my opinion and the great thing is that the income is unlimited.

  • Barbara Friedberg says:

    Good luck and congratulations. Is this website your business and do you have other ventures as well? How are you generating income?

    • John says:

      Thanks Barb! No, this blog is only a side thing for me. What we do for our business is to work with companies from non-profits to Fortune 500 companies form their marketing campaigns. We get to help many from the ground up determine their advertising voice and what they want to communicate. Ultimately our vision is to start our own ad agency.

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