Shake Logo

“Design Your Own Career” — Advice from a Successful Entrepreneur

by Dakota Kim

“Design Your Own Career” — Advice from a Successful Entrepreneur

Jen Dziura is the founder and publisher of Bullish, a popular site that offers innovative career advice geared towards women. We talked with her recently about pursuing an unconventional career path.

Should would-be entrepreneurs leave their jobs to pursue their passion projects, especially in this economic climate?

Throughout my career I’ve been very risk-tolerant. But that doesn’t mean everyone should put all their eggs in one basket. If you’re a struggling freelancer, it’s possible you’re simply in an oversaturated field. It’s really important that freelancers diversify or be willing to change careers.

What I would say about trying to turn your skill or passion into something more financially sustainable is take whatever you do and mix it with something else that people find scary or boring.

What I would say about trying to turn your skill or passion into something more financially sustainable is take whatever you do and mix it with something else that people find scary or boring. Stand up comedy mixed with educational speaking or other stuff is much more marketable than stand up comedy alone. Everyone wants their corporate training to have stand up comedy. You’re going to have a much more sustainable business model. When I talk about taking risks, I don’t mean digging a deeper hole.

What would be your ideal working world?

Over the last few decades, women have pushed for more flexibility in the workplace. I’d like to see a working environment in which people are not stigmatized for deciding to work less and where they are rewarded for their productivity regardless of the hours they choose to put in.

One of the big problems I have with “Lean In” and the culture around it is excessive corporatism. We live in a country where corporations are now legally people, and we don’t need to give up the better part of our lives to huge corporations.

I’ve always been writing from a contrarian position of designing your own career. A big corporation won’t look out for you or have a career path for you. I also found it to be really joyless, giving yourself over to a corporation. I have a large audience of people who want to be ambitious but without giving into that.

Is it important for you to have contracts with all the people you work with?

Sometimes it’s helpful to have a contract just so everyone understands the obligations. Some types of agreements don’t do a whole lot for you until you’re willing to sue. Since most freelancers are not in a position to sue, sometimes there is no enforcement for contracts. I suggest that those freelancers get a book on small claims court. You can find out how to send a letter saying how you’re going to begin suing someone.

You want to look at contracts as a way to formalize and clarify a business relationship. I have an example. A friend invested in a business with his friend. They’ve been friends for a million years and they didn’t think they needed a contract. The friend’s father is a lawyer and made them do a contract. While they agreed on most things, they didn’t agree on what happens when one of them dies. It’s the sort of thing you’re forced to think about when you make a contract.

Once you use Shake, it really brings home the ridiculousness of what a lot of people are doing, which is scanning and emailing contracts. Being able to actually generate the contract and sign it all in one place is pretty great.

What’s next for you?

I’m writing a book. It’s actually very challenging. Having spent so long running little businesses, I find it a lot easier to start a company than write a book. It’s going to be a Bullish book – aggressive advice for young women.

Dakota Kim is a freelance journalist covering the arts, style, business, food and travel. Her work has appeared in SalonThe Huffington PostBedford + BoweryThe Wall Street Transcript, and various in-flight magazines. Tweet her at @dakotakim1.