Five Tough Lessons Every Young Entrepreneur Must Learn

by / ⠀Startup Advice / April 30, 2013

5 Tough Lessons Every Entrepreneur Must FaceFive years ago I was 22, ambitious and inexperienced, and ready to start life as an adult. I had just landed a great job at 20th Century Fox Films and a crystal-clear vision for the future. I was on track to become a film studio executive.

Now at 28, as CEO of my own digital marketing firm in San Diego with two failed business ventures behind me, it’s sometimes funny to think how confident I was back then. I couldn’t foresee the life lessons I was preparing to learn over the next five years, nor did I care. I was a sitting duck.

Your mid-twenties will present five big challenges that you must learn from in order to succeed. The good news is that you’ll survive. Learn these five lessons early on, and you might just avoid learning the hard way. 

At 23, STOP complaining and START learning.

Fact: A moment will come when you realize that you’re not as awesome as you think you are. Accepting early on that your hard work and opinions will not always be valued is a sign of maturity that will benefit you in the future.

Here’s what not to do: Complain. Not only does it annoy coworkers, it also squanders valuable time you could spend learning from others. Every experience contains a lesson that will help you down the road, and every person has something to teach. At 23, you should work hard, swallow your pride, and absorb as much of the environment, the strategy, the tactics, the people, the politics, and the business as you can. Once you STOP complaining and start learning, you’ll start getting moving forward.

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At 24, seek “Undercover Mentors” to get ahead.

As you grow into your role, it’s important to align yourself with the key people whose talent and knowledge can drive your career forward. Finding a mentor who possesses the experience you lack can help to bridge the gap between reality and ambition.

Unlikely mentors often give the best advice if you know how to ask for it. At previous jobs, I always admired the Creative Directors. They had brilliant ideas and impressive portfolios, but they weren’t exactly interested in helping me fast track my career. But after a few awkward interactions, I got it. Instead of seeking a formal mentor, I would create opportunities for casual conversations and was always prepared for an impromptu chat about their opinions, interests, how they come up with ideas, and how they got to where they are today. These “undercover mentors” played a big role in my early career, and I doubt they even knew it.

At 25, realize that life doesn’t end at 30.

A Quarter Life Crisis is “A period of life…in which a person begins to feel doubtful about their own lives, brought on by the stress of becoming an adult.” – Wikipedia

If you haven’t experienced it already, your quarter life crisis is probably about to hit you like a ton of bricks. For me, this moment occurred when I realized that – after leaving behind my life, my job, friends, and moving to LA for work – I didn’t actually want to live in LA. I didn’t like being a small fish in a big pond, but I couldn’t just go home just yet. There was still so much to learn.

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This experience ushered in an epoch of isolation and despair that marks one of the most challenging times in my life. For the next two years I learned to value patience, perseverance, character, and long-term decision making in a way I couldn’t understand before.

My advice: take your time and figure out what it is that you do want and don’t want. Then you’ll be able to start reconnecting the dots to get where you want to go.

At 26, drop the ego and focus on networking.

Ultimately, I got canned from a job. Technically I was ‘laid off,’ but it didn’t matter. It sucked. It also taught an invaluable life lesson. At 26, I learned to drop my ego and focus on long-term networking.

Learning how to listen and take direction – sometimes at the cost of your ego – is absolutely essential to long-term career success. When I got laid off, rather than letting my pride stand in the way, I really listened to all of the well wishes and advice people offered on my way out. I knew that these people could be my potential clients, investors, and business partners someday. So I put my head down and did what I could to preserve relationships with coworkers across all levels of the company. Years later, these are the people who’ve helped me start my company and get to where I am today.

At 27, accept failure as a requirement of success.

As an entrepreneur, I realized early on that I would have to fail in order to succeed. What I didn’t realize until later was just how many times. After my first business venture, I learned that there’s such a thing as Complete Failure when I tried unsuccessfully launching an online e-commerce website for surfers. Later on, I failed to get my business up and running effectively and learned about Success-Within-Failure. These failures soon turned into the success of my current company, CreativeMob.

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Failure is good for you so long as you’re learning and evolving each time. The key is to stick with it, and keep trying new things until you get it right. The truly successful never stop learning.

I wonder if my 33-year old self will agree?

Andrew Ly is the Founder and CEO of a Digital Marketing and Technology Firm called CreativeMob. He is the driving force behind the company’s innovative culture and game-changing work. Prior to CreativeMob, Andrew has worked at various social technology start-ups, and Fortune 500 Companies, such as Universal Pictures and 20th Century Fox Filmed Entertainment. 

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About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.


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