Ten Lessons from Mad Men’s Don Draper

Brand Boost Podcast Episode 68

1. Think outside the box

“If you don’t like what is being said, then change the conversation.”

Often times, we feel we are forced to accept things being told to us. In business, especially in advertising or marketing, we need to change the conversation in order to be heard.

Don Draper is a master at this. One scene in particular that struck me was in Season Six, episode 11. While pitching to (I believe) Ocean Spray, the client says the budget is far too high and there is no way around it. Don uses his quick wit to spin the conversation on a completely unrelated topic, which, then has the client nearly double the original budget.

Well played, Mr. Draper, well played.

2. Play on emotion

“Advertising is based on one thing — happiness.”

This should be no shocker.

Consumers often don’t care about product specs. They care about how they feel when using your product or service. Make them happy, and they won’t forget you.

3. Focus on customer retention, more than lead generation

“What’s happiness? It’s a moment before you need more happiness.”

I preach this daily. Stop always trying to acquire new customers when you can’t service the ones you already have.

A bird in hand is worth more than two in the bush.

The devil you know is better than the devil you don’t.

I don’t know, fill in any one of those here. They both work. Draper knows you need to keep customers happy because happiness is a temporary state.

4. Fail fast and move on

“I have a life and it only goes in one direction — forward.”

Resiliency is something that is key in life and in business. Really not much of an explanation needed here. When you fail, fail. Move on, get over it and work toward the next success.

5. Not everything is as it seems

“The reason you haven’t felt it is because it doesn’t exist. What you call ‘love’ was invented by guys like me — to sell Nylons.”

This one is interesting, and is my favorite, but also quite dark.

It reminds me of holidays like Valentine’s Day. Something created to sell more cards, chocolate and roses.

Really makes you think about many things we’re led to believe. As a businessperson, this is a great lesson because when selling, you must oftentimes create something out of nothing.

6. Stop talking, start doing

Roger: What is the meaning of life? Don: “I don’t know. Life being lived? I’d like to stop talking about it and get back to it.”

So powerful.

Are you doing a lot of talking and not taking enough action? We see too many flapping their gums and not creating or taking action.

Listen to Don, get out there and live life (or create content, or get to work!)

7. Bring a constant stream of ideas

“I’m sure you do (have ideas). Sterling Cooper has more failed artists and intellectuals than the Third Reich.”

Ideas make the world go ‘round. Ideas are grand.

Everyone has them.

Be sure to have a steady stream of them.

Pro Tip: Keep a notebook by your bed. Anytime you wake up in the middle of the night, or in the morning with an idea or thought, even if it seems irrelevant, write it down.

8. Roll with the constant pace of digital change

“Change is neither good nor bad. It simply is.”

Another great Draper-ism.

You can’t fight change. It happens. Accept it or be left behind.

9. Be brave — fail often

“I’m glad this is an environment where you feel free to fail.”

Don said this to Peggy. One of those scenes that stood out to me, I forget the exact season and episode. At the time, I didn’t know if he was mocking her or being serious. (I think he was mocking her, personally)

Either way, when you feel free to fail, and you are brave enough to fail, you take the chances necessary to make it in business. You also live life to its fullest. So this works either way.

10. Look at things from another angle

“Everyone else’s tobacco is poisonous. Lucky Strike’s is toasted.”

The major account held by Sterling Cooper was cigarette brand, Lucky Strike. We know tobacco products aren’t safe, and as an advertising agency, how on earth do you pitch a poisonous product to consumers?


Look at it from a different angle!

The toasting process is something every cigarette brand had to do to make tobacco, however, no one was pitching their product as such.

I love learning things from any content I consume, even the amazing television series that are on AMC. You don’t have to look hard to find inspiration or learn lessons, sometimes it’s right in front of your face.

Do you have an unorthodox vehicle of inspiration? Drop it in the comments below.