5 things “Mad Men” taught me about freelancing


Unending smoking, drinking, office sex and smarminess…oh, yes, Mad Men, your craziness of the 1960s is a world totally removed from today’s social and political correctness.

But still, the basics of getting through life remain the same. Life is competitive and sometimes harsh and Don Draper and Friends – ( in spite of their ongoing bad behavior) – have figured out their own ways to navigate turbulent business waters. And so, here are the 5 Things “Mad Men” has taught me about freelancing.

Roger Sterling, Partner at Sterling Cooper Draper Pryce advertising “You know what my father used to say? ‘Being with a client is like being in a marriage. Sometimes you get into it for the wrong reasons, and eventually they hit you in the face.'” 

Have you ever taken on a job that just doesn’t feel right? It’s like the minute you say “yes” your alarms all start to go off and something in your gut says “uh oh.” Unfortunately, many freelancers who are trying to build a business ignore their gut and press forward, discovering later that they are in for many sleepless nights. I don’t know what it is about our “sixth sense,” that can somehow sniff out wrong fits, but I’ve started to pay more attention to the signs. These can include:

  • Losing sleep over the decision to accept the job
  • Feeling resentful while working on the project
  • Procrastination when working on the project
  • A desire to quit or dissolve the contract
  • Physical reactions – headaches, stomach aches, unhappiness, fear, anger

Why do we take on wrong clients and jobs? In my own case, I’ve narrowed it down to two recurring reasons: Wanting the income, and being convinced that that the client needs me (eg., “you are the only one who can help us.”) Neither are good enough reasons, on their own, to take on a client.

In analyzing the characteristics of “wrong jobs/clients” over the years, I discovered that they were usually excruciatingly time consuming, with the client practically expecting brain surgery and nuclear fusion for very little money. They basically sucked the life out of me and I didn’t enjoy the work.

It’s taken me a few years to be brave enough to turn down a paying job when it didn’t feel right. At first, the little voice in my head told me I was being too picky, I should be happy to have the work, and every little bit of money helps, blah, blah, and blah. However, just like there are people who I choose not to be friends with, there are clients who I now choose not to work with. This does not mean they are bad people or faulty in any way. It just means that, like a marriage or a friendship, the chemistry isn’t right, the timing is wrong, our visions are different, or the time involvement doesn’t fit.

Finally, many times the compensation is simply too small for the scope of the work that the company expects. On the flip side, donating my time and work to non-profits I care about is a core philosophy – I totally believe in working for free and giving back and I think everyone should try to donate something, as there are so many community agencies that need support and assistance. However, I don’t think we need to give away our services to paying companies who just don’t want to compensate us what we are worth.

Don Draper, Creative Director at the Sterling Cooper “If you don’t like what’s being said, change the conversation.”

A few years ago, I realized that I wanted to change the “conversation” I was having about myself and who I was professionally. I realized that if I wanted to achieve my lifelong dream of being a full-time professional writer, I was the only person who could get me to that goal. I had been a public relations professional for nearly 30 years, and owned my own PR agency. I was happy and doing well, but it was time to continue in my evolution.

So, I made a very conscious decision to focus on my freelance writing for magazines and newspapers, while also seeking out corporate and government writing projects. Gradually, as I began to self-identify as an author and writer, others also began to see me in that role, and soon people and businesses were coming to me with writing projects. I was also approached to ghostwrite a book, and I currently have my own books in the works.

The lesson for me in Don Draper’s statement is that we control our own destiny and if we have a dream and a goal, we are the only ones who can make it happen. My favorite philosopher, Joseph Campbell, said it another way – “Follow your bliss and the universe will open doors where there were only walls.” He also said, “Your life is the fruit of your own doing. You have no one to blame but yourself.”

Don Draper “You want some respect? Go out there and get it for yourself.”

See above.

Joan Harris, Office Manager at Sterling Cooper “But that’s life. One minute you’re on top of the world, the next minute some secretary’s running you over with a lawnmower.”

Ah yes, been there, done that. One day, everything is running along smoothly. You’re cranking out good work, you are winning awards, people are asking you to “do coffee,” and you feel like you are totally on the right track. Then suddenly the next day a client gets mad at you, you miss a deadline, you lose a potential job bid, you get fired. You begin to wonder what the hell you were even thinking going into business for yourself.

For freelancers and small, independent business owners, being “run over by a lawnmower” can be way more difficult than it would be for someone who works in an office with a support system that includes co-workers, a boss and others who can help shoulder the burden. As freelancers WE are our own bosses, and often we work alone every day in a small home office. We don’t have a co-worker down the hall who we can commiserate with, and no team to meet with and discuss options and solutions. (However, I do have a team of two dogs who sleep at my feet and are all ears if I need to complain about something, although they don’t offer much advice).

This is why one of the most important things freelancers and small business owners can do is to create a network of peers, colleagues, friends, even competitors who we can get together with on a regular basis, discuss challenges, problems and ideas, and just get out of our solitary worlds. Join professional groups, go to regular meetings. Grab a cup of coffee or a beer occasionally with someone you enjoy. It’s amazing how quickly your spirit, self-confidence and creativity can be boosted just by talking with someone with an outside perspective.

Don Draper and Peggy Olson, copywriter at Sterling Cooper Don: “It’s your job. I give you money. You give me ideas.” Peggy: “But you never thank me.” Don: “That’s what the money is for!”

Sigh. How many of us have worked for people who believe that a paycheck is all that anyone needs to be fulfilled in a job. True, we work for a living and we certainly like those checks coming in, but personally, I believe it is also important to know I’ve made a difference as a human being, not just a name on the “Pay to the Order Of” line on a check.

When people say “thank you” they create goodwill among their employees and contractors and, in turn, they will receive more loyalty, more output, and better attitudes from the people who are doing their work. It’s not so hard. And, it could be just the thing one person needs that day.

As philosopher Alfred North Whitehead wrote, “No one who achieves success does so without the help of others. The wise and confident acknowledge this help with gratitude.”

And, finally, one of Don Draper’s more philosophical thoughts.

 “It’s your life. You don’t know how long it’s gonna last… You’ve gotta move forward… as soon as you can figure out what that means.”


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4 Responses

  1. Henrique says:

    I’m a freelance illustrator, and a huge fan of Mad Men. It’s amazing how you brought these two things together in this text. Really inspiring! I’m glad I found your blog!

  2. Patti Murphy says:

    When you outlined your physical reactions for your first point, I thought, “Oh yeah. I relate.”

    They call it a gut instinct for a reason and I recall a few contracts that put me off my food.

    And before you get accused of commenting on your own blog, I’m the Patti Murphy from Ottawa, Canada.

    • Patti Murphy says:

      Hi Patti, nice to see you here and thanks for your comments! I laughed when I saw how you identified yourself. Its so funny that we have the same name, we are both writers, you are Canadian and my mother is (was) Canadian. I’ve enjoyed keeping up with you. Thanks for checking in!