Here's to All of You Who Make Work, Income, and a Path for Yourselves...

Updated: Oct 15


Photo by William Perugini (123rf.com).


...and my favorite sentence ever read in Forbes.


Apartment rentals. Auto detailing. Auto repair. Bartending. Bookkeeping. Calligraphy. Computer classes for seniors. Computer/internet repair and set-up. Custom-baked birthday, wedding, and special-occasion cakes. Custom-built decks and garages. Custom-built guitars. Custom candle-making. Custom concrete work for patios and sidewalks. Custom-created drapery, awnings, tents, and camper attachments. Custom-sewn bridesmaid, wedding, and first communion dresses. Delivery. Driving. Electrical work. Furnace repair. Hauling. Housecleaning. Homebuilding. Home repairs. In-home childcare. Interfacing with contractors for seniors. Lawn care. Mending. Moving. Nannying. Painting. Personal training. Portrait and wedding photography. Powerwashing buildings, decks, buses, and boats. Quickbooks help. Real estate investment. Record store owner. Refrigeration. Renting catering supplies. Reupholstering. Roofing. Salvage work (junking!). Selling one’s paintings. Siding installation. Snow removal. Special education tutoring. Tavern owner. Tent repair. Used furniture buying and selling. Wedding catering and dessert spreads. Wedding invitations. Weekend rock star. Window and door installation.

I could develop a whole sub-genre raining kudos on all those who make work, money, and a path for themselves, part-time or full-time, starting with those in my family (mom, dad, grandparents, sisters, brother, brothers-in-law, aunts, uncles, and first cousins) who I’ve seen from my earliest years do the work listed above as free agents, independent contractors, and small business owners. [Note: Big family. My mom’s from a family of 7 kids, my dad’s from a family of 15 kids, and I have about 60 first cousins.]

A special call out to my maternal grandpa, Leo, who in his 70s, 80s, and 90s helped finance the first businesses of many of us in the next generation, including mine. He left his work as a roofer to learn the heating and refrigeration business. Among many other things, he went on to install the first beer coolers in every bowling alley on Chicago’s North Side. On one job he fell into a vat of sauerkraut, but that’s another story.

They determined what they wanted, took responsibility, employed creativity and conscientious work, and enjoyed the freedoms, satisfactions, and income from that. They served and delighted others at fair prices, and often made work for others and stronger communities along the way: human to human — without most of the bureaucracy, BS, and soul-crushing that goes along with so many workplaces.

They inspired my own path. My only paychecks in life came from McDonald’s (age 16), Don’s Garden Center (age 17), work study jobs in college (which I left ASAP as I could make more money on my own than the minimum wage they offered), miscellaneous restaurants and temp jobs in my early 20s after graduating from college with a philosophy degree, and a recent 11-month stint in scholarly and professional publishing (my only steady “adult” paycheck — cool, but meh). My 35+ years of experience with self-employment started at 16 with math tutoring, which became my primary source of support until I started my first book publishing company at 25. In three-plus decades, I learned a lot about life making my own way in these ways…

Algebra teacher for gifted students. Banquet hall server. Bartender. Book publisher. Coach. Corporate librarian. Custom book developer. Ecommerce retailer. Editor. Event planner. Freelance writer. House cleaner. Math tutor. Mover. Print broker. Project manager. Publishing consultant. Researcher. Small business consultant. Speaker. Tradeshow worker. Workshop presenter.

Perhaps nothing inspires me more than people who decide not to wait for what they want but to create it instead — however they can, from wherever they are. It is a beautiful blend of realism and idealism that makes my world go round. And I see it all around me every day in the real world and online as I read about the new ways people are cobbling together gigs, contract work, side hustles, passive income streams, and creative work to make a living and a life that works for them.


I see you. It makes my heart hum, and I have been cheering for you a long time:

  • Anyone and everyone who has, is starting, or wants to start a 1–5-person business or a ramped-up solo assemblage of products, services, and income streams…If you do it part-time, full-time, casually, or seriously…


  • If you think it’s your route to taking control of your life…


  • If you bring your kids with you to collect pallets or deliver newspapers on the w weekends for extra spending money…


  • If you suspect taking responsibility for your day-to-day work is going to increase your happiness…


  • If you want to tap the self-determination and creativity that started and fuels your business to bring you greater personal and financial rewards…



  • If your small firm is running smoothly and it’s time to add the polish or think about the rest of your life…


  • If you have the most excellent idea that a side business is a terrific hedge against possible unemployment (defensive entrepreneurship)…


  • If you’re a stay-at-home parent with pockets of time mashed into your crazy schedule…


  • If you have an established business but it’s doing more for your employees and your customers than it’s doing for you and it's time to change that…


  • If you’re a freelancer, consultant, or solo professional that wants to scale up your business…


  • If you’re hitting midlife and thinking you need a big change in this “small” direction…


  • If your small operation is always struggling to stay in the game…


  • If you are down on your luck, starting to panic, and don’t know where to begin, but you're ready to do what it takes…


  • If you have the brilliant notion that self-employment may be a major self-development experience, akin to a committed relationship or raising children…


  • If you're a soloist, solo-pro, solopreneur and have real skills and want to make real income on your own terms…


  • If you’ve ever attended a pink slip party, boo-hooing in your martini because you were entitled to that overpriced $90K job… (Hee. Hee. I throw this one in because I attended one such swank event in Chicago in 2001 as an outsider.)


I have been observing and championing you my entire life. For at least 20 of my 35 years as a small business owner, I spent up to half my time advising the leaders of small and solo enterprises — hundreds one-on-one and thousands through speaking engagements and workshops — and mostly for free. Until that lucky day I realized that I had discovered that thing I loved so much I would do it for free. I was doing it for free and it was at the expense of my business! (That conk to the head was the beginning of me becoming a coach.)



My Favorite Sentence Ever Read in Forbes

Elaine Pofeldt, a Forbes blogger who writes about one-person businesses, wrote the best sentence I ever recall reading in Forbes in her 2015 post “Who’s Afraid of the Freelance Economy?”.

In it, she takes on an earlier post by Robert Reich, Secretary of Labor in the Clinton administration and no slouch himself when it comes out to looking after the little guy. Reich’s piece “The ‘iEverything’ and the Redistributional Imperative” states that one problem with one-person businesses is that they don’t create employment and, among other things, it’s a sign that the future requires future workers and, thus, a new — and redistributional — economic model.

Pofeldt tells us that similarly, federal officials call one-person businesses “nonemployer” businesses.

So, here’s the sentence:

“What few pundits seem to notice is that these solo entrepreneurs have created 22.7 million jobs — for themselves.”

My hero!

She goes on to add, oh by the way, that they have created these jobs for themselves with “little support or encouragement from the government.” No incentives, handouts, bailouts. On their own, with their own bootstraps (I’ve written on this particular irony in Values Arbitrage).

And then, “They are seen as too small to have any intrinsic value…” Right! 22.7 million and growing (the number has increased almost 30% in the last decade). 22.7 million individuals unaffiliated with unions or corporations and still making a living.

During the too-big-to-fail bailouts and extended unemployment benefits of 2008+, all I could wonder was: What if that money were distributed to small businesses to hire one more person each — wouldn’t the economy be thriving in a different way? A bit of power redistributed as well? I will be interested to see what the eventual research will show on the effect of the range of cash payouts to individuals and small businesses in 2020 and 2021 on the economy at large, small business growth, personal satisfaction.


Too small to have any intrinsic value? Or, small enough to succeed better?


Stick around! This website and Conspire Creative are for you. We're living through precarious and interesting times, and customized routes to work/life success may be the best option for many of us to meet the moment.