Am I crazy spending my nights giving rides to strangers just for a shot at a dream? A letter writer is torn between taking a job and juggling Uber with grad school.

Let’s start with the pros and cons list, says our elder.

Dear EWC

Hello! I’m 24 and caught in the whirlwind of trying to establish a career but not knowing what I want that career to be and wanting to enjoy my life and have fun and adventures while I can. I have been offered a position as a receptionist at a prominent law firm in my city, 9am-6pm for $15/hr. I currently work a similar position, 8am-5pm, $14/hr. The money is not enough to live on, so I also drive Uber on the weekends. But I am seriously contemplating not taking the position because a) I don’t like office jobs. I find them dull and wearisome and not fulfilling. b) I could make the same amount of money but working half the hours by just driving Uber, and, c) I want to go to graduate school internationally or move internationally, which will require a lot of work and research that won’t be able to receive the necessary attention if I take the position. However, the job does come with benefits and opportunities. I could learn a lot, have stability, have reputability, and earn experience in an office. Am I crazy for turning down the position to spend my days in coffee shops writing essays and spending my nights giving rides to strangers just so I can have a shot at a dream?

Dave-Scott replies

In today’s world, I am sure a lot of people would just say, “Go for it — go after your dream.” And I admit that there is a lot to be said for going all in and committing yourself to make sure you get what you want out of life.
Thing is, I think that it is less about following your dream than it is working to get your dream. Nothing is going to be just handed to you because you have a dream — you have to earn it.
That said, often you have to do things that are not all that appealing as you work towards an eventually rewarding career and life. You need to start by building a foundation of work experience and education and work hard on doing a great job in both areas. You also need to pay the bills while laying this groundwork.
You are the only one who can decide what will work best for you. You don’t mention what would be your ideal career so all I can assume is that your next goal is to go to graduate school and gain expertise in a field you are interested in. I have always used lists to help me make hard decisions. A pro and con list that compares your current job, the new job, and driving for Uber might help you make a decision. Maybe more useful would be to first make a pro and con list that compares the advantages of working now, saving money, and gaining experience versus working at Uber (with its flexible schedule and money) and focusing on moving forward to obtain that advanced degree.
You are right in having a dream and wanting to pursue it, but a solid, well-organized plan is what you need to get you to that goal.
Would recommend reading You Are a Badass: How to Stop Doubting Your Greatness and Start Living an Awesome Life, by Jen Sincero. It contains a lot of good ideas.
If you have more questions, please contact me. Wishing you the best of luck — dream big.

Letter #: 415690
Category: Career