The Upside

Keep Your Eye on Your Why

It may surprise you to learn that the most pivotal job I ever had (and I’ve had dozens!) was a college babysitting job.

For one year, I was a babysitter and driver for one of two children of a wealthy family living in the leafy suburbs of Washington, DC. I say one of two because each child had their own babysitter. 

Yup, this family was private plane, personal chef, multiple luxury homes-level rich. Richer than anyone I had ever met in my 19 years.

At that time, I was earning a business degree at GW with big dreams of climbing a corporate ladder at a fancy company with a fancy office and fancy business cards and a fancy job title that would be sure to impress. 

Then, the goal was to parlay all of that into my own company where editors from Inc., Forbes and Fast Company would be lining up to have me grace their covers.

This goal felt very, very fancy to me.

The family I babysat for was all of this and more. Fancy beyond my wildest imagination. 


They were miserable. 

So miserable that I could hardly get my 9-year-old girl to crack one smile in the 12 months I was with her. She had been raised by a revolving door of sitters and unhappy parents. She wanted nothing to do with me.

This experience changed everything. 

I thought being fancy was a true sign of success and happiness. But, I was completely wrong.

It changed the course of my life because I started to realize that my goals were way off, and I was pursuing them for all the wrong reasons. 

I wanted to be fancy because I had something to prove.

I had something to prove because I was insecure.

I was insecure because I was seeking outside approval. 

Even when I received outside approval it was never enough. 

It was never enough because I needed to find it from within.

And so the loop continued.

Now, as I run my own business and help others scale theirs inside The Upside, I reference back to that babysitting job as a reminder to keep your eye on your why. 

Other than a paycheck…

Why do you work?

Why are you pursuing the path you’re currently on?

Why do (or don’t) you want to have your own business?

Why is being successful important to you?

10 years after I walked away from that babysitting job, I ran into the dad in an office building lobby on Park Avenue and 55th Street in NYC. I started asking about the kids (now adults), the wife (now divorced), and reminiscing on old times at the DC house.

And you know what? Ten minutes into the conversation… 

I realized he had no idea who I was.

Erin Halper

About the Author

Erin Halper is the founder and CEO of The Upside and the leading authority on independent consulting. Since launching The Upside in 2017, Erin has helped thousands of professionals transition from corporate life into consulting to achieve flexibility, autonomy, and a renewed sense of purpose in their careers.

Erin has been a frequent speaker at Columbia, NYU, Harvard, and Brown and has been featured as a leading future of work expert on dozens of podcasts as well as in Forbes, Business Insider, Nasdaq, Crunchbase and many more.

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