Getting the Career You Want, Part 3: Do it yourself (and maybe fail)

Failing is good for you. It doesn’t feel that way. It feels like a piano dropping on your head, or having your heart ripped out, which makes sense. Failure comes from a Latin word, fallere, that literally means to fall. But that—the pain of the fall—is also a mirage, a trick, which also makes sense. The same Latin word figuratively means to deceive. The pain, as much as it hurts, hides the lesson. The hard part is getting past the pain to find it.

The harder part is giving yourself the chance to fail at all.


Job searching has been a waiting game. And while patience may be a virtue, but it is not one of mine. When I hit my six-month mark of job searching last week, it was safe to say that I was tired of waiting for HR managers to get back to me. I was tired of waiting for that job that is a career: that golden job that has passion, purpose, and a paycheck rolled into one. My happy job was not appearing.

Then last week while reading in bed, I had a moment. It was one of those light bulb moments. I was reading the end of Barbara and Shannon Kelley’s book Undecided.1 The chapter I was reading discussed the struggles of single parents, having to work all day and come home to a second, full-time, unpaid job: homemaker. It’s hard enough for a household with two parents to work and come home and take care of the house and family, let alone having a single person do it all. As I read, I was reminded of Amy Poehler’s autobiography, Yes Please (which you should go buy right now).2 She was very candid in her book about her support system for her kids and herself as a single parent. She expressed how grateful and fortunate she was to have people in her life to help her. And sitting there in bed, reading this book and thinking about another, a train of thought hit me like a…train.

What about those less fortunate parents? The ones that can’t afford the support.
The ones that aren’t as lucky as my spirit animal Amy Poehler.
What about them? No one should have to do it alone.
How can I help? What can I do to help?
What can I
Could I make it a career?
Who cares about that—how can I help?
What do they need help with?

It was a lot of rapid questions, but my very Type A mind had the answer:

Their to-do lists are too long.
Make their jobs their only jobs.
Let them come home to a clean home.

And just like that, a plan was born:

to start a nonprofit organization that provided free home cleaning services
to low-income, single-parent households.

The next day, I started to research. In my county of less than 800,000 people, 8% of households are single-parent and yet they make up 22% of all households in poverty. And with increasing costs of living and static minimum wage, the number of single-parent households in poverty is rising three times faster than the total number of single-parent households.

These folks are struggling and cleaning homes is a small action. It can’t and won’t fix their lives. It can’t pull them out of poverty. But maybe it can help alleviate some of the stress and frustration. Maybe these parents can have more time with their kids. Maybe they won’t feel like they’re alone. Maybe they’ll just get a couple extra seconds to breathe.


So after six months of waiting for another potentially great job to appear one morning on a job website, I found myself with this possibly wonderful, probably going to fail idea sitting in my lap. It had all the big points I cared about: helping people, working outside the 9-5 box, making things clean and organized, and getting the chance to see inside other people’s homes (my spirit animal understands me on this one). Why wait any longer? And you know, Zorg was right when he said, “if you want something done, do it yourself.”3 Yeah, he was trying to steal magic stones and destroy Earth when he said it, so contextually, it’s not the best saying to live by, but I appreciate his determination and sentiment. If I wanted to find my happy job, maybe I needed to stop waiting for it, and just do it.


There are three truths for starting a business:

  1. It will be a shit show at the beginning no matter what you do.
  2. It is very probable that you will fail.
  3. If it’s something you’re passionate about, you’ll ignore the first two and do it anyway.

1. Kelley, Barbara and Shannon Kelley. Undecided: How to Ditch the Endless Quest for Perfect and Find the Career—and Life—That’s Right for You. (Seal Press, 2011)
2. Poehler, Amy. Yes Please. (Day Street Books, 2014)
3. The Fifth Element, 1997

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