Think About Working for Yourself

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Think About Working for YourselfWhen I was coming back from vacation last week, our seating got a little screwed up.  Long story short, I ended up sitting next to a lady in her mid-fifties from Alberta, Canada instead of sitting by my wife and daughter.  We got to talking and had some really good conversation throughout the flight.  At one point, I mentioned something about my 9 to 5 job and she chuckled.  It turns out she’s a consultant and speaker on business efficiency.  And she talked about how valuable working for yourself can be.

She’s made a really good life for herself and works when she wants to, loves what she does, and makes outstanding money.  I was so excited for her just hearing about this.

Coincidentally, while I was on the plane, I was also reading The Millionaire Next Door (a really good book!) and I came across a passage that seemed to match my conversation with my airplane neighbor:

There are more people [employees] today working at jobs that they don’t like. I’ll tell you honestly that the successful man is a guy who works at a job, who likes his work, who can’t wait to get up in the morning to get down to the office, and that’s my criteria. And I’ve always been that way. I can’t wait to get up and get down to the office and get my job under way.

I showed her the passage and she said that’s exactly how her life is right now.  Although it can be a lot of hard work, particularly at first, the payoffs can be tremendous: freedom to work when you want, possibly better income, happier while working, etc.  If you can find something you love to do and get paid to do it, it’s hard to call it work anymore.

If you’re young, that’s the best time to start working for yourself.

One of the best times to start working for yourself is when you’re young.  That’s because you likely have the motivation, the energy, and the drive to do it.  Don’t put it off, because as you start to get older, not only do you lose some of that energy, but things get in the way.

What do you mean by “things get in the way”?

I mean exactly that – life happens.  Consider this…

Before long, you might find yourself getting married – which now means you and your spouse need to be in agreement if you want to start working for yourself.  Then you might have kids.  Kids are awesome – but they take away a lot of your time and energy.

Ok, I get it, but I’ll still have that drive and determination to do it when I’m older.

Maybe you will.  But as you get older, something else can easily get in the way… you make more money.

I love making money, Jim – this sounds great!

Yes, but that’s the problem.  If you start making good money, you might think “why would I leave this job to struggle starting a business when I’m raking in the bucks here?”  Complacency starts to take over and you become stuck.

I can vouch for all of the above because that was exactly how things went for me.  And I don’t regret the path I’m on because I’ll still be financially free before long, but I will tell you that I could have reached that goal a long time ago if I had started a solid business and built it up when I was much younger.

It’s never too late to start working for yourself.

I was always intimidated about the idea of starting my own business.  I really think the idea of having employees was what turned me off to the notion of working for myself.  Unfortunately, like many people, that fear caused me to just keep doing what I was doing.

I’ve always been a hard worker and seem to find myself bumped up to middle management at some point with every place I find employment.  Eventually, the hard work started to pay off for me – I now make a nice salary and have a 9-5 job doing something I’m good at.  And I enjoy my job, but that’s it – I have no control over the direction of the company.  I’ll continue to make good money, but I’m never going to be rich working for someone else.

So where do you go from here?  I’m a little older, have a child about to start in the first grade, and a wife that works part-time.  It’s easy to get complacent with a job that takes care of you and your family.  And that’s exactly what happened to me for a number of years.  But the craving to reach financial independence at an early retirement age and the desire to be able to pass on something worthwhile to my daughter has pushed me forward.

I’ve mentioned before that I’ve written and published a couple of technical books and I’m very happy that I did – it’s something you can really be proud of and definitely gives you a huge sense of accomplishment.  To do it my way, I formed a publishing company as well.  I basically built a business.  Sounds great, right?  I blew out my goal on the number of books to sell and kept more of the profits because I owned the publishing company.  However, it’s extremely difficult to become a wealthy author.

In another situation, my new business has started to grow organically into a real estate company.  I started with one rental house and didn’t do much with it.  Then I purchased the duplex more recently and decided as of late that I needed to protect our interests in these investments.  So we’ve formed an LLC and re-deeded both properties to be titled under the new company.  We’ve also purchased some additional insurance (an umbrella policy) to give us a little more protection from any goofy lawsuits – like if a tenant breaks their leg while on our rental property and tries to sue us for it.

Although not your traditional type of business (like consulting, for instance), I’ve grown more and more excited about real estate and this is a good way to make this happen.  My game plan is to purchase a few more multifamily properties before I quit the 9 to 5 job.  The beauty of this is that I’m slowly building a solid team as I go – real estate agent, mortgage broker, property management company, insurance broker, handyman, etc.  My job is going to morph into mostly finding the deals and making the magic happen.  It’s not to say that it’s not involved, but the team will handle most everything with my direction.  So I don’t have the employees I was concerned about and the time I’ll put in shouldn’t be too much if I don’t want it to be.

Now that’s just what I’ve figured out over time for myself, but there are so many great opportunities out there.  If you’re trying to become financially independent, starting your own business can be a great avenue to make this happen more quickly.  You just need to find what makes sense for you.

Are you currently your own boss and working for yourself?  If so, do you enjoy it?  If not, have you thought about pulling the trigger and making it happen at some point?

Thanks for reading!!

— Jim

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17 thoughts on “Think About Working for Yourself”

  1. Jim – I’m not working for myself, but everything you’ve said resonates. Being the owner rather than the employee is the way to go. With a high income, I do feel the golden handcuffs. It’s hard to leave when you know you’re making good money. Thankfully I enjoy my job, so that helps, but I still think I could be making more money on my own.

    1. It’s a funny catch 22 that you get stuck in as your income increases – that’s why I think it’s an easier thing to do when people are younger and their income is generally not so high.

      — Jim

  2. Hi Jim,
    We have been landlords for 25 years but I never really looked at it as a way to move out of my full-time job (teaching). “Once a teacher, always a teacher” – especially due to the length of service required for pensions (and loving kids and what you do!) We now own a duplex, single family, and 8 unit apartment complex and we manage them ourselves. Just had an investor (who had contacted us – it wasn’t listed for sale) look at the 8 unit place yesterday – so we may have a decision to make about selling. Your post made me think of a quote from Warren Buffett that I head at the latest Berkshire Hathaway meeting – “I did decide early in life that my favorite employer was myself”! Great post!

  3. Hi Jim

    I really enjoyed this post. I totally agree what you say about it being harder to leave a job when you are older, I see that a lot when people earn high salaries, it is daunting to go from that to very low earnings in the initial phase.
    I have also looked at property and think you are doing the right thing, but personally I prefer stocks as I do not need leverage. At the moment I see myself as having my ‘own business’ by finding high yielding, high growth stocks, which are good businesses themselves. For example I have a stock that owns the Burger King franchises in South Africa. I see my stocks as a ‘mini Berkshire Hathaway’, and is my form of ‘business ownership’.

    1. Thanks, DT – it’s funny that you mentioned the stock side of things. I’m on the other side of the fence – the stock market scares me. I like the idea of dividend stocks and have been putting more money toward them, but just this morning, I started contemplating if I should stop contributing to my Roth IRA and start putting more money to rentals instead. 🙂

      — Jim

  4. This one strikes home for me. Family definitely happened to me, and now my “high paying job” is the one thing I can’t leave. I’m realistic, it’s currently my best path to Financial Independence, but I can’t help but dream of what would have happened if I had taken my side gig to the next level. Well, maybe once I’m FI…

  5. I’m half my own boss. I have my own LLC and sell my services, but am still temping full time to pay the bills while I build up my business. The biggest reasons for creating my own company was wanting to control the type of work I do and how I do it. I love my adorable little office – even though it is under 200 SF and has a skylight instead of a window. It’s mine and it feels like home.

    1. That’s awesome, ZJ! Being your own boss is the way to do it – hopefully you’ll get the business built up enough down the line to kick the other job to the curb! 🙂

      — Jim

  6. Jim,

    Couldn’t agree more. As you continue to work a “real” job, it’s easy to start accumulating obligations – mortgage, cars, kids, etc. I like to call it the success trap.

    Having your own businesses is a great way to slowly escape the trap. It can also help relieve stress you might have at your day job. Multiple income sources is always better than one.

  7. The golden handcuffs are real! We talk about this often, how we wish we had struck out for ourselves when we were younger and less chained to the higher earnings that let us stay on the FIRE fast track. If we’d made the leap when we earned less, we wouldn’t have felt the pain of the big drop in income, and we feel like we missed that boat. But, the good thing in our case is that we can redefine our lives however we want once we retire next year, and we’ll definitely do some amount of working for ourselves, it will just come without the pressure of *having* to support us, since we’ll have socked away our nest egg in advance. 🙂

    1. It’s a weird little trap, but it seems to have worked it will for you! I’m so excited for you guys to be able to retire next year – and I can’t wait to hear about the adventures you get into once you’re there!

      — Jim

  8. Currently I do feel like the CEO of my own life. I have been retired for 18 months.
    However long term, there is still some building required to free me from potential employment.

    For example, if I return to employment, my mentality will be more on saving funds for investing and opening a business or two.

    I got to a point where I’m mortgage free so don’t really feel like I am at risk. I currently have two properties, so would now like to try and be entrepreneurial.

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