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  • Seth Williams

Six Months After Quitting My Job – Here Are My Honest Thoughts

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 some day? How would I ever 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 thingand 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 could accomplish.

About 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

Freedom: 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 that this increase would happen, given the additional time I’d have to spend on my business, but I was also a bit nervous and skeptical about how things would pan out because as the sole bread winner 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 I always know this unpleasant task is coming again soon), it has helped me to plan and budget out the “pain”.

As an employee who collected a paycheck for so many years, my taxes were automatically withheld from each pay check and 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 much harder to overlook 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 fewunfortunate aspects of a concentrated land portfolio is that tax breaks don’t typically 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 didn’t spend 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 time to figure out how much money I’d have to earn per day in order to match the income from my steady, predictable pay check. 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 even with the passive income my business generates, no business ever earns an EXACT, predictable 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 problems. I 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 aren’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 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.


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