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What Mad Men Can Teach You About Success & Pursuing Your Passion

by Tony · 6 comments

Don Draper Mad Men

Aren’t we all still trying to please our bosses, counting down the days to the weekend, and kissing ass at every client meeting?

What has really changed from the days of Mad Men besides the clothes and cars?

I started watching Mad Men when I was still wearing a suit and hoping for a good performance review from my boss. But I have continued watching while we travel the world and I have realized something.

Mad Men is more than just entertainment. It can teach us 3 specific things about the elusive nature of success and pursuing our passions.

Spoilers lay ahead so if you have not watched Mad Men and are afraid of learning any plot points… be warned.

Also, why aren’t you watching Mad Men? It is amazing!

What We Can Learn From Mad Men

Unfulfilled Success

unsatisfied by your career?Have you ever signed that new client, fixed that critical problem, or met a brutal deadline and been lauded for your great work only to still feel empty and unfulfilled?

Don Draper’s Wife, Megan, sure has. She not only designed an entire ad campaign for Heinz but also landed the account with some quick thinking.

Peggy, someone who lives and breaths advertising, tells her, “This is as good as this job gets. Savor it.”

Not feeling the joy of her success though, Megan later confesses to Peggy that she is trying to go back into acting (her true passion) and Peggy cannot comprehend why Megan would want to leave.

But Megan voices her despair, saying “the other day they asked me to take Stan’s originals down to the printer and I thought, ‘all I have to do is throw these in the trash and they’ll fire me. Or at least they’ll yell at me and I can cry enough and quit.’”

Faced with what should be the highest of highs in her job, Megan can only think of ways to escape.

Sound familiar?

The Takeaway You should always work hard and strive for success, but it is important to understand how you feel about the success you achieve. If it leaves you fulfilled and wanting more, that is a good thing. But if it is an unfulfilling success, leaving you wanting something else, then you should do as Megan does.

Figure out what makes you fulfilled – not just in success, but even in failure. For Megan, it was her career in acting. For me, it is travel and entrepreneurship.

What is it for you?

Do Not Rely On The Dreams Of Others

Do not rely on the dreams of othersMany people, when I told them about my plans to quit and travel the world, did not understand my dream.

I was doing well, in a job that paid well, and I was well-ahead in my career compared to many of my peers.

But you cannot rely on what others think, as you never know how they attained their perspective.

After Megan quits her job to pursue her dream of acting, Don cannot understand, telling Roger Sterling, “I was raised in the 30’s. My dream was indoor plumbing!”

For Don, climbing the corporate ladder and being a success at advertising was so far beyond his wildest dreams that he could not comprehend someone who wanted anything different.

The Takeaway Everyone has their own experiences and biases that affect their personal beliefs. Do not give up on what makes you happy just because others cannot understand.

Today, with the opportunities presented by the internet and cheap flights, we can dream bigger than the generations before us. They might be happy they have achieved their indoor plumbing, but that doesn’t mean you need to be content.

Define What Success Is To You

congratulationsSo you landed that big account and made a nice bonus. Congrats!

But if you were starting from scratch and could do anything you wanted, is that how you would judge success?

A success for your company does not always translate into a personal success.

As Pete Campbell has succeeded professionally over the 5 seasons of Mad Men, with more accounts and responsibility, he seems to have become increasingly dissatisfied.

In season 5, he progressively deteriorates in each episode, as he continues to want more and cannot appreciate his successes. First cheating on his wife, then attempting to box a coworker for embarrassing him at work.

Pete has always strived to achieve the adoration of others, but he is always chasing other people’s versions of success which inevitably leads him into a spiraling descent of unhappiness.

The Takeaway If we chase what someone else considers a success, we will always be unhappy. Real success can only be defined by each you. Pete wanted a loving wife, child, and great career – not because he yearned for this, but because this is what others thought of as a good life, as a success.

Define success for yourself first, then work your butt off to achieve it. Only then will you find happiness.

Your Turn: Have you ever taken the time to define what success is? Or do you just work to accomplish what other people call a success? How do you personally judge your own success?

About Tony
Quit his job to try actually following his dreams for once... and is currently loving it. He is working hard to to make this life-style permanent by writing about his adventures and brainstorming money making opportunities with his partner-in-crime, Meg.

JR May 22, 2012 at 8:07 am

Tony, tremendous insight. This is a very hard thing for most people to really get their head around due to the perception they feel they are receiving from their peers and the need for that perception. Keep on following your passion.

Tony May 22, 2012 at 11:26 am

Thanks for the encouragement, JR! We’re doing our best!

Megan May 24, 2012 at 6:19 am

so im still trying to figure out what success is for me. proudly doing this at almost age 29. i thought it was the idealistic madmen way of life… got my undergrad in marketing my MBA in international business and realized that international business jobs were only appealing at an upper level and nothing in between was satisfying…and life is too short to spend any years unhappy. so now i am here still wondering what my definition of success is…but ive concluded that happiness = success for me. and there are more things…i just havent figured those out yet :)

Tony May 25, 2012 at 10:10 am

Thanks, Megan! Glad to hear from you again!

Happiness = Success not too shabby… if you start there I don’t know how many more things you need to figure out :)

For me, I think I have finally come to understand that I would gladly give up a high flying corporate career in order to work for myself. Now comes the tough part though… crushing it until I can finally make enough money to escape the old life!


Cherina | Quiet Wanderings May 30, 2012 at 4:33 am

Ok, so you are like the billionth person that has told me that Mad Men is awesome. Really must start watching it one of these days :)

| “Do not give up on what makes you happy just because others cannot understand.”

You have articulated this perfectly! It still amazes me how people don’t understand that need to break away from the ‘norm’. Success does not necessarily equate to happiness and to find what truly makes you happy often means taking risks (leaving your life to travel the world?)
I think any kind of happiness is a great sign of success. And happiness is not something to be taken lightly.
Kudos to you and Meg for doing what you love!

Tony May 30, 2012 at 2:14 pm

Meg doesn’t watch Mad Men either… so you are in great company!

Thanks for the great feedback, Cherina! I really appreciate it. I think people sometimes don’t realize it until they are deep into their career. I didn’t want that to be me so i’m trying to make my escape now from the corporate gig!

Plus, people never think how much risk there is in a corporate job where you could be fired at any time due to circumstances out of your control…

Thanks again for the great comment!


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