‘Gigging’ and Second Career Boomers: How a 2018 Entrepreneur Looks at Life

winslow-wifey at oroast
Oyster Roast is one of our Men’s Club special events. With Winslow & ‘wifey’.

Moving onward/adding another ‘gig’ has proceeded positively, and I am embracing to the max the 2018 embodiment of freelancing that’s always been a strong club in my personal creative bag. Having utilized verbal and written communications across all previous jobs, bringing those strengths to a Second Career notion we Boomers hold so dear is a legitimate attitude.

Similar vein, making a three chapter submission–  9200 words and tight– for my second book is less a milestone than an essential process.

There are numerous outlets-ways to monetize extra skills in current writing arena, in part because of people’s ability to telecommute with work product. I’ve been a reading-writing-public speaking tutor with Wyzant and Thumbtack for years, now I’ve hooked up with FlexJobs, Dice, The Creative Group and a couple others. I’m involved with a sports blogging function for the local NFL team,.  Economically I’ll be a resource, not an employee, the rest of my career. I didn’t have any problem prospecting in earlier careers like real estate, but in 2018 its sooo much easier to utilize the volume of pointed, quality, reliable leads possible from sites like FlexJobs than early 1980’s search in Tampa.

Having made Mom’s lunch, I’m available and dedicated to the process, BUT, it’s a fantastic 76 degrees of Carolina spring outside, and the temptation to really stress test my replacement knee with a 16-18 mile bike ride is probably going to be the deal. I have great faith and enthusiasm for that knee, re-adding athletic skills that got shelved the last half-dozen plus years is exciting. I have a preliminary date to whack a bucket of balls Saturday, and there’s a captains choice golf tournament at the end of April as a goal. I’m back up to my rugby weight (188) from 1986, been going to shoot hoops regularly, and *running* after misses is a joy, as is hoisting catch ‘n shoot jumpers from all over.

Mom has made great strides on mobility, too, we walked completely around the lake several times last week, and yesterdays stroll around the building was done fairly quick. Along with improved appetite and keeping her meds right with a dispenser 3x a day, that walking has improved her 84 year old knees to a great degree. We play ‘Kings in the Corner’ card game a lot, watch Dr. Phil, and yes, there’s a lot of psychic income knowing I’ve made a difference with walks, appointments, lunches, and health by being a good, helpful son.

That’s what being entrepreneurial looks like to me: I’m the brother in Charlotte with a job description that allows me to work wherever I am. Although Mom’s apartment at Carmel Hills doesn’t have wifi, I grin and bear that, and yes, I’d create a hot spot if really needed it. Carrying a sketch pad to journalize with is a long time habit, and I can be highly mobile any time of the day.  (Just FYI, cars name is Bullitt2– don’t get deep on politically correct, its more about Steve McQueen.)

mom-rummicub

‘Time’ is a primary factor for giggers, usually the ability to devote chunks to specific ‘other’ circumstances. From mid-December surgery until the beginning of March, I rehabbed hard, and being primary caregiver for my mother since she got out of hospital on Valentines Day was 35-40 hour commitment, down to twenty by July.  While that’s not a killer schedule by any means, gigging mitigates conflict—even if that means writing proposals or blogging after 11:00 SportsCenter.

Glenn S.

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