How to Build Relationships in Your 20’s, 30’s, 40’s, and 50’s (And Be Happier)


I’m 40 years old. I’m at this weird place where I now work with people both significantly older than me… and younger than me. I’m at this midway point where in my interactions and relationships, it spans from “kids” straight out of college in their first professional job, to “carmudgeons” who are on the cusp of retirement.

We know having great relationships are key to a deep network, to our success, and, most importantly, to our happiness. Over the next few journals, I’ll separate fact from stereotypes, and offer takeaways for you to create great relationships with folks at any age!

Not That Big a Deal

“Most of the evidence for generational differences in preferences and values suggests that differences between these groups are quite small.” — King

“The most important lesson is to see past the stereotypes. Generational differences are real, but we tend to make too much of them.” — Davy

Research shows that although there are trends within age groups, those differences are not as great as we treat them as. In actuality, it’s our assumptions of people in that age range that dictate how we treat them, which then reinforces that stereotype!

For example, a 20 year old has to instruct a 60 year old on a new piece of technology. The 20 year will assume the 60 year will not learn quickly, and therefore ends up giving worse instructions, which then causes the 60 year old to not learn as well. Chicken and the egg! (Example drawn from the research in Generational Differences At Work Are Small. Thinking They’re Big Affects Our Behavior)

Takeaway — Challenge your mental model of people and how you treat them.

20’s — Here’s How Millennials Deal With Stress, And How It Can Help You

Nadia Murad — A Yazidi survivor of Genocide/human trafficking, 2018 Nobel prize laureate, Advocate for victims of sexual violence. Founder of @nadiasinitiative

When I flip through magazines like Fast Company or even GQ, I see tons of 20 year olds just killing it in their field. They’re disrupting their industry and coming up with ideas that make me wonder, “why didn’t I think of that?!” But then I go to work and see 20 year olds and think, “geez, they have so much to learn.”

The reality is, it’s me that has much to learn. Here’s why.

In my research, here are two traits about people in their 20’s:

  1. “This is the most age-segregated society that’s ever been. Vast numbers of younger people are likely to live into their 90s without contact with older people. As a result, young people’s view of aging is highly unrealistic and absurd.” — Cornell University professor Karl Pillemer
  2. “People in their twenties and early thirties are in a relatively negative state of mind. This age group experiences a sharp increase in ongoing stress, characterized by the most negative thoughts and the least positive emotions, compared to other age groups.” — Zilca

How do people in their 20’s cope with stress? Again, we turn to the Happify data of over 250,000 users.

  • “Millennials” are actually quite aware of the stress in their lives (even if older folks may think otherwise.)
  • Workout regimens
  • Relaxing in bed

So how do we use this information to create stronger relationships with people in their 20’s? As with any relationship, don’t just meet them halfway, I encourage you to make an effort to meet them where they are. Try communicating more via text and apps, versus over the phone and in person. Bond over common interests that involve workouts and healthy diets. Consider sharing stories that from your experience, but make sure your purpose is to enhance their life and not to show off.

30’s — Unanswerable Questions


When I was in my 20’s, I had boundless ambition and was rushing towards everything. Career growth, check. Girlfriend, check. Working out, buy a house, get a car, check, check, check.

Then in my 30’s, my marriage fell apart as I started traveling to more remote places. My career was still rising until it wasn’t anymore. Shit happens but I found myself asking, what’s the point of it all? It was only as I turned 40 (just 3 months ago!) that I started arriving at my truth.

Gen Y (age 25+ to 39) and common trends:

  • “Sense of immediacy, look for ways to exploit the moment rather than defer to an uncertain future.” — Erickson
  • Desire for “remixed” rewards, which is fancy talk for flexible work arrangements, including ways to give back to society
  • Prioritize personal fulfillment, such as hobbies

To me, it all makes sense. People late into their 20’s, after dealing with the stress of entering the workforce and becoming independent, transition to finding oneself and question their purpose in life. Society told them to get a job, but after doing so, they look around, asking, “what’s the point of it all?” So they turn to opportunities that allow them to discover that purpose, even at the cost of stability and security.

“53% of Gen Ys… who temporarily step away from work use the time to explore passions or volunteer.” [6]

“We learn to develop psychological mastery and to regulate and attenuate our emotions, or to dismiss them instead of dwelling and allowing emotions to take over.” [9]

In creating relationships with people in their late 20’s or 30’s, try cutting the small talk down to a minimum (just enough to create rapport) and diving into some deeper, philosophy questions. Ask them what their priorities are or what part of their life/job/hobbies they find most fulfilling. Chances are they will enjoy pondering these questions and might end up with a new, close relationship.

40’s — Backup Plan for your Backup Plan

@jacindaardern — Prime Minister of New Zealand, age 39

It’s been a bit disheartening that as I research how different age groups deal with life, that I’ve been following the same pattern. Here I thought I was special and unique, but then I read that the questions I have and my feelings are the same as everyone else throughout my life.

Then again, that’s also comforting. I’m not going through this alone. That means if I’m struggling, then so have others and I can learn from that. Now that I’m in my 40’s, research shows that I’ll be preoccupied with planning for my future. That’s why I just invested in a crystal ball. Hehe.

Generation X (age 40–55):

  • Given their mistrust of institutions and desire for self-reliance, Gen X’ers are natural options thinkers — in their personal lives, most have back up plans, carefully considered if something bad were to happen. — Erickson

Here’s the takeaway — to foster a deeper relationship, learn from those in their 40’s. At this point in their life, they’ve seen a lot but still have a long runway to go. Chances are, they’re thinking about that runway and how best to prepare for it. Learn from their past mistakes, learn how they’re planning for the future, and have a dialogue back and forth. Chances are, that 40 year old is seeking new knowledge that’ll help them have more control over their destiny. Forge that future together.

Holy crap, being in your 40’s sounds like a total grind! Here’s a little something to look forward to:

  • Stress levels increase more moderately during the thirties and forties, remain steady for about 20 years, and then drop sharply as retirement comes around. [9]

50+ — Who Do You Call In an Emergency?

© UNHCR/O.Laban-Mattei

Impeachment is a major inflection point in the United States. The outcome of this trial will shed some light and further define the polarization that has had a strangle hold over civil discourse.

What does that have to do with productivity, positivity, and, in our recent discussion, creating relationships with any age group? Well, have you tried creating a deep relationship with someone with a very entrenched political view?! My point is that as the impeachment trial eventually closes, let’s also look around at who we interact with daily and see how we can close that gap with empathy.

So, who do you call in an emergency? Is the answer obvious or not?

According to a study, just 6% of people over 60 said they discussed “important matters” with nonfamily members under 36. [5]

If you think that statement is obvious, I’d like to challenge your opinion on why that is. If you’re old (haha, over 60) and feel like the young doesn’t have any good life tips to offer, then you may be missing out on some crucial information — both financial opportunities and new technologies. For example, I jut got my 80 year old dad a Fitbit to “buzz” him to keep active.

Conversely, if you’re in your 20’s or 30’s, then do you have a relationship with someone old? If you don’t, then you’re missing out on wisdom and experience that can only be gained through time. For me, it’s also been a great reminder that there is a bigger arch in history. For example, when Trump got elected and the nation felt so divided, I asked an older lady that I’m close to, have you seen this before? Her response allowed me to better judge how “big” is this moment in history.


  1. For Streaming Services, Navigating Generational Differences Is Key by Larry Downes
  2. Generational Differences At Work Are Small. Thinking They’re Big Affects Our Behavior by Eden King, Lisa Finkelstein, Courtney Thomas, and Abby Corrington
  3. The Key to Preventing Generational Tension Is Remembering That Everyone Wants to Feel Valued by Liane Davey
  4. Generational Perspectives Can Strengthen Your Strategy by Tammy Erickson
  5. The U.S. Isn’t Just Getting Older. It’s Getting More Segregated by Age. by Marc Freedman and Trent Stamp
  6. How Gen Y & Boomers Will Reshape Your Agenda by Sylvia Ann Hewlett, Laura Sherbin, and Karen Sumberg
  7. Learn to Get Better at Transitions by Avivah Wittenberg-Cox
  8. Research: Millennials Think About Work Too Much by Ran Zilca
  9. Why Your Late Twenties Is the Worst Time of Your Life by Ran Zilca
  10. 5 Questions New Working Parents Should Ask Themselves by Jackie Coleman and John Coleman

Leave a Reply

%d bloggers like this: