As a 15-month, bootstrapped start-up with one friends-and-family loan and no other outside funding, I hire freelancers per piece and per project to assist with the work of the company.
The “free” in freelance means just that - free to be allied with oneself, not with a company, free to say “yes” to work one likes, free to say “no” to work one doesn’t, free to work with a company for awhile, free to not work with it for awhile, ever, or ever again.
The “free” in freelance is an ideal match for my company’s enterprises, particularly for business news site Handshake 2.0. For Handshake 2.0, I seek excellent content, not good content. Excellent content is born of free creation from the heart and mind of a person’s deep expertise and talent.
On Handshake 2.0, we currently average at least one post per day. If 365 freelancers contributed from their hearts and minds only once per year, that’s a plethora of top quality content for Handshake 2.0. And that’s a lot of freelancers with a new publication to add to their publication lists and a new link to their sites. Oh, yes, and I pay. To the best of my ability, on the day I receive the invoice, I write the check.
A developing challenge for me as a company founder is that I’m finding fewer freelancers applying for freelance positions. I’m finding more people who need work turning to freelancing who then apply for a position.
Although I’ve been deeply fortunate to experience exceptions, for the most part, those who turn to freelance content creation do so because they have a skill, not because they have a passion for creation. As a result, they gamely create adequate to good content, not excellent content.
Do I see potential in them to create excellent content? Yes. Does my start-up company have the time or resources to employ, coach and support them while they learn? No. Can I ask them to reach more deeply into themselves and create more powerful, distinctive content? Not for the pay I offer. Someone who needs work needs to crank out a post, then look for more work.
In a down economy, a former employee turned freelancer is not free. Writing developed when domestication of plants and animals gave people time to think and create. While hunting and gathering, i.e. seeking the sustenance of a job? Hunger is not a free, or creative, state.
In a new, entrepreneurial enterprise, the company founder is not free. An established, domestic state is five years away. Now, I hunt and gather revenue intently to feed this newborn baby of a company.
A fine, local company closes its doors today, laying off all of its employees.
More freelancers.
To create real jobs in the future, not just freelance work in the present, as a company founder I must, day after day, create excellence.
I am deeply uneasy with the paradox of realizing that, in order to create excellence, I need to offer work to those who want to create, not to those who need work.
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Photo credit: Jennifer Greger




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