When I decided to pull the plug on my job at the end of 2015, there were a lot of thoughts running through my mind.

On one hand, I was terrified.

The idea of FINALLY quitting my job was something I had thought about for years, but it wasn’t something I actually considered doing until about 12 months ago.

When I started looking at self-employment like a REAL, legitimate option for my future, a lot of conflicting thoughts came into the picture:

  • Am I truly capable of surviving without a full-time job?
  • What if all of my businesses fail and I suddenly stop making money? What then?
  • What about health insurance? Do I really want to pay for that myself?
  • What about all the other benefits my employer covers for me?
  • What if I have to go back and get a job someday? Would I ever be able to cope with a crushed spirit?
  • Is it foolish to think life can be this great? I don’t know anybody who gets to live like this… what makes me so special?

In a lot of ways, I was scared to let myself think big.

I think subconsciously, I was trying to keep my dreams under control, almost in a self-sabotaging way.

At the same time, when I pulled the trigger and gave notice to my employer, my new life sounded so unbelievably amazing – I could already taste the euphoria of freedom. The idea of doing my own thing and being completely independent sounded amazing beyond words (even as I write this 6 months later, I still have to pinch myself – because it really is that awesome).

The Self-Employment Mindset

Soon after I was on my own, I started to think about time and money a lot differently.

With an additional 40 – 60 hours to devote to my business endeavors each week, it was CRAZY how much more I would be able to accomplish.

About a month after I set the sails, I was interviewed by my friend Sharon Vornholt on how it was going. You can see that full conversation here…

After so many years of carefully budgeting our household income and living within the confines of my paycheck, it was a big revelation to realize that ultimately – there is no technical “limit” to my income (other than the limits in my own head).

With the complete independence that comes with running my own gig (e.g. – deciding which deals to go after, choosing where to spend my time, doing work that sounds like fun and NOT just what makes money), it occurred to me that there is very little holding me back from making whatever income I deem appropriate.

The Highs and Lows of Self-Employment

As with anything, being on your own is a mixed bag. Ultimately, I’d say there is a MUCH bigger upside than a downside – but nothing is ever as simple as “all good” or “all bad”.

The Highs

Thoreau1Freedom: The freedom has been incredible. Every day is an adventure that I can’t wait to begin because I always get to work on the things that matter to me. It’s probably the most “in control” I’ve ever felt of my own life and I thank God for it every day.

Loving the Work: I cannot tell you what a breath of fresh air it has been to lay in bed on Sunday night with a smile on my face, because I can’t wait to get to work on Monday. It has made me realize how important it is to do work that I love. It makes every aspect of life more enjoyable.

Money: Since leaving my job, my monthly income has gone up and down a bit… but on average, I’ve earned about 3x more than I was making from my day job. I was fairly confident this increase would come about, given the additional time I’d have to spend on my business, but I was also a bit nervous about how things would pan out because as the sole breadwinner of my family, this new gig HAD to work. There was no room in the equation for “maybe”.

The Lows

Taxes: Having done some sizable land deals in the past, I was already familiar with the unpleasant task of writing a MASSIVE check to pay my annual tax bill. Being 100% self-employed has only increased this pain. However, now that I’m in the habit of making quarterly payments to the IRS (and knowing this unpleasant task is always just around the corner), it has helped me to plan for and anticipate the “pain”.

As an employee who collected a paycheck for so many years, my taxes were automatically withheld from each paycheck, so it was easy to overlook how much was being taken out of my pocket each year… but when you have to manually write the check, it’s harder to be blissfully ignorant of the situation.

If anything, it shows me the importance of buying more cash flowing rental properties (i.e. – tax shelters) as part of my long-term business strategy. Land is great for a lot of reasons, but one of the few unfortunate aspects of a concentrated land portfolio is that tax breaks typically don’t come with the package (at least, not like they would with a dozen rentals or an apartment building).

Health Insurance: Similar to the tax issue – health insurance was something I hadn’t spent much time dwelling on as an employee. Fortunately, I was surprised to learn that the cost of health insurance wasn’t nearly as bad as I thought it would be (with a high deductible plan tailored specifically for my family, the monthly cost is about half what it would have been if I had chosen the same group plan from my employer). Nevertheless, it’s been another mildly annoying bill I never had to think about in my day job.

Peaks and Valleys in Revenue: When I was calculating the feasibility of working on my own, I took some time to figure out how much money I’d have to earn per day in order to match the income from my steady, predictable paycheck. This information has been a blessing and a curse because for every day I don’t meet this “daily quota”, it has been easy for me to get a little nervous.

I’ve been learning NOT to look at my daily performance but instead, to look at my monthly (and even quarterly) performance – because no business ever earns an EXACT amount of revenue every single day. Some days are fat, some days are skinny, but to date, every month’s (not day’s) performance has FAR exceeded that of my job, which underscores the importance of looking at the big picture.

Lessons Learned

When I used to ponder how great self-employment would be, there was always this underlying assumption that life would be perfect.

Even though the freedom and love of my work have been great, I can confidently report that I still have problemsI still worry about things. I still have frustrations. I still struggle with managing my time well. In a lot of ways, many of the same problems still exist in my life. The only difference is that I have the freedom to prioritize which problems to address and where to focus my attention at any given time. Life is certainly more enjoyable, but it’s still far from perfect.

As I’ve mentioned before, there’s a BIG negative stigma that some people have towards JOBS (i.e. – people who aren’t doing their own thing full time). Jobs are something most entrepreneurial and “business opportunity” folks love to bash as if they’re a symbol of slavery, mediocrity, or the biggest thing holding people back in life. I think there’s probably a seed of truth to this, but it’s also a one-sided perspective.

Having been out of my job a while now, I can safely say that full-time entrepreneurship is a wonderful fit for me, but I don’t think it’s necessarily the best fit for everyone.

Most people don’t acknowledge the fact that it can be very hard to go it alone. There are MANY more things to worry about when you’re a self-employed person, and when things don’t go according to plan, the stress can be much more significant than what comes with a standard day job.

Don’t kid yourself – there are PLENTY of things about running your own shop that isn’t glamorous and are very challenging in and of themselves. Some people are born with the mindset to handle this kind of stress and some aren’t.

In many cases, it is significantly less stressful and more enjoyable to be an employee rather than an employer – and that’s okay. Working under someone else can help you get your bearings until you figure out what you’re doing. That precisely was what I did for 10 years and it was a great fit for me.

At the same time… the freedom that comes with self-employment is something a lot of people never allow themselves to seriously consider. For some people and some personalities, a job will simply never be the right fit – and if you think you’re one of those people who has never felt “at home” in your job, I’d encourage you to keep exploring and creating new options for yourself.

The idea of completely obliterating these barriers would’ve been unthinkable for me 5 years ago – but in my first six months of this new adventure, I’ve learned that it’s very real and very much worth the leap of faith… but as with anything, there is a mixture of pros and cons that come with the territory.

The added costs and hassles of self-employment aren’t always easy to be deal with, but in my mind – they’re TOTALLY worth the trouble. When my freedom is at stake, I’ll deal with these headaches all day long. 🙂

The Best Real Estate Investing Strategy I’ve Found

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Land investing (that's right, buying and selling vacant land) is a massive opportunity that most investors aren't paying attention to. For the few land investors who know how to pursue this business with the right acquisition strategy, it's an extremely lucrative and low-risk way to build serious wealth from real estate.

If you want to get the inside scoop on how to start and run your own land investing business, come and check out the Land Investing Masterclass – where I've put together a full 12-module course with dozens of videos, bonuses, downloads, group coaching sessions and a members-only forum (where we spend time answering questions every week). There is no better place to learn this business from the inside out!

About the author

Seth Williams is a land investor with hundreds of closed transactions and nearly a decade of experience in the commercial real estate banking industry. He is also the Founder of REtipster.com - a real estate investing blog that offers real-world guidance for part-time real estate investors.

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  1. Al says:

    Good stuff. Proud of you

  2. Mary says:

    Congratulations! Would you mind discussing health insurance? This has been our biggest barrier. Thanks so much for sharing and inspiring!

    1. Seth Williams says:

      Thanks Mary! Health insurance is one of those things that sounds confusing and overwhelming on the surface, but I got a lot of clarity when I just called a local insurance agency and had them give me a few options at varying price points. I found that the cheapest options weren’t all that bad for my family’s situation – and given that I could get it tailored specifically to my needs, it ended up being even better than my employer’s.

      I’d definitely recommend calling a local insurance agency, talk to them about the scenario of working on your own, give them an estimate of what your annual income will be and figure out what will be offered at some of the different pricing options. You might be surprised that it’s more affordable than most people assume.

  3. Tom says:

    Thanks for the straightforward assessment! I’m curious as to how long it to the length of time from when you started working with land to when you pulled the plug on your job.

    1. Seth Williams says:

      Hi Tom – it took about 8 years of working it on a part-time basis. Also keep in mind, it wasn’t just the land business that allowed me to do this… land investing has definitely played a crucial role in the structure of my income, but I’ve also diversified into other types of passive income… more for my own peace of mind than anything (so I’m not solely tied to rise or fall of any single business). I explain more in this blog post (be sure to check out the video).

  4. Bryce Robbins says:

    Hey Seth,

    Another fantastic post! You have such a gift for explaining things in a clear and succinct manner. Thanks for continuing to share with this community and giving us some personal insight into your own story.

    Best of luck with everything, and glad to hear you are enjoying being JOB free 🙂


    1. Seth Williams says:

      Thanks Bryce – much appreciated! I appreciate the well wishes. 🙂

  5. Kenneth Anderson says:

    Congrats! I haven’t gotten to a point where I can walk away from the rat race. I have been looking at options, when I do decide to walk away. Just like you said, it is very scary to walk away from the comforts of your job. However, jobs are not really that secure. I have faith you will do well.


    1. Seth Williams says:

      Thanks Kenneth! Hang in there man – your day is coming. All good things come with time and patience. 🙂

  6. Bobby Wallace says:

    Hey Seth ~

    First, let me say “CONGRATULATIONS” for having the faith
    and courage to make one of the biggest decisions in your life!

    Great article! Wish that every Real Estate Investor’s Group in
    the country would make your outline required reading for
    newbies (wouldn’t be a bad idea either for the “veteran investors”
    who want to go “Full Time” and leave their day job. 🙂

    As a “Old Dude” that has been self-employed for many years, I agree
    with you 100%; the only thing that I didn’t see you mention is how
    lonely it can be if you do not have a couple of like-minded folks that
    you can bounce ideas off.

    I can remember several mornings when I would be getting ready to
    do something that was not work-related to my real estate business
    and I would hear my fax machine pick up…and a mastermind buddy
    would be faxing me a copy of a big closing check …and it would quickly
    motivate me and remind me that I was self-employed…and why I chose that

    Wish you continued success and blessings, my friend.

    I appreciate you,

    Bobby Wallace
    Charleston, SC

    1. Seth Williams says:

      Hi Bobby, thanks so much! I appreciate you sharing your thoughts about staying connected as a self-employed person too. It’s important to maintain those relationships that keep us motivated to do what we’re born to do.

      Thanks for the wisdom!

  7. Ryan Huggins says:

    Congratulations on making that jump! I did it as well a few years back and my only regret is that I didn’t do it sooner!

    1. Seth Williams says:

      Thanks Ryan! Great to hear from someone else who made the leap too!

  8. Rockroserealty says:

    glad to hear you are enjoying being JOB free. thanks for sharing such things with us…..

    1. Seth Williams says:

      Absolutely! Thanks!

  9. Gabe Sanders says:

    Seth, being your own boss is not for everyone, but when it works it can be a wonderful experience. (As long as you don’t get fired! 🙂 )

    1. Seth Williams says:

      Thanks Gabe! I agree – it’s definitely not a cookie-cutter solution for all, but it can work great for some people and situations. 🙂

  10. Thomas Kutzman says:

    Seth, thanks for sharing your experience in this post. In February 2016, I said goodbye to 12 years in the financial services industry in order to dedicate 100% of my time to build a new for sale by owner real estate platform http://www.prevuapp.com with my co-founder in New York. I receive a lot of questions from friends in finance about what it’s been like taking the entrepreneur / startup leap. I will make sure to bookmark your post to share with them when I have those types of dicussions. All the best, Thomas Kutzman

    1. Seth Williams says:

      Thanks for sharing Thomas! Best of luck to you in your new venture!

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