🎉 Special Edition: Lessons I've learned from a college dropout

This email is going to be a bit different. You've been warned.

In my delusional covid state earlier this week, I tried to give a friend some advice. She has a lot going on, and I reminded her to take time to herself. I told her, remember, it’s only April and you wouldn’t want to burnout this early in the year…

Except it’s October… oh wait, almost November.

I was also up late last night thinking about how this week has also flown by, and that I still hadn’t written my weekly email to all of you.

And then I heard my husband say,

“Happy anniversary!”

I looked up and realized that it was midnight. And my husband and I have officially been together for 8 years now.

Three years ago, I wrote a post in his honor and to celebrate our time together. It’s just as relevant today, as it was three years ago, and as it likely will be 10 years from now.

So for this week, I’d like to share those words with all of you. I believe you’ll find them valuable, and hopefully forgive me for not sending my usual resources.

As always, email me (or comment directly on this post - I respond to each one!) to share your thoughts. Even if you disagree - I’d love to hear from you.


4 lessons I learned from a college dropout

During the last set of elections (2016), I lost count of how many times “uneducated” and “does not have a college degree” were used interchangeably. I find it shocking that, in this day and age, people still consider those who didn’t go to college as uneducated.

Even though I grew up in the Silicon Valley, no one talked about how some of the greatest movers and shakers didn’t go to college. Instead, “college dropout” was constantly given a negative connotation.

I graduated from an elite university. My partner dropped out from one. And I can confidently say that my greatest life lessons come from him and his experiences as a college dropout.

Here are just four of those lessons.

Lesson 1: How to (actually) think critically

I took an Operations Management class during my time at USC. If you know my husband, you know he’s all about ops and efficiency. As soon as I brought my final home, he wanted to have a look. But not just a look… he wanted to take it (for fun…).

I had aced it (93%), but only after taking a semester-long class that required me to memorize lots of formulas. I let him take a stab at it - left him alone for 60 minutes (how long the final had taken me to complete). When I checked back in, he was still working his way through it. So I gave him a bit more time, suggesting that he could not possibly ace it without knowing all of the formulas.

30 minutes later, he was done. And he aced it. 100%. I couldn’t believe it. I had him walk me through some of the problems, all of which he approached logically by applying the concepts he had learned through real world experience.

He didn’t have the easy way out - my husband didn’t spend months in a classroom learning formulas that sped up the rate at which he could solve problems. He actually faced these challenges in his daily life through his work, where he was forced to critically think through each scenario and understand all aspects of a problem. So while it did take him a bit longer to find the solutions on this particular test, he demonstrated his ability to think critically, a skill that will last him a lifetime.

I reflected back on my own critical thinking skills. I had spent four months going through countless problem sets, memorizing formula after formula like I was instructed to do… but never did I stop to think if I truly understood the approach. Nor did anyone ask (or test) me on the logic behind the formulas.

I have spoken to many people on what they believe the purpose of college is.

Job security? Nope. Too many underemployed or jobless graduates.

Connections? No… not enough students possess networking skills.

Career exploration? Not sure if declaring a major and getting little to no exposure to it in the working world counts as exploration.

Critical thinking skills? That seems to be the answer people agree on. Yet I remember being asked to memorize formulas (none that I remember today), rarely being given the time to critically think through any of the concepts.

Luckily, I met my husband while I was still in school, and give thanks to him for my ability to think critically. He educated me on a crucial life-long skill.

Lesson: 2: Mentors matter

A big part of my work includes advocating for mentorships. In 11th grade, my Humanities teacher identified a characteristic in me that pushed me to consider Business as a college major (one I would have likely never considered otherwise). In college, a professor pushed me to launch an idea I had considered silly. That idea became my first company, Skillify.

But here’s the kicker: I hadn’t sought advice from any of those adults. I was just fortunate enough to be in an environment where that guidance was present.

It wasn’t until I met my husband that I realized the power of mentors.

My husband sought out mentors from an early age because he had to. He didn’t have a fancy college with robust programs. When he launched his first business idea, he couldn’t rely on an entrepreneurship program at a university to guide him. He wasn’t surrounded with professors or experienced alumni. He was in the real world, starting from scratch. So he had to identify and connect with people who could help him. He had to to take initiative. He had to ask for help. He had to put himself out there and advocate for himself.

Those mentors supported him, gave him the tough-love when he needed it, and exposed him to resources he lacked. And as a result, he developed an incredible skill: self-agency.

Meanwhile, I assumed there would always be someone to help me, that I could wait for adults to ask me about my ideas and guide me. And unfortunately, I see a lot of schools contributing to this misconception. There is so much investment in bringing better guest speakers to students, but what about teaching students how to take initiative and seek help?

Once I entered the working world, I saw firsthand how much people genuinely want to help each other, and especially those younger than them. But I also know what a difference it makes in both a mentee’s development and a mentor’s motivation when mentees actively seek out advice and have a sense of agency, versus waiting for mentors to direct them.

Lesson 3: How to find answers AND know what answers to look for

My husband googles EVERYTHING. And he reads A LOT. He also talks to anyone and everyone. When we meet people, or just make eye contact with strangers, he engages in conversation immediately. He asks tons of questions.

Why? Because my husband understands that he has to learn wherever and whenever he can. He didn’t have a class with a rigid curriculum that told him what to study and how to study it. If he needed to learn something, he had to figure out how to learn it.

Most times, he didn’t even know what he should be learning - he had to figure that out by reading everything and talking to everyone. I, on the other hand, was spoiled. I became accustomed to being told what answers to look for, and how to find them. What questions to ask and who to ask.

Going back to my earlier point - a big advantage of being able to think critically is being able to identify how to think and learn. In college, I was given a set of classes I had to take to “learn business.” But when I actually started building businesses, I realized early on (thanks again, partner!) that I couldn’t wait for someone to give me all of the answers. I had to identify what answers I needed, and then go find them.

(Side note from present-day Shireen: reading this again today makes me even more excited and convinced that Personal Learning is the answer.)

Lesson 4: Always be prepared

I’m sure you’ve heard of the common saying, “Luck is when opportunity meets preparation.”

I first heard it from my husband. I can always tell from his facial expressions when he’s running scenarios in his head. He’s actively thinking through all of the possible outcomes of a given situation. He’s preparing for all of them - the good, the bad, and the ugly.

When I first met him, I would get frustrated. I mistook his preparation for worry. Why did he need to worry so much about situations? Why couldn’t he just wait to see what happened?

If I wanted to achieve something, I followed a sequence of steps. One linear path. But this made it difficult for me to think through all of the possible paths that could exist to get to a goal. And when it came to situations, I had a hard time thinking through the possible outcomes.

But my husband - he had no paved path. He didn’t have a college counselor that mapped out his four-year plan. He wasn’t conditioned to taking one step after another, walking straight to reach his goal. He built his career by carefully analyzing all possible options and paths.

And as a result, he developed a transferable skillset. He can think through any situations, and always has a plan A, B, C, D, E…. wouldn’t you want him by your side through the good, the bad, and especially the ugly?

Don’t get me wrong…

I don’t regret pursuing college as my post-secondary option. But I am SO happy that my husband didn’t. Because frankly, the skills he taught me within our first few years together - those are truly life-long, must-have skills.

So here’s to my favorite college dropout and my greatest mentor - thank you. Thank you for taking a chance on yourself, and on me. Happy anniversary.

"If you think of it, the whole system of public education around the world is a protracted process of university entrance.

And the consequence is that many highly talented, brilliant, creative people think they’re not, because the thing they were good at at school wasn’t valued, or was actually stigmatized.”

- Sir Ken Robinson


Kudos to you for making it to the end. If you enjoyed today’s words, or just have some thoughts to share, please hit reply. I’d love to hear from you.