My Advice to Teenagers on Entrepreneurship and Life

Jackie Shimshoni
Startups & Investment
4 min readDec 10, 2015

Last week, I was working at AlphaLab when I found myself talking to one of the members of this session’s cohort. We were talking about our respective paths to how we both found ourselves working in that building — myself, hired right after completing my arts management master’s program to run Startable Pittsburgh, and he having put his undergraduate degree on hold after getting the funding to start his company. He seemed really sheepish telling me about this after I had just told him about my 7-year university odyssey.

So when I loudly said “That’s AWESOME! Good for you.” he seemed pretty surprised, to say the least. “You might be the first person who’s had that response,” he told me.

It might have seemed hypocritical or even dangerous for me to say, considering I run teen programming and have two degrees from two phenomenal universities. Don’t misunderstand me; I’m glad I did it, and I’m very, very proud of what I accomplished there.

But I also acknowledge that this experience, while it was good for me, is not good for everyone. And that by no means makes someone who it is not good for less intelligent or less capable. It infuriates me that this is the message we send in a society where in fact, indebted college graduates are consistently un- or underemployed.

That being said, I have some advice for teenagers in their second half of high school on figuring out what they want to do or be:

If you’re someone like I was when I was 17, who simply knew I liked reading and writing and learning, then by all means get some scholarships and go to college. If you don’t have any idea what you’re doing, go to college or trade school, preferably one that will offer you some money to do so. If you like working with your hands and can’t imagine a life of sitting at a desk, don’t you dare let anyone tell you manufacturing/skilled trade work is beneath you — our infrastructure desperately needs individuals with specialized skill sets, and it pays pretty well. And if you want to be an artist, go to art school. Your life will be tough (mostly because of the disparaging remarks people will make about going to art school), but you will be ok. Better than ok. You will understand how to take and give constructive criticism, cry it out discreetly in the bathroom, and then come out stronger and ready to apply this information toward becoming consistently better. You will learn to come up with creative solutions, and how to work really, really hard. You will learn that any project worth doing is never truly done, just due. Any profession, artistic or otherwise, is lucky to have these people.

If you have an idea or a dream or a vision, if you want to work for yourself, if you are driven and bright, if you want to change the world: start out by going to college or trade school to learn in your preferred area. But at night, on weekends, at 5am before anyone else is up, be an entrepreneur. When you get an opportunity, seize it. Fail. Fail hard. Go cry discreetly in the bathroom, then come out ready to do it again (I’m not kidding when I say art school was the best thing I ever did).

And if you happen to live in Pittsburgh…apply to Startable Pittsburgh. Just kidding! Sort of.

I’m not the type that likes to tell someone to do something without providing additional resources. And I’m certainly not the type that thinks a teenager wants some preachy, self-sabotaging article telling them “learn entrepreneurship because your grades will increase by x%”. Instead, I will post here the same list that I recently gave to a teenager I met with, who had a feeling that he might want to be an entrepreneur, but had no idea where to start (this is common).

That list is:

The Art of the Start by Guy Kawasaki and The Lean Startup by Eric Ries. These two books are great and lay out the whole process of getting a business started — and more importantly, emphasizes why you do not need to be wealthy or have unlimited subject area knowledge to do so.

Something that we have all of our students use is the Business Model Canvas. It’s a great way to ask yourself many of the hard questions a new business needs to ask, without having to create a long, exhaustive business plan (which never hurts to have, but ultimately very few people will read).

This TED talk speaks to the idea of starting your business with a “why” rather than a “what”. Chris Millard, AlphaLab Gear’s Assistant Program Manager, cites this as one of his favorite videos and we show it to all of our students on the first day of the Startable Pittsburgh program.

My very last piece of advice: you might hate being an entrepreneur. You might realize it’s not your thing. And that’s totally ok too. Work hard, be humble, make friends and say please and thank you. Don’t let adults, my age or older, make you feel you aren’t worthy of having your voice heard. Don’t let your peers who give up too soon inspire you to do the same. You can change the world. I hope you do.

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Jackie Shimshoni
Startups & Investment

Program Coordinator @startablepgh. Devoted to making the world better through breaking down educational silos. Shameless bibliophile and lifelong learner.