Freedom Is Just Another Word For Being Your Own Boss

Updated: Apr 29

Is It Time To Change Tracks?


It is true what they say: Your worst day self employed is better than your best day working for someone else. Whether you’re out of work or you just hate your job keep reading. I’m going to tell you how my wife and I reinvented ourselves twice. The first time we started a 20 year retail business as a side hustle. The second time we built a successful business with only $20 and retired early after 7 years.


I was a software engineer for the government. I was also an avid golfer and had a curated classic and antique golf club collection. I was always buying bags of clubs at yard sales and flea markets that had a collectible wedge, putter or driver in it that I wanted to add to the collection. We had to put an addition on our house to display the collection and another to store all of the extraneous sets of clubs that were fine clubs for the most part but just too new to be collectible.

I finally put an ad in the local paper that just said “Golf Clubs For Sale” and a phone number. Maybe once a week I’d get a call and a prospective buyer would come by to see whether I had anything they wanted. One day I got a letter from the president of our homeowners association stating that selling anything out our home was a violation of the HOA bylaws. This HOA president was also the president of our golf club which operated the only golf pro-shop in our area.

Well, now I had to find another outlet for dozens of sets, odd clubs and bags. It just happened that less than a mile away there was a small strip mall with a 600 sq ft space available for rent for $250 a month. I opened wholesale accounts with Golfsmith, McGregor Golf, Dexter Shoes, J&M Golf Supply. and opened a real nice albeit small golf shop with a small repair area. I hired a very nice retiree who loved golf to man it 5 days a week for a percentage of the net. He was still with me 4 years later in our new 1,200 sqft downtown store. Oh, and the proshop at the golf course had dropped their golf club inventory.

I quit my GS-12 step 8 civil service job and moved the golf operation to a well located 1,500 sqft location in Florida where you want to be if you’re in the golf business. Four years later we moved down the road and across from the mall to a 6,380 sqft location and stayed there for 15 years. If you’re patient and only expand on demand you can make something out of nearly nothing with a very modest investment. The next story is even better.


In early 2008 my wife and I were both pretty burned out in our current carreers. She was a real estate broker in a market that was in turmoil due to the bank lending scandal. I had the golf store which had experienced a marathon 6 lane road widening project for nearly 4 years. It seemed like the right time to go while it was still on our terms. We had a second home in the mountains that we had visited nearly every month for the last 3 years. The stays at the cabin got longer each time we went and we finally decided that we’d rather live there than just visit.

Once the decision had been made we had to close the businesses, liquidate everything of value and buy vehicles compatible with 4 season living in the mountains. That finally done, we hit the road one last time for the nine hour drive to the cabin. We didn’t have a plan for our future. We just knew where we wanted it to be.

I think I thought we had retired because for several months we spent our time shopping, gardening, shopping, decorating, shopping, weatherizing, shopping, golfing, shopping, entertaining, shopping, relaxing on the back porch gazing at the view and of course, shopping. As much fun as that sounds it couldn’t be maintained forever and I could see the writing gradually being revealed on the preverbial wall and it said “you’re poor”.

So, there it was, reality was showing its pointy little head. What should I… we do? I loved the idea of another store but knew for sure I didn’t want the hassles of an inventory again and neither of us wanted the stress of a large initial investment, rent and utilities overhead in a startup. So it had to be a service based business. But what can we do? My wife is brilliant and I’m a thoughtful bloke so after some consideration we decided on an unlikely but almost risk free path forward. We were going to be a husband & wife handyman team.

But first there was some basic learin’ to be done so I went to work at our local Hardware store for 6 months where I received a crash “on the job” course in practically everything one had to know before embarking on such a multifaceted career as a handyman. Looking back I still didn’t have a freaking clue what we were getting ourselves into. Good thing too or I probably wouldn’t have attempted it. Ignorance can be bliss.

I had a couple hats and tee shirts printed and put a $20 ad in our local paper containing claims of all sorts of researched yet untested skills. I’ll be damned if the calls didn’t start coming in! Thanks to the internet, common sense and lots of luck we got through those early months replacing water heaters, toilets, faucet repairs/replacements and other light electrical and plumbing jobs without serious mishap. The jobs were short in duration but plentiful enough to pay our bills so our dwindling savings were spared. Let me be clear though, we paid our dues with a lot of tedious and backbreaking jobs. We weed whacked rocky hilly yards (fields actually) for hours upon hours at $10hr and cleaned filthy cabins for rental companies where, after buying cleaning supplies we made only $3.50hr.

I changed our business name to something more credible sounding and created a GoDaddy website, subscribed to Angies List and Houzz, put the website on and every other online guide I could find when I searched for handyman services and I put all our past customer’s testimonials on it so that prospective customers could check us out before interviewing us.

Then a few months later it happened. We got a call not unlike the others but it was the opportunity we hadn’t even considered. A couple from Florida needed someone to remodel their brand new log cabin vacation home’s unfinished basement. It was 1,200 sqft of nothing but cement floors and poured walls, 1 outlet, 4 light bulbs and an incorrectly stubbed out tub and toilet. They wanted a bath with a tile-in shower, a bedroom, storage closet and huge family room, all clad in tongue and groove pine including the ceiling. Outside they wanted a deck and a hot tub. The circumstances were perfect. The owners wouldn’t be there and they wanted to pay in 3 installments. We talked with them for a couple hours. Then we went home to prepare an estimate. That was a wakeup call too. So many details and items to figure into it. The logistics alone were mind-boggling! One missed or incorrectly performed step and the budget and timeline would be worthless. Two things my Pappy used to say came in handy. 1st is “You can’t make a living on a large volume of small losses” and 2nd is “What’s the worst thing you can do here?”. So I didn’t leave anything off my estimate. I accounted for every nail, screw, shim as well as potentials like delivery charges, dumpster and sub contractors if needed. I found materials estimating software specific to home construction and time and cost estimating software so my estimate was extremely detailed and professional looking. My wife and I were billed as a team for only $20 per hour at that time so there’s that and our estimate really impressed them so we got the job but not for the reasons I just gave. They said that we were their first choice unless we totally dropped the ball on the estimate. They said that their initial impression of those that came before us was dismal. We looked them in the eye, spoke in complete sentences, showed up on time and didn’t do, say or give the impression with our estimate that we were padding our costs in any way. They had confidence in us even though our experience was lacking for a project of that scope. We were over budget some but that’s because they changed the scope with the addition of the outside deck and hot tub. We hired a plumber to bust up the cement floor and reroute the rigid pipe and an electrician to wire the hot tub but except for that we did all the plumbing, electrical, tile and carpentry ourselves. The basement came out beautiful and we never looked back.

Our Angies list and Houzz references flourished and we won Houzz awards every year to post on our website. I also added “Kitchen’s, Baths & Basements” prominently on the website with photos of our work. Our newspaper add was constant and top left now in the classifieds. We were now targeting the vacation home market exclusively and got jobs from all our own marketing plus referrals from the HVAC, plumbing and electrical contractors we had hired.

I still bid jobs on a cost-plus basis (hourly plus materials) even after we had a team working for us. I justified it by explaining that when you bid by the job you have to pad the bid with every eventuality so even if everything went according to plan the customer still payed for every eventuality.

Our “Truth in bidding” policy page below explained the importance of trust between customer and contractor and that “It Is What It Is” meaning that it takes as long as it takes to do it right. If the contractor provides a detailed estimate, a daily summary of work and photos of same there shouldn’t be any distrust issues. Contractors that get paid by the job usually have just one incentive which is to get to the next job as fast as they can. Their bottom line depends on it. Our incentive was only to do a great job and create a loyal and satisfied customer base. We did that in spades. We routinely had clients that waited for us over a year. We couldn’t give accurate start dates because our current job was our focus and the scope of work expanded on most jobs. Prospective customers could appreciate that and counted on those same priorities when we got to their project.

We did 26 kitchens, baths and basements over the next 3 years and retired at 62. Four years later we got a call from one of our HVAC contractors saying he had just bid a job at a big cabin and wanted to know if we would come out of retirement before he recommended us for the basement renovation at the same home. I told him to go ahead and we would decide after talking with the homeowners. Very soon after that we got a call for a meet & greet at the cabin. It was a massive 3 story cabin with a blank slate 1,200 sqft basement like the first basement we ever did except this one wasn’t even stubbed out for a bathroom. The new owners were great folks and gave us almost cart blanche to design and build a rustic storage closet, bedroom, full bath, custom quad bunk area and great room with wet bar and a tin ceiling throughout. Our website was no longer online, we told them we hadn’t worked for the last 4 years, that we had sold our work van and a lot of our tools and my hair was below my shoulders. I wouldn’t have hired us but they did. The HVAC contractor’s referal and our honesty was enough for them. Four months later we left them a house that they sold a year later for a $250,000 profit and they called me to credit our work for making that possible.


I hope our story gives just one person the confidence and incentive to take a chance on a new self-employed career. The principles that helped make us successful will work for almost any new venture and assist almost any current enterprise. Entrepreneurial ship is too scary for most people but when you do it the right way it’s easy to shine amongst the local-yokel competition.

Without a doubt the most important things that contributed most to our success were listening, communication, honesty and promptness.

On a personal level don’t be afraid to fail, go all in and remember that your job is to make the clients vision a reality so leave pride behind you. The customer (and your wife) is always right.

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