In the Summer of 2011, I found myself at a career crossroads.
I loved everything about Yelp – the company, the product, my coworkers, the culture… It was all gravvy.
But I was starting to hate the work.
As a sales rep, I was responsible for making 60-80 cold calls a day, for a total of 3-5 hours on the phone, completely on-script, every day.
I’d learned a lot in those 6 months – lessons that would prove to play a crucial role in my entrepreneurial career down the road – but the repetitiveness of the role had started to become a burden for me.
I found myself really dreading getting out of bed in the morning – a situation I’d always promised myself I would never settle for growing up.
I was starting to get the feeling that the job might not be right for me, but at the same time, the prospect of leaving my first job after only 6 months seemed a little ridiculous to me.
It was, after all, the start of my career. I didn’t want to be some quitter, flitting from job to job with no loyalty and no spine.
I wasn’t quite sure what to do.
Advice from a friend.
Around that time, I met my friend Ram for drinks.
Ram is like my brother from another mother. We had connected when I first moved to New York in 2011.
He was working on a concert calendar mobile app at the time, and we became fast friends over our mutual interests in jam bands, tech, and startups. I respect him deeply as a friend and a mentor.
I shared my conundrum with Ram, and what he told me then continues to influence my life today:
[blockquote]Think about where you want to go. Take the time to clearly define your goals and where you want to end up in life.
Then, think about your different options as stepping stones. Each one will take you in different directions.
Take the path that takes you most in the direction of where you want to end up.[/blockquote]
Up until that point, I’d only had vague ambitions about what I wanted to do in my life.
No real clear goals, no clear set path.
In retrospect, Ram’s advice made it clear – there’d be no way to gauge what path I should take, until I took the time to clearly define where I wanted to end up.
It also helped that Ram used stepping stones for the metaphor.
Thought of as stepping stones, any decision becomes less daunting, because instead of being some huge irreversable life decision, each individual step you take is correctable over time.
You can always adjust, and even go back.
Thinking it Through.
Following Ram’s advice, I took the time to really think through my goals and aspirations.
I realized that, one day, I’d love to run my own business. I had a few ideas that I thought could be viable, and I was confident I could make them a reality.
I knew I wanted to invest my time and energy into a vision, bring a project to life, and solve a problem for a community of customers. And I knew I wanted to earn my time, location, and financial freedom.
With that clarity, the right next steps were made clear for me.
For me, learning sales had been important. But after 6 months on the job, I found that I was experiencing “diminishing marginal learning”:
After the first few weeks, I began learning less and less every day. And, at a certain point, the pain of forcing myself to perform such repetitive tasks outweighed the benefit of the marginal learning (plus the salary I was being paid).
Quitting Yelp was still one of the hardest things I’d done in my life at that point, but with my mind made about where I wanted to end up, I was able to take the next steps confidently.
Where do you want to end up?
At some point in your life, you may find yourself at similar crossroads – facing a decision that can really impact the direction of your life.
Maybe you’re applying to different schools.
Maybe you’re making the decision whether or not to even go to school.
Maybe you’re considering which jobs to apply to, or which job to accept.
Or maybe, like me, you’d like to start a business some day, but aren’t sure whether the time is right (Hint: the time is never right. Start now.)
These decisions can be tough. And yes, it’s hard to connect the dots looking forward.
But in those times, clearly defining where you want to end up in life is the first step.
“Would you tell me, please, which way I ought to go from here?” asked Alice.
“That depends a good deal on where you want to get to,” said the Cat.
“I don’t much care where –” said Alice.
“Then it doesn’t matter which way you go,” said the Cat.
So take the time.
Dig deep, and think: if everything was perfect, and there was no chance of failure, where would you be in 3 years? In 5 years? In 10?
That’s no easy task, and certainly nothing to be glanced over. (Perhaps the subject of a future post?)
But, once you’ve nailed that down, deciding which of the paths to take becomes much clearer, and you’ll have all the more conviction as you begin to take the first steps towards your goals.