7 Life Lessons I’ve Learned Since Becoming an Entrepreneur

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I've learned a lot since taking the plunge and becoming an entrepreneur. I share 7 life lessons here.

I have a confession to make. Ever since I can remember I have wanted to work for myself. I wanted to be an entrepreneur. I don’t know why that’s the case, but it’s something I’ve noticed for years.

The funny thing is, I never thought I had it in me to become an entrepreneur. In all honesty I think fear held me back.

Fear of the unknown.

Fear of it all blowing up in our faces.

Fear of what others might think of us taking the plunge.

I’m sure there were and are other fears, but that’s a topic for a different day. As I come upon three years of being an entrepreneur on my own and being a part of it with Mrs. Frugal Rules for a little over five years, I see one constant – there isn’t a day that goes by where I don’t learn something about working for myself or a life lesson in general.

With that in mind, I wanted to share some of the top life lessons I’ve learned since becoming an entrepreneur in the event it’s something you’re considering. If it’s not, then hopefully you can still get something out of it as it’s not all necessarily related to being an entrepreneur. 🙂

Life Lessons I’ve Learned Since Becoming an Entrepreneur


Opportunity is out there for the taking. Before I took the plunge into working for myself I knew the opportunity was out there, but had an admittedly academic view of it. Meaning, I was limited in my understanding of it.

Looking back, I now see how this held me and us back as a family. I thought that opportunity was only something special people got. Oh, how I was wrong. Yes, there is some luck involved in my opinion, but much of the opportunity is out there for the taking. Yes, it does take work and time to find it at times but it is most definitely out there to be had.

In my pre-entrepreneur life I see how this became a self-fulfilling prophecy far too many times. Today, I see opportunities as something to look for.

They’re something to fight for.

They’re something worth discovering.

They lead to more opportunities.

Even if you don’t work for yourself, I think this is something that can be applied to many areas of life. Instead of limiting yourself an “I can’t do that” mentality, think: “I wonder what X,Y or Z would look like if I tried it.”

Almost anyone can be an entrepreneur. The above lesson somewhat bleeds into this one. As I mentioned in the beginning I never thought I could be an entrepreneur. I thought there was some special skill I was missing, that I didn’t have the right personality, or that I couldn’t crack the special code.

Sadly, sarcastically speaking of course, I’ve discovered there’s no special decoder ring or anything like that you get in being an entrepreneur. It isn’t a special club. If I can do it then I know many others can too. That’s not to say you should start working for yourself, but that it can be done and can be done quite well.

If it’s something you want, don’t hold yourself back by the belief you can’t do it. I’m evidence of the fact that it can be done.

Being an entrepreneur isn’t for everyone. I’d be selling you short if I didn’t follow up #2 with this lesson. I’ve shared extensively about the things I hate about working for myself. I’d be selling you short if I said that being an entrepreneur is all puppies and lollipops – because its not.

As much as I or anyone else for that matter, touts working for yourself, it’s just not for everyone.

Businesses fail.

People lie to your face.

You’re on the line for everything.

That can be an incredibly overwhelming burden to shoulder, especially when you have little ones to provide for. Mrs. Frugal Rules and I know exactly how overwhelming that can feel. There are days where I want to just hang it all up and shutter our business and get a “real” job in the traditional workforce. However, I quickly wake myself up with the realization that it is just not for me. While society glamorizes working for yourself, it’s most certainly not for everyone.

Money isn’t everything. I know, this is a personal finance blog and I’m saying that money isn’t everything. Throw stones at me, but it’s the truth. Money isn’t everything.

There are other things I’ve come to appreciate much more like traveling as a family. Money can be a funny thing with entrepreneurship – you rarely know where you’re next client is going to come from. If you’re like me that means wanting to take every job or do jobs that don’t pay you as much as you’d like.

Of course, you can only go so far doing that and thus why it’s so important to know your value. It means being open to firing a client if they’re not worth the hassle. It means realizing that you need to reclaim time for yourself as working for below what your worth is going to get you nowhere quick. I believe this can be applied to entrepreneurs and those in the traditional workforce. Know your value and be able to quantify it as that gives you power.

Embrace risk. Many would argue that being an entrepreneur involves risk and they’d be correct. There is risk involved. As I get, cough cough, older I see that risk is all around us. It’s what you do with that risk that helps or hinders you in my opinion.

You may not work for yourself, but risk is everywhere. Some of that risk, like investing in the stock market or asking for a raise, should be done wisely. Other risk, like telling your kids to go play in traffic is stupid risk and should be avoided at all costs.

Prior to taking the plunge myself I did all I could to avoid risk. I don’t know if I was fearful of it, but I definitely did what I could to avoid it. That has changed for me now. Admittedly, I still have a lot to learn when it comes to this but I’ve also come to realize that if I want to live a life of purpose and reach the goals we have as a family then I need to assess risk and welcome it when it means the possibility of taking us where we want.

Temptation doesn’t have to take you down. I’ll be honest here…the first year or so of our business there were times when I didn’t know what was going to happen financially. Fast forward a few years and we’ve had back-to-back record income years for us as a family with strong prospects of another similar year this year.

If that would’ve happened to us almost 15 years ago I’m quite certain of what would happen. We’d have spent all we could on different things, err crap, that we wanted. That’s not the case now.

Yes, we do allow ourselves a few simple pleasures as we put in a lot of hours but it’s all within our budget. We seek to enjoy today, without giving in to the belief that such a mentality equates to spending money like fiends. Rather, we enjoy life reasonably while focusing heartily on the future. That’s not to say that we haven’t been tempted at times, because we have, but realizing that temptation comes at the expense of our future helps keep us from making foolish decisions with our money.

Your temptation may be something else, or it very well could be financial in nature. The point is to act with prudence and to keep your eyes on the present AND the future – it can be done!

7 important life lessons I've learned since becoming an entrepreneur.

There is no one else I’d rather do it with. I saved this one for last on purpose. 🙂

I know it may sound cheesy.

I know it may sound sappy.

I know it may sound as not being possible.

But, it’s the truth, I couldn’t imagine going through this wild ride of being an entrepreneur with anyone other than Mrs. Frugal Rules. We get odd looks at times, but we seriously love working with each other. I know it’s not for everyone, but in our opinion we’re married so why wouldn’t we want to work together? Taken further, we’re both obviously different so our strengths and weaknesses play off each other so we’re that much more effective as a team.

In all honesty, Mrs. Frugal Rules is the backbone of the business. I don’t share this often with many, but she had left her a career as a copywriter after we had our third child. As a way to fill up a little free time (which I have no clue what that is anymore) and a way to bring in a little more income for the family she started freelance writing.

Some of you may remember them, but her first writing gig was through Demand Studios. Yes, that Demand Studios, who only paid $15 per post for the most random and inane posts before they got a huge slapdown by Google.

We were thankful for it at the time as it helped provide for our family, but the writing was soul-crushing. Long story short, it was needed as our first major client we assumed we’d get fell through. She wrote for Demand Studios for nearly ten months. I hated having to see her write the crap they had her writing and wanted it to be done for her. Coincidentally enough, the Google smackdown essentially resulted in her not being able to write for them anymore. That is the best thing that could’ve happened for us as a family.

Fast forward five years and we’re now doing marketing campaigns and strategy, plus considerably more, for companies all over the country, small businesses here in Omaha and several international businesses. Much of that all is because the gem my wife is and the backbone she is for our business.

Ok, enough cheese. 😉 I’m sure there are other life lessons I’ve learned over these past number of years. In fact, I know there are and this list only scratches the surface. The point is that life is full of learning opportunities and it’s what you do with them that matters in my opinion.



Do you want to or envision working for yourself? If you do now, what is one of the top life lessons you’ve learned as an entrepreneur? Why do you think society tends to glamorize being an entrepreneur?

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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.

Latest posts by John Schmoll (see all)


  • Jayson @ Monster Piggy Bank says:

    John, sometimes it is our calling to be an entrepreneur. Some people may not realize it earlier. That being said, I think we should just take every opportunity at hand and try it out. There’s no harm in trying. Being more sensitive really helps most of the time.

  • Holly@CLubThrifty says:

    I agree with all of these. And yes- opportunity is definitely there for the taking. The people who get out there and come up with creative ways to capitalize on their ideas or skills are the ones who succeed.

  • MyMoneyDesign says:

    Great way to end the post! 🙂

    The more I talk with people who have actually made it as entrepreneurs, it seems the more it has to do with their ambition over anything else. It sounds to me like you guys certainly fit the bill.

    • John Schmoll says:

      Thanks MMD!

      I would agree – ambition definitely plays a role in it. I know, personally speaking, that ambition can wane at times which is why it’s so important to keep the “why” ahead of us.

  • DC @ Young Adult Money says:

    Great tips, John. I would say that I have the entrepreneurial bug and have had it since high school. With that being said, I don’t like what I’d have to give up to pursue that path. That’s why I think side hustles and doing projects/businesses on the sides is ideal, at least until one of them “takes off.” If one of them never “takes off” and becomes my full-time job I don’t think I’d be disappointed. The only thing I would regret is if I never tried!

    • John Schmoll says:

      Thanks DC. You have a valid point – there is a lot that to give up and taking the side hustle approach can help in a lot of areas. I think it can help you balance the reality (to a certain aspect) of working for yourself while also trying something out.

  • Shannon @ Financially Blonde says:

    You are definitely speaking to me on this one John. I think the biggest thing I hate about being on my own is having to deal with people who are not as honest about their business as I am. I have been burned more times than I care to reflect on and it sucks but it also gives me greater conviction to not run a business like them and take the higher road. I truly believe in karma and I hope to put out good karma in the universe no matter what bad karma people send my way. It just helps me sleep at night and look in the mirror every day.

    • John Schmoll says:

      Yep, that drives me nuts as well Shannon. We pride ourselves in doing business the way we like to receive it. Sadly, there are many who don’t feel/act that way. Like you said though, it just makes us want to take the high road even more.

  • Laurie @thefrugalfarmer says:

    Awww, so sweet what you said about Mrs. FR. 🙂 Personally, #1 has been huge for me. It tells me that NO ONE can stop me from being an entrepreneur should I choose to be one.

    • John Schmoll says:

      Could not agree more Laurie! I think it’s something that we can really only stop ourselves from doing.

  • says:

    I know that I will learn more from trying and failing than NOT trying at all but what if I fail!?!?
    I have a handful ideas that I want to get going on but sometimes the fear is paralyzing. I love the honesty in your articles. Thanks.

    • John Schmoll says:

      Thanks for the compliment Rebecca!

      I totally understand that fear of failure. I still deal with it regularly – I’d be lying if I said I wasn’t. I try to use that to drive me, even more so now that I see a lot of my original fear was unfounded – mainly that “the worst case” would never really happen because we set things in place to protect against it.

      Maybe you could try starting with one of the smaller ideas that don’t require as much time/resources and go from there. I find that if an idea has proven to be successful that it helps build momentum towards others.

  • Kim@Eyesonthedollar says:

    I think the difference between people who can work for themselves and those who can’t is attitude. Some people need a set schedule dictated by someone else and need to be told what to do. Others are able to seek that out on their own and don’t have a problem with charging for what they are worth. I don’t know that one way is for sure better than the other.

    I used to write for Demand Media as well. The health section paid better than $15, but it still was a roller coaster. I got fired out of the blue, then they asked me to come back. Then a few months later, I was fired again. I think with those jobs you just have to milk them for all you can and not count on them being there the next day.

    • John Schmoll says:

      Good point Kim. I’d agree that one really isn’t better than the other. So much of it depends on what you work best with and where you can take it.

      Yep, DS was a huge roller coaster for us. The editors were all over the board so she never knew what to expect and that’s not to mention the crazy things she was writing on. We needed the money at the time, so it took care of us, but very thankful they ended up letting her go.

  • MarieMakesCents says:

    Deciding what level of risk to take has always been hard for me, so when I quit to go freelance this year I was having a little bit of a panic attack. And then my main client backed out. haha.

    I know I made the right choice for my family going down the line, but being an entrepreneur is definitely not for the risk-averse. You just never know when you’ll land on your ass. Of course that also means you never know when an amazing opportunity will appear either. You just have to trust to your strengths and keep on plugging away!

    • John Schmoll says:

      I could not agree more Marie! Opportunity cuts both ways and there are times where you completely lose out and others that you can’t believe you’re getting it. That plugging away, in both instances – as well as the times in between, is vital.

  • Mark@BareBudgetGuy says:

    John – Keep these posts coming. They are helping me necessarily adjust my mindset. I am getting close.

  • Shannon @ The Heavy Purse says:

    I love how well you and Nicole work together and I’m so glad you took the risk and became an entrepreneur. While I absolutely agree it’s not for everyone, I’m glad I took the risk too. It’s helped me provide a good life for my family and for my employees too. I take just as much pride in seeing their earnings increase and being able to buy homes, etc. because of our good work together.

    • John Schmoll says:

      I do as well Shannon. I know it’s not for everyone and count ourselves as blessed to be able to do it. I feel the same way about seeing others be able to do well because of what we’ve done as a team – it just makes me want to do it more.

  • Jason B says:

    I want to get back to working for myself again. I tried it out for a few months last year and lets just say it was a learning experience. One of the things that I learned was that there is always opportunity out there. You just have to be ready to work your tail off.

  • Michelle says:

    I love love LOVE this post! Being an entrepreneur is definitely not for everyone, but it is well worth it to me. Every day I wake up thinking about how great life is now that I know what I want to do in life.

    • John Schmoll says:

      Thanks Michelle! I feel the same way about what we do. I still pinch myself at times thinking I’m going to wake up and realize it’s all a dream…thankfully it’s not. 🙂

  • Dividend Mantra says:


    Great post.

    Couldn’t agree more that fear holds many back. I know it was the same for me until I quit my full-time job in the auto industry last year to pursue writing full-time. And you’re right in that the opportunities are out there for those ambitious enough and those with open eyes. Sometimes you just have to take the plunge and see if you can fly. 🙂

    Best regards!

    • John Schmoll says:

      Thanks Jason!

      You hit the nail on the head – sometimes you just need to take that leap to see what you can do. As you know, it’s not necessarily easy but it can be done. The challenge, I find at least, at times is to keep that focus on continuing to fly and not getting comfortable.

  • Mrs. Frugalwoods says:

    I love your story, John! Mr. Frugalwoods and I feel exactly the same way–why wouldn’t we want to work together :)? We’re really looking forward to collaborating full-time on the homestead. It truly is one of the main motivating factors for us in making the move.

    Makes me so happy to hear about how you and your wife have created such a wonderful partnership, family, and business!

    • John Schmoll says:

      Thanks Mrs. FW! I know – we feel the same way. We get goofy looks at times, and sure, nothing is perfect but we love it and just further strengthens our marriage relationship.

      I’m confident you and Mr. FW will have, well you already are :), the same thing once you go FT on the homestead.

  • Gen Y Finance Guy says:

    I too have that burning sensation deep down that is pulled towards entrepreneurship. I have done many side hustles that have brought in good money but nothing good enough to release me from the golden handcuffs of my cushy 6-figure corporate job.

    In the meantime I try to master the blend until I can eventually make the break.

    I am also leveraging that cushy job for the nice cashflow it brings into the household.

    My ultimate goals are: Time Freedom, Location Freedom, and Financial Freedom.

    Congrats on 3 years of success.


    • John Schmoll says:

      That’s the challenge many face, in my opinion at least, of keeping that balance in mind and being patient.

      Kudos to you for leveraging what you’re currently making to help towards the transition – that’ll help you in many ways down the road.

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