I Have An Axe to Grind

Alexandra Ostrow
5 min readApr 10, 2014

Recently, I attended an event on breaking barriers to women’s empowerment. After listening to speakers, who had flown in from all over the world to discuss the importance of supporting one another, I found myself discussing gender parity with a few of the other attendees. Or at least, that was the topic of conversation until it shifted to our occupations:

I’m a freelancer.

The responses I received were varied, but not at all unusual: “Oh… So, what’s your next move?” “How’d you get an invite here?” “Are you a journalist?” and “You’re so lucky you don’t have to work for someone.

In a culture that revolves around a 9-5 schedule, the term “freelancer” holds a great deal of negative stigma, and an equal amount of mystique. Temporary career setback? Lacking in drive or value? Pursuit of creative outlet? Autonomous income generation?

For several years, I kept myself gainfully employed in salaried positions with health insurance and a 401k. I worked long hours, built wonderful relationships with clients, and focused on job title promotions that enabled greater long-term growth.

In spite of exciting accounts and promising promotions, I didn’t feel satisfied. The only goal that motivated me was the goal of going out on my own. I resented having to report to the same location every day of the week, had little interest in performing the same daily tasks for clients whose values didn’t align with my own. I wanted the freedom to choose my projects, to learn and apply new skill-sets, and to walk through the park in the middle of the afternoon without someone questioning my whereabouts.

So last May, I did it. I went out on my own. And I’ve spent the last ten months working to hone in on my ideal job description. Some personal requirements?

  • Build digital strategies to advance the voices, missions, and products of those who aspire to better our world
  • Engage in respectful & collaborative working relationships to fulfill my responsibilities while mutually honoring personal priorities
  • Maintain the freedom to take a month-long commitment overseas… or to work from my couch flanked on either side by my dogs and my cats

To battle the stigma of the “freelancer” job title, I experimented with calling myself a consultant, but here’s the thing… I’m a freelance consultant. Above all else, I maintain my freedom. And so do those who hire me. I pride myself on offering a mutually beneficial arrangement. I’m an efficient and diligent worker. I bring a broad range of experience to every job, and I’m also eager to learn. I come with little to no overhead, and I’m fair in my budgets. Plus, I’m a short-term investment— with no need or desire for a long-term obligation.

Lest you think I’m viewing the freelance experience with rose-colored glasses, let me share with you some of my challenges. It’s lonely at times, finances can be unpredictable, health insurance is expensive, and the NYC rental market does not look kindly on the term, “self-employed”. Also, there’s no manager giving direction or feedback, and I’ve been to one too many networking events where someone has responded to my job title by questioning whether I plan on getting a “real job” soon…

Even with these challenges, I choose to refrain from signing a long-term contract that ties 40+ hours/week to a recognizable logo, just to afford myself societal legitimacy. These are challenges I’ve chosen to embrace. And what’s more, I don’t consider them to be reckless or irresponsible. My risks are just a bit more obvious than the risks surrounding a corporate job.

When you take a moment to look below the surface at most full-time jobs, they are not, in fact, “secure”. If I told you to go online, find someone that looks attractive, go on a couple dates (four at the very most), and then commit yourself to spending the next two years by their side, would you? For most, this is the hiring process. A recruiter reaches out (or you send a cover letter), and it’s usually two, three, maaaybe four interviews before you’re hired full-time. From there, you commit yourself to spending 8-12 hours/day for the next 1-2 years minimum, and you haven’t yet seen them naked. You have little clue of their political views, subscriptions to religious doctrine, sense of moral values, or prioritization of family life. You don’t have access to company-wide financials, can’t assess quality control, and management could, on any given day, carry out layoffs. You pay a percentage into the potentially useless healthcare plan they assign you, invest hard-earned dollars into a designated, and potentially precarious, 401k. And then, you stay there—even if you’re unhappy.

My intention is not to demonize full-time jobs, but to merely pull aside the curtain. We don’t become freelancers because we’re unreliable, noncommittal, or lacking in full-time opportunities. The freelancers I know are courageous. They can’t define their self-worth by a recognizable company name. They won’t slack off because they’re building their own business. They’re forced to evaluate their personal client criteria, while navigating parameters for quality of life and simultaneously balancing their checkbook. They wake up every day because they, on their own, thought that this was the hour they should get up. They share the risks of an entrepreneur, but without being glorified by news sites and media.

Shall I go one step further and share my fears with you?

I’m frightened to publish this post. In my head, there exists the possibility that I will lose out on future opportunities because of my open dismissal of corporate structure… After all, my clients are established businesses and nonprofit organizations. But then I remind myself that what I’m doing isn’t always easy. I took this path because I wasn’t happy in corporate culture, and I was no longer invested in the clients I had.

I stand for something. I stand for a world where we are able to change things, where we can create a culture that is more accepting of those who deviate from the norm, where we question the status quo in an attempt to make the world better as well as to make ourselves happier. I look to my right and I see a snoring dog sleeping content on the couch beside me, and I remember that my clients respect this, even if my cause is different than their own. They too see things they want to change in the world, and my services address their needs. So I take a deep breath and re-focus my attention back to my work. Maybe I’ll take a walk through the park today.

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Alexandra Ostrow

Strategist & Marketer for Social Impact & Innovation | Founder of @whywhisperco | NYC Native | Loves Food & Travel | Smiles at Strangers | www.whywhisper.co