Day Jobs, Self-Employed Entrepreneurs, and Street Cred

For years, I lived the life I had dreamt of: living on my own terms (in a way. You know, “my own terms + husbands thoughts + pet and home responsibilities” doesn’t sound as sexy) and making my own way as a self-employed entrepreneur. I felt like I had made a goal that so many aspire to reach. I had damned The Man, hustled all day erry day, and so on. I felt I was walking walks, talking talks, and living the way I felt I worked best.

However, money was always in flux because my income was based on freelance work, I worked ridiculous hours, and I never felt satisfied. I was successful in one way and unsuccessful in my own head because I wasn’t successful “enough.” No matter my recognitions or scale ups or goals reached, it wasn’t the right feeling. I felt like a fraud, like I had no real entrepreneur street cred.

In 2015, when we decided to leave Brooklyn, I too decided that I wanted to re-enter the office workforce. I knew my talents would be put to good use, where I could provide for my family better than I could staying fully self-employed, and it would be a great feeling to have someone else have to worry about “it” every night, you know what I mean? But going back to working for someone else…that meant I wasn’t full-time self-employed. It meant, in my head, that I had no entrepreneur street cred.

You see what I’m getting at here? There is such a vulnerability someone who works for themselves has, this feeling of restlessness and insecurity. The entrepreneurs I’ve met, whether they’re full-time day jobbers, part-time self-employeders, or full-time self-employed, all feel this way. Like it’s never enough. Like you’ll be found out.

I’ve been thinking about this a lot since I found out I’d be speaking about marketing at Alt. this upcoming March. I’m the Head of Marketing in a company because I intentionally chose to leave full-time entrepreneurship; does that mean I have less entrepreneur street cred because I’m not out doing my own thing? What if no one wants to hear what I have to say because I get up and go into an office?

And you know, it’s all ridiculous. As I’ve told my therapist (shout out to Brian!), I know two things in my life to be true: my marriage is strong and I’m good at my job (the rest of my life? No fucking clue.). But there will always be that part in my head….that “what if?” part. And you might have it, too. You might think you’re not really hustling, you’re not a girl boss/boss bitch/lady boss because you’re not a millionaire, or your Instagram following isn’t high “enough”, or you have a day job.

As someone who has been on both sides let me say: you’re a goddamn baller. Whether you’re just thinking about a business idea, doing it after work and on weekends, you’re doing it all on your own, or you’re doing it with a staff and an office, the “street cred” has been attained. Your life is your life and creating benchmarks against someone elses ideas is a perfect way to feel inept because no one else has your life. Sure, they’ve got aspects of it, but no one else is the complete package.

So yes, I’ll be speaking about marketing at a conference in 2019, and I know that one or two (or a dozen, or dozens) will feel my street cred as an entrepreneur isn’t there anymore…and that’s fine. My life is on my terms, and yours should be, too. Rock your street cred, because I know you’ve got it (even if you don’t think you do).

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