Mad Men is one of my television obsessions. A couple weeks ago, Don, an ad man and the main character, was talking to Dr. Faye Miller, who they brought in to help shape the strategy of their ad campaigns to best connect with consumers.

During the conversation, Miller said something that has stuck in my head ever since…

“It’s all about what you want vs. what’s expected of you.”

I thought this was a very interesting insight and so very true. It got me thinking about expectations and true desires and how  many times the two just don’t match  up.

When I thought about it, I realized the decisions I’ve made that “went against the grain” ended up being the ones I’m happiest with and most proud of because they truly came from my heart, and therefore ended up being what was really right for me.

Sometimes though the pressure of expectations can become overwhelming. Especially for twenty-something’s living in a big, competitive city like Chicago! I and many of my friends struggle with it every day.

I decided to really look at a couple of these expectations and compare them to the reality I see around me. Of course, this is just my perception, so feel free to disagree with me.

Career Expectations

You’ll find a career (not a job) that you are passionate about and excel at. You’ll get promotions early, raises that surpass your peers and by the time you’re 30, you’ll have the experience and power to dictate your own terms (ie working from home, vacation days, and responsibilities).

Career Reality

Many people I know moved to Chicago and took any job they could find in order to live in the big city. Five years later, most are still at those jobs, which they don’t consider a “career.” They feel terrible anxiety because they’re not passionate about what they do, and they’re overwhelmed by the thought of starting over.

Those that do have a career they’re happy with are finding that there’s no easy button to getting promoted, making more money or acquiring the power they thought they’d have by 30. They’re feeling stressed out and overwhelmed trying to “make it,” yet can’t come to terms with being anything less that the best.

Relationship Expectations

Dating in a big city comes with a ton of pre-conceived notions. If you asked most single people who move to a city out of college, they’d likely say their goals are to remain single and live it up until around 26 (varying if it’s a guy or girl), meet someone, date for three+ years, get engaged, get married, be married for 1-2 years, then finally have children. These people also say they want to have a “big family” with four or more kids. (How getting married at 32-33 leaves time to have 4+ kids is beyond me).

Relationships Reality

The reality of the dating scene for a twenty something in a city ranges widely, but from what I’ve seen, some break off great relationships or don’t give them a chance when they’re young because they aren’t “ready” while others feel pressured to find the right person as soon as they hit their “ideal” age.

Those in happy relationships are expected to not get married “too young” but also not wait until they’re “too old.” And once married,  they grapple with balancing having a family and a home while maintaining that high-powered career they fought so hard for in their twenties.

The message I am getting is that trying to live up to what we think is right just sets us up to feel like failures or pushes us into a lifestyle we don’t actually want.

Of course, expectations can serve a positive purpose too. I mean there’s a reason expectations exist in the first place…they usually outline an ideal path and can help steer someone in the right direction.

While it’s not likely that I can completely disregard expectations, I’m going to make an effort to approach decisions about my life by leading with what feels right inside first. What I (and Luke) truly think is best for US – not everyone else. I’d challenge you to do it too!

Who says your college boyfriend isn’t the man you’re supposed to marry? Why do we feel like we have to know what our life’s calling is at 22? Is it worth it to end up with the wrong person just to meet a personal age deadline?

Personally, I don’t think so, but I want to hear from you!

Do you guys feel pressured by expectations? When’s a time  you went against what everyone else thought you should do to do what felt right to you?