I always told my daughters that the way to find happiness is to find your passion and then find some way to get someone else to pay you to pursue it. You will never feel like you worked a day in your life since it's so much fun to go to work. In retiremen for you. What do you LEGALLY to help offset the expenses of the lifestyle you love.
I agree 100%
I retired from working full time in 1992 when I sold my video stores. I was 41. I have not had a full time business or job since and started taking July to September off around 2003.
My first careers after college was in law enforcement and retail security/loss prevention. Then I was a retail executive until opening a video store in 1983.
I became a Nobeltec dealer selling VNS shortly after selling the store. Back then, older boaters were buying their first computer in order to run Nobeltec and I installed the software and offered training to use it. Received free software, training, wrote off laptop, GPS, mileage, phone.
Got a Coast Guard 50 ton license and began offering on the water Nobeltec training. Wrote off Maritime Academy tuition, books, milage and license fees. This led to working part time for a yacht time share company in Seattle as a contract (1099) checkout skipper. Wrote off mileage, tools. Which led to managing several boats in the fleet for maintenance. Which led to being a boat handling instructor for the time share company when they started Yacht School. Which led to working as a skipper for hire when the time share company started that. Was able to drive all the 180 plus boats in the fleet and clients to gain experience with different boats and accumulate sea time on boats larger than mine. Received training on various boat systems and equipment and started relationships with marine equipment dealers and manufacturers.
About the same time began becoming a dealer for a variety of marine equipment manufacturers. Sealand, Webasto, Westerbeke, Furuno, American Diesel, FloScan, Robertson etc. Benefits were equipment purchase at wholesale prices, free training, write off home office, truck expense and depreciation, computer.
Quit the time share job and started my own "On the Water" boat handling instruction business around 1995. Wrote off books, charts, milage. Which led to consulting to new boaters on choosing, how to buy, equip and handle a boat. I was not a broker. Also hired out as a skipper for hire doing deliveries and backing up captains on large yachts. Worked the license up to 100 ton. Retired that business in 2014.
Started buying marine equipment at swap meets, garage sales, Craig's List and selling on eBay. Which led to selling at marine swap meets that let me arrive early to set up which allowed me buy the good stuff prior to the start of the event. Wrote of booth fee, mileage, home office. Get to try out marine equipment that I might keep or sell.
I also had several other part time businesses simultaneously in addition to the marine field:
I started a mystery shopping consulting business where I sent people into businesses to pose as shoppers and assess customer service. We shopped banks, hardware, department and mattress stores. Wrote off vehicle mileage, phone, computer. Retired that business in 2004.
I had started a part time mobile DJ business in 1974 and was doing two to four gigs per year until 1992. After selling the video stores, started to aggressively advertise the DJ service and by the late 90's was doing 40 to 60 events per year. Got to purchase all the albums and CD's that I wanted without checking with my wife. And purchase the latest and greatest pro audio gear as the technology advanced from singles, albums, tape recording, CD's, Mini Discs, recordable CDR's to digital music on hardrives. Wrote off music, computer, audio equipment, stage clothing and mileage. Retired that business in 2017 after 43 part time years!
With all the part time businesses running at the same time, I had several Schedule C's on the federal taxes. Expenses like home office, CPA, office supplies, vehicle expenses, attorney and depreciation were prorated into the various Schedule C's. I had a dedicated laptop for each business and several phones. I had profit from the businesses and paid state and federal taxes. None were "hobby businesses".
The businesses were LLC's for personal asset protection and I carried liability and Errors & Ommission insurance.
I still sell new marine equipment to clients, but no installation, and sell new and used items on eBay. And pay tax on profit.
Out of all the businesses above, I made the most money (gross) on boat handling training, mystery shopping second and DJ'ing third. EBay sales is the most profitable (net income) and DJ'ing was second.
Working as a DJ was my favorite business and the most fun. I catered to the yacht clubs and country clubs around the PNW, which led to referrals from high end clients and elaborate weddings. I also worked corporate events, private parties and had several corporate clients for over 20 years. I never had to work a kids party or school function - no teen music! Received tips in addition to my fee and one was a $350 tip at a wedding reception!
I would have continued working as a DJ into my 70's if it wasn't for smart phones. When someone made a request for an undanceable, inappropriate or a song I didn't want to play in the old days, I would simply say I didn't have it. After smart phones became popular, when I said I didn't have a song, a guest would hand me their phone and ask me to play it. Many songs have objectionable lyrics and I only played clean versions. It's not that I am a prude. I didn't want someone at a party to be offended by the lyrics and there are always children at wedding receptions. And every event was a referral opportunity.
Starting businesses in areas of my interest and hobbies has been very rewarding- financially and personally. And I recommend it to everyone.