Taking the Plunge: What the Hell Have I Done?!

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Taking the Plunge

Do you ever have those times where you wonder WHAT on earth you were thinking when you made a certain decision? I hate times like that as it makes me question whether or not I acted too rashly or if I made an absolutely idiotic decision. This was the place I found myself in this past summer as the responsibilities of running our own business came home to roost. We had taken several months to seriously contemplate and run the numbers to see if taking the plunge was right for us or not. We made the decision for me to quit my day job in mid-May and things were going great for the first month or so and then it came to what seemed to be a screeching halt. Questions raced through my mind and I seriously wondered if I had completely misled myself. I share what I do not as a means to be a motivational speaker, but to share some of the things you experience when you’ve decided to take a huge step like this.

My Dream or a Desk Job?

To take a step back in the discussion, there was a financial company I had been trying to get into for several years here in my hometown. I had interviewed there four or five times over the course of maybe 18 months and each time I came in second. My last interview with them was for an opening for an analytical role I was interested in.  As with all my previous interview experiences, I lost out to an internal candidate. This was frustrating, but I did respect their philosophy of promoting from within…much of why I wanted to go there. Well, as we were in our decision making process I had one final interview there. Things went well but I did not hear back from them for several weeks. Literally the day after we made our decision I got the call that I had been offered the job. My thoughts were WTF, where was this job offer a year ago? So, in the span of 24 hours we dealt with what should I do? Should I give up on our dream for this job or was I just being silly for questioning giving up on our dream. The sad fact of this job was that it was at the same level I was at in my previous company and who could say where I would go over the course of time. The job meant nothing in terms of a pay raise which was a disappointment. After a thoughtful night of discussing it with Mrs. Frugal Rules we decided to stay the course as it still did not change the fact that we had a vision and wanted more in life than a desk job.

Where the Hell is the Work?

The first month or so we were killing it, or so we thought. Business was coming in and one of our clients had signed us for a larger retainer. Things were going great and then, all of a sudden, there was no work. I mean NOTHING. We had been going to networking events, following up with past clients, meeting with new potential clients and absolutely nothing came in. As someone who tends to not doubt himself, this was a bit jarring to say the least. We questioned if we were doing things wrong or if we had made an absolutely boneheaded decision. I even questioned whether or not I should call that company back seeing if they had filled the job or not. We also learned over this time that people are liars and that work we had counted on was nowhere to be found. I know it’s crazy, but you need work to pay the bills and we weren’t getting any work. We ended up having a couple of months where we were barely scraping by. It’s amazing how quickly we question ourselves when things do not go the way we want and the rubber meets the road in terms of questioning your decision making. Looking back now, I am immensely thankful for that time as it has taught us that when life gets tough, you don’t give up, you just persevere. We find ourselves applying the truth of that lesson over and over as small business owners. Now that business is going well, we can speak to clients from a place of confidence because we know exactly how committed we are to our vision. More practically, it helped us learn even more about the cycles in the advertising business and that we need to be able to budget accordingly.

Hard Choices

In the middle of our two month drought of very little work we were also faced with tough choices. We had been planning on going on a family vacation to Minneapolis over the Labor Day weekend. We were going to go to the State Fair, enjoy some time outdoors and visit the farm that is still in my family. My Dad was even flying out to go on the trip with us to help with the kids and he was excited to go to the farm that belonged to his grandfather. We had the money saved for this trip, the kids were excited and we had made all of the plans. The problem is, as you now know, business was NOT coming in and we were questioning the wisdom of going on a vacation when things were not the greatest. We questioned it, debated it and at the end of the day we decided to still go. Looking back I don’t know that I would’ve made the same decision as the PF blogger inside of me cringes at writing this, but we had the money saved and could afford it from that perspective. The thing is though that the week we had decided to stay with going on the vacation, work started pouring in! Looking back, it was a turning point in our business.

When the Going Gets Tough Don’t Give up on Yourself

I share what I do because it’s almost always easier to throw in the towel, especially when things get tough. When times are tough you learn awfully quickly that motivation is not an issue as you’ll do pretty much anything, legally, in order to put food on the table for your family. I have also learned that I am my own worst critic, as many of us are to ourselves. It’s easy to criticize and wonder what you were thinking, especially when things are not all lollipops and rainbows. The old adage that anything worthwhile takes time fits very well here. If running your own business was easy then everyone would be doing it and everyone would be rolling in cash. But the nasty truth is that anything you want that will require work or sacrifice takes time and is hard work. Whether it’s paying off a mountain of debt, running your own business or training for a marathon, it’s going to require hard work and persistence.

Additionally, I would like to point out that there may be times where the wise decision is to question whether or not you’re going down the right path. Often times when you hear of individuals running their own business they can sound a bit delusional in thinking that they should never consider questioning what they’re doing or if they should perhaps go a different path in life. I love running our own business, but I have also learned that self-reflection is vital. The worst thing is, in my opinion, to continue down the path of doing something when the writing on the wall is telling you to stop. On the flip side, if you have a vision, or if you have a goal you’re striving for, do not let adversity hold you back. By growing through it and overcoming it to achieve your goal you’ll be a much stronger person in the end and ready to take on more difficult things as life throws them at you.


If you’ve made it this far, thanks for sticking around while I let my inner Tony Robbins out. What dream(s) are you holding onto but haven’t started pursuing yet? What’s holding you back from going for it?


Photo courtesy of: KathySmithFL

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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.


  • Great post and a timely one at that as I am contemplating going out on my own as well. It is both scary and exciting at the same time. I still haven’t made my decision just yet, but reading this gives me comfort to follow my dreams.

  • With any new business there is likely going to be periods of little to no work. That is half the reason why I still have my desk job, I am just not comfortable with doing things on my own just yet. Once the house is paid off any my wife isn’t looking after our son full time then things will be different.

    • John says:

      You’re exactly right Glen. Added to that is the seasonality of different sectors which I was not fully aware of in the advertising realm.

  • Great post John. I think there is value in evaluating what you are doing, as well as sticking it out and believing that things will work out. I definitely question how I use my time, whether I’m in the right job, etc. on a weekly or monthly basis. It’s important to be spending your time in the best way possible, even if it means going through some patches of seriously questioning your decisions.

    • John says:

      Thanks DC! I agree that there is value to doing that and I think there is a balance to be had in it. I don’t want to be blinded to just thinking that the current course is always the best course.

  • Dude, I didn’t know you were from Minnesota! I think half of the PF blogosphere is from there:)

    I’m sure that it is scary to go months without any money coming in. That is one reason why it is so difficult for most people to go out on their own. You have a lot of courage, my friend.

    • John says:

      Actually, we’re from Nebraska…Minnesota is only a few hours away and we go there quite often for vacations.

      Those months are scary, especially when you see nothing happen. Thanks for the kind words…hopefully it is courage and not downright stupidity. πŸ™‚

  • Well done John for plucking up the courage and going for it! I hear so many people who say that they’re going to start their own business but never get round to it, and like you say, if it was easy everyone would be doing it!

  • AverageJoe says:

    I’ve learned over time that there are two times in a work cycle: times when you load the guns (drive toward business) and times when you fire the guns (business comes rolling in). I’ll bet that dry spell ended up being “load the guns” time, didn’t it? Even my blog is the same way….if I work hard this week I’ll notice a surge in traffic about two weeks later.

    • John says:

      That’s a great point Joe! It was definitely a load the guns time. We look back and quite a few of our clients came in during that time and am thankful for the experience and what it taught us. Unfortunately life is not always a firing the guns kind of time.

  • pauline says:

    Oh, the freak out phase. Been there. Thankfully I didn’t need the income to eat but it was still weird to think you have a plan, and not fulfill it. But only sticking with it will tell you if it was meant to work.

  • I think one reason so many businesses fail is lack of planning. People get fed up, quit their job, and think they can do it on their own. They have no back up and when times are lean they are out there begging for a job again. I think you just have to know there will be lean times and keep a bit saved up for those. I’ve know realtors and construction workers who let the good times roll and when things slow down, they are looking for bartender jobs. Even in my business, I know the Christmas/New Year time is going to be very slow so we try to plan accordingly and put some money back throughout the year. If we hit a good holiday season, great, If not, at least we were prepared.

    • John says:

      I could not agree more Kim! That lack of planning can really come to bite you in the butt if you’re not prepared. We have a very similar seasonality in our business, which is why saving and always looking for new clients is vital.

  • What a great post John. I think your story will really help people out there who are thinking of starting their own business! It’s nice to know that it’s not all rainbows and lollipops in being your own boss but on the other hand the payoff could be immense πŸ™‚

  • I remember those days. When I was running my ecommerce company, there were months of great orders and new customers, but then it started to dry up. I was always running around frantic trying to figure out what happened. If you can stick to it and keep going, it shows your character. Many people would jump ship and start something else or get a desk job. Nice work John.

    • John says:

      I figured you’d be one of the ones who could relate Grayson. Yep, we were running around like crazy trying to figure out what on earth was going on. It was very stressful, but it taught us a lot about ourselves and our commitment to our vision.

  • Michelle says:

    I’m thinking about going out on my own as well and it’s a very scary thought. I feel like I’m ready but there are so many things holding me back.

    • John says:

      I remember that feeling Michelle. Part of my mind was screaming “What the hell are you thinking?” That’s why it was so helpful to come up with a plan and look at the numbers. The rest, as they say, is history. πŸ™‚

  • Mackenzie says:

    Great post John! I like what you said about “when the going gets tough, don’t give up on yourself”. Anyone wanting to take the plunge into self-employment, should read this post πŸ™‚

    • John says:

      Thanks so much for your kind words Mackenzie! That feeling when you want to give up, tells you a lot about yourself and the beauty is that it can be applied to so many things in life.

  • That’s the nature of the game with self employment, it takes a while to build a strong, RELIABLE client base and for recommendation of your skills to spread. Hope things continue to go well for you John.

    • John says:

      You’re exactly right Adam, it does take time. I think that knocks out a lot from going the distance with running their own business. Things are going well and look to be continuing. πŸ™‚

  • I love this because you know I can relate so much to this! I’ve very hard not to doubt yourself when the work stops…and it always seems to do that at one point in the year. Glad you hung in there!

    • John says:

      Yes, I figured you’d be one of the ones who could relate to this Tonya. It can be very easy to doubt yourself, and try as I might it still happens from time to time.

  • My Financial Independence Journey says:

    I don’t have any business dreams that I’m holding back. But I would love to quit my job and travel the world for a year. Of course, since finding a new job would be rather difficult, my dream remains a fantasy.

  • I started pursuing my dream just last week. I`ve always wanted to be a translator, and last week I found a job ad, searching for translators for a publishing comany that`s expanding this year. I applied and received a couple of tests, and today I sent in my translation tests, so here`s hoping!

    • John says:

      That’s awesome! What languages exactly will you be translating? It sounds like a very interesting opportunity. Good luck! πŸ™‚

  • Great post! Thanks for sharing your experience. I’m sure you have enough fund saved up to last a few months. That’s what I learned from talking to friends who were self employed. Business will be up and down so it’s important to have a strong reserve.
    How is the business now?

    • John says:

      Thanks! Yes, we do have a nice sized E-Fund and are working to grow it. We would not have made the leap otherwise as income is just too unpredictable. Business is going well for us now and getting new clients on a regular basis, thanks for asking!

  • Life is sure mysterious. How crazy that you would get offered a job at the company you had been trying so hard to get into right after you make the decision to start your own business? It is scary taking the plunge and being your own boss. I agree perservance is key. And knowing who your client is so you can market and build your brand to reflect them. I find some people go too broad to appeal to everyone and end up appealing to no one. Of course, you can’t go too narrow either. πŸ™‚

    • John says:

      That it is Shannon. I remember thinking what on earth is going on for me to get the offer at the time I did. The nice thing is that they were completely understanding and asked me to reach out to them if business did not work out as we have hoped. You’re right, finding the right appeal so you attract many is vital to have.

  • Ups and downs, but keep grinding away. You’ve got what it takes!

  • The Happy Homeowner says:

    I just went out on my own and I do fear the freak out phase–but I realize that things will be highly variable so I have planned for the downturns. That said, it doesn’t make it any easier to be on such a roller coaster ride sometimes!!

    • John says:

      That’s the key Jen, planning for those downturns. The freak out phase is inevitable at some point, in my opinion at least, but it does teach you a lot about yourself. No, the roller coaster is not easy, but it does make life interesting. πŸ™‚

  • John says:

    Great post John. My dream that I missed out on for quite a while was starting my own blog. As you know, I have recently started pursuing that dream. It is pretty scary and at times I feel like I am in completely over my head, but for the most part it has been a success. Thanks for the inspiring story.

    • John says:

      Thanks for your kind words sir! The nice thing about feeling like you’re in over your head is that’s it a great learning opportunity which helps you grow in the long run.

  • Justin says:

    It’s kind of funny that you posted this on the day when I wrote about my goals. Your situation of not enough works is why I really want these goals accomplished before I hand over my notice.
    I still want to pursue my dream, but definitely want to make sure that I’m ready for what that entails.
    Thanks for sharing your journey John. I love reading these posts because they give me a kinds of heads up on the future.

    • John says:

      Thanks for your kind words Justin! I was thinking the same thing as I was reading your post this morning. I can completely understand why you want to reach many of those goals before diving in head first. To do so would otherwise open you up to potential risks.

      No problems on sharing. I do so to give a realistic picture of what running a business is like. If you go into it unplanned, then you’re destined to fail in most cases.

  • Great post!
    I know that feeling all too well of wondering where did all the business go and what is waiting for us around the corner. I also found that when we thought we had new business I would start counting the money in my head and figuring out how to budget and allocate it long before we saw the actual payment. We quickly learned to request a 50% deposit upfront and not to count our chickens before they were hatched. Did that make things easier? Sometimes. The biggest thing, as you said is perseverance and knowing when to continue and when to say enough is enough. Congrats to you two for creating a successful business.

    • John says:

      Thanks so much Sicorra! I have been guilty of counting that money before we get it and am trying to teach myself not to do that, and I think that I have grown in that. We have also learned to request to deposits upfront, mainly from brand new clients that we do not know. Thankfully we’ve not dealt with people who have not paid yet, and hopefully will not….though I am realistic.

  • Great post John! I’m looking to start my own investment newsletter but keep procrastinating because I feel like there is always one more thing to do in relation to my blog.

  • Thanks so much for sharing your experience John! Really inspirational and encouraging what you have been working through. I’ve got some dreams of my own to pursue in the coming years but time and my wife’s current dream pursuit hinder me from going for them right now. One dream at a time.

  • I have a plan of venturing into a fashion accessories business with my daughter who loves hair accessories and trinkets but I am still holding on to the idea because I still need to develop my creativity further and learn how to do the more complicated ones.

  • Jim says:

    Great Post john, very motivational, thanks! I think you made the right decision to go to the farm in Minnesota, some things are worth going into a little debt for (if you have to) and you had saved for it. Good decision, the kids would have been heartbroken, and it was probably great bonding time, which is soooo important in raising a family these days.

    • John says:

      Thanks Jim, that was my hope! I wouldn’t have gone in to debt for it, but the fact that we had it saved was what cinched it for us. It was a great bonding time for us and glad we had the opportunity to go.

  • I happen to think Tony Robbins is a great motivational speaker. Funny thing is sometimes we can dish out the motivation but it’s very hard to motivate ourselves.

    I don’t own a business and I don’t know if I would be as courageous as you. You are a strong man John with a determination like no other. We can only push ourselves as far as we have the desire to succeed and the will to not let anyone or anything step in the way. There is no doubt in my mind that your business will grow John with the force you and your wife bring to it.

    You are one heck of a guy who not only helps others out but gives his 100% in everything that he does. Your children will understand one day what you did and why you did it. It’s all about family. Thanks for this great post mate.

    • John says:

      Thanks for the kind words Mr. CBB! I try to give all I can and leave everything out on the court as they say. To do otherwise would just be robbing ourselves of possibilities for myself and those around me.

  • I have plans to add a project or two to my web business with the goal of early retirement. At some point I will have to make the decision to quit my day job, hopefully it won’t be as stressful as yours! Glad your decision has worked so well for you John!

    • John says:

      That sounds great Paul, I hope it works out for you! Speaking as a business owner though, good luck finding a stress free business. πŸ™‚

  • Catherine says:

    Great post! So glad everything worked out for you and your family. Good things happen to those who wait πŸ˜‰ You were persistent and all your efforts clearly paid off.I hope it keeps up!

  • “If running your own business was easy then everyone would be doing it and everyone would be rolling in cash”. So true! I don’t own my own business yet, but would like to do so in the next few years. I’m sure it’s terrifying for a while, but I always tell myself if worse came to worse I could always work per diem in my current industry. Thanks for sharing!

  • I do want to go to grad school, and I’m starting to believe that I’ll never get hired in the industry I want to pursue without additional training. It is theoretically possible, but after 3 years it just isn’t happening. The problem is, of course, that I simply can’t afford graduate school without substantially paying down some debt.

    • John says:

      What industry were you looking to go into Edward? I can relate as I paid down my debt before I went back to grad school. The loans are bad enough, if you have to take them.

  • Alexa says:

    Its easy to question yourself when times get tough, but it’s also a good time to question yourself. Some people can’t take the uncertainty that sel employment brings, which is perfectly fine because we are all different. But you are right everything worth having takes time to get, no one is born an overnight success.

  • Andrea says:

    I’ve written a couple of times about the way that money seems to roll in at exactly the moment that I think all is lost and I won’t be able to make it. There have been times, especially in my first year of self-employment, that I was staring at my bills the day before they were due and didn’t know how I’d pay them. As others have mentioned, those are the times when the best ideas tend to come out of hiding, when you have the most power to see how much you can really do.

    There are days that the stress is so great I feel like my head will explode, but those moments just make me even more determined that I will never work for someone else again. I appreciate your honesty re: the vacation – sometimes you have to do things because you need to, even when common sense might tell you otherwise. I really love this post series; there’s so much great information here for people who might be struggling or considering self-employment.

    • John says:

      First off, thanks for your kind words Andrea! I can really relate to your feelings. We weren’t quite at that point you described yet, but it was definitely in sight. I would agree that it is those times that some of the best ideas come to the surface and help build long term steam.

      I can also relate to that stress, and is something that you can’t truly know until you’ve been in the trenches of running your own business. It allows you to learn so much about yourself and what drives you. For me, it was wanting to see success and not wanting to work for someone else ever again. That freedom, though stressful, is quite intoxicating from my experience. I would agree about the vacation. The PF part of my mind thinks it was foolish, but the more rational side of me sees that it was a great time to get away, refresh and come back ready to attack it with all we had.

  • Inspiring story. You just got to keep pushing if you know something if it’s your dream. Those are just tests to see you much can you go on. But hey, you came through. You made it. Although, I got to say, that photo got my attention first. Oh boy I really want to try sky diving.

  • CF says:

    One of the big things I’ve been meaning to do is to finish my book. I used to be very diligent in writing a few hundred words a day, but just haven’t had to energy to finally FINISH it.

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