How to Create The Best Job You’ll Ever Have

a frank Interview with Elizabeth Osder

Elizabeth Osder, the first girl to play in competitive Little League Baseball.

Elizabeth Osder, the first girl to play in competitive Little League Baseball.

This is the first time we’ve had a record breaker among our FRANK women: Elizabeth Osder, who was the first girl to play in competitive Little League Baseball! From an early age, Osder was doing things her way. A close friend and advisor, she’s one of the people who I’m lucky to be able to call when I have career-related questions. Here, she shares her best advice on how to create your own opportunities, when you should negotiate a salary, and more.

As a practitioner of creating your own opportunities, how do you go about it? Do you think this is something that everyone can do?

I think that everyone creates their own opportunities; a career is your own canvas, no one can really fully paint it for you. But we all have styles. I would say that I have been improvisational, and have followed my own advice: “the best jobs are the ones we make and not take.” I have had a lot of jobs and most came with loose job descriptions and the mandate to figure something new out – there were metrics and goals, but usually a lot of open space. I don’t paint in the lines and therefore these were the best opportunities for me, and when someone had a strict criterion for me, I was more likely to not be successful. Call it bucking authority, or being a pain in the neck, it's just not easy for me to do the same thing repeatedly. I like to look at things from different angles and this is not a good fit for lots of kinds of work.

The key to making opportunities is to be open to them, to pay it forward, and to offer to help and share before strictly trying to make a deal. I have a lot of experience, tradecraft, and knowledge about digital media and that experience is easy to share. Sharing builds relationships, and when the time is right, often the gig will come. I have been very lucky, had great mentors and serendipity.

What are some lessons you wish you'd learned earlier in your career?

I am not sure I could have learned them earlier. We learn to stop making the same mistakes over and over again as we mature. Key lessons for me, and ones that I think others could benefit from:

  1. Be a better listener, even when your mind moves quickly and you might get impatient.  

  2. Stop and think about what you are about to say, do, and how it might impact others, your work culture or the project. I am intense and tend to focus on the task at hand so intensely that I forget that others may need more time, training, or explanation.

  3. Even when it might not be in your job description or even directly related to your field, get a better handle on financial analysis. It will help you make smarter choices.

Do you think one should always negotiate a higher salary? Any tips on how to go about it?

Ideally yes, you gain more experience, you have more value and you should unlock that value as your career evolves.

However looking back over my career, I think of salary as a game of chutes and ladders – sometimes you hit a few ladders and your income grows and grows and other times you hit a chute, and it drops below. When you have been around as long as I have, you recognize that there are real macro-economic and political reasons, and also personal ones. It took me many years to get back to my salary before 9/11. I chose some different paths along the way, being a professor and pivoting from consulting to product development and from full-time employment to consulting. I have lost jobs I have wanted by asking for too much and resented jobs I have had for thinking I was getting too little. The mind, ego, and your sense of value can be complex.

On negotiation, you should think about the total compensation package. Know what you are worth, be proud and confident asking for it, but don’t let money get in the way of pursuing jobs that will provide you training, knowledge, and experience that will essentially give you “equity” for all your future jobs.

Do you find what you do fulfilling?

I have loved my work, because I have a simple goal in life, teach and learn something new each day. We spend about one third of every day working. If I had done all this just for money it wouldn’t have been worth it, but I have gotten so much more...and it keeps giving, with knowledge, friends, travel, great stories, and perspective.

Luz PlazaCareer Change