Ask a Millennial: SUCCESS Staffers Try Tackling the Generational Divide

UPDATED: June 7, 2023
PUBLISHED: July 11, 2017
Ask a Millennial: SUCCESS Staffers Try Tackling the Generational Divide

Avocado toast. Snapchat. Cracked iPhone screens. Rented duplexes. These kids today, all they do is…

Create the magazine you’re holding in your hands. Every month. You might not know it, since 120-year-old SUCCESS is so enthusiastic about the timeless lessons in personal development—devised by people who are now in their golden years or, in some cases, long dead—but the print and web editors who uphold the brand today are all millennials, that much-talked-about but poorly understood group born between the early 1980s and mid-1990s. Editor-in-Chief Josh Ellis and his SUCCESS Insider co-host Shelby Skrhak of are the elders of the bunch, both in their early to mid-30s. But the rest of the people responsible for the magazine you read each month are 20-somethings. And it’s not lost on any of us that the average SUCCESS reader ranges between his or her late 30s and early 60s.

With Millennial Whisperer Simon Sinek as our cover guy this month, not to mention an entire issue devoted to partnership, the editors sat down to discuss how their age group works, how greater connections can be forged between theirs and previous generations, and how SUCCESS content can be valuable to people of all ages. The meeting was led by SUCCESS General Manager Jim McCabe, a baby boomer. (But one of the good ones.)

Ask a Millennial

Jim McCabe: We’re here today to continue the discussion that really crystallized around Simon Sinek’s viral interview with Tom Bilyeu on Inside Quest and the topic of millennials—how they live and work, and how older generations can come to terms with that, help them and get the most out of them. I think it took off because it was the first time somebody had aggressively and authoritatively stated as fact this perception that the younger generation has been coddled or that they are not as tough, as prepared, as ambitious or as respectful as previous generations.

Related: It’s Time to Stop Dissing Millennials

Whether they know it or not, the gap between millennials, Gen-Xers, boomers and anyone else is not that wide.

Now that’s been said of every generation that comes along. My father’s generation thought it about me, and his father’s generation thought it about him. But we have this unique thing here, this dichotomy: We have a magazine and a brand that for a long time have been associated with a group of people who are of a more traditional personal-development mindset. The magazine has studied and still studies Dale Carnegie and Napoleon Hill, Zig Ziglar and the other greats. These are people who told their audiences the things they need to do to succeed. But I’ve realized in managing young people and having my own kids that the audience’s tastes have changed.

Ask a Millennial

So now we’re telling experiential stories, which is how I think people now value information about growth and sacrifice, goal-setting, achievement and self-reflection. You guys and our writers are actually doing these things every month and telling the reader how it went so they can apply it for themselves, not just giving a laundry list of steps to follow. The reader might think about personal development in traditional ways, but now, no matter their age, they’re learning the same way that millennials are learning now. And here’s our dialogue: Whether they know it or not, the gap between millennials, Gen-Xers, boomers and anyone else is not that wide.

If they’re all going to learn like millennials, they deserve to understand how millennials learn, communicate and grow. So, my first question…

What does it take for you to value someone’s advice?

Garrett Hughes: For me, they pretty much need to have been there and done it. Their own story has to very much be in line with mine, as an individual—where I’m coming from, what I’ve experienced—because otherwise some of the things they’ve faced in their day or through their background might not apply to me in the same way. I think as an individual. And I think most millennials are that way. Everybody wants to be themselves.

Lydia Sweatt: And there’s value in personally knowing someone who is giving the advice and them knowing you. I want to be able to talk to them as people rather than take advice from some public figure offering generic advice for a mass audience.

Jesus Jimenez: I also think that when it comes to getting advice from people you know, a big difference is that it’s elicited. For another story in the August issue, I spent a lot of time with five Ask a Millennialdifferent people, older people, to get personal life advice. And a lot of it, I’ve tried to implement into my life because I went out and reached for it as opposed to hearing generalizations from some talking head. That’s unsolicited advice. I didn’t ask for that. It probably got retweeted and shared a lot online and they have a big following, but it’s going to mean more if it’s someone I know and especially if I ask for it.

Ask a Millennial

McCabe: So let me ask you about a general concept—the concept of authority. What do you think?

Jessica Krampe: I personally don’t have a problem with authority, I don’t think. I get the idea that people think our generation does have a problem, but in a corporate environment or business setting, we have bosses. And how often does someone actually undermine their boss? Because that comes with consequences.

Ask a MillennialShelby Skrhak

: Everybody is going to be different. There’s not one particular type of personality that’s right or wrong, but Jess, you saying that you don’t have a problem with authority, is something I noticed from the very beginning when you started working here. You had a better attitude about executing requests from on high in our company—better than some other people your age that we’ve had. You’re like, “You know what, yeah, I’ve got to do it.”

And I’m not picking on you, Josh, but I would say your view of authority versus Jessica’s view of authority might be different. Would you agree, or no?

Josh Ellis: I agree that Jessica usually reacts to it better than I do, but I don’t know that I have a particular problem Ask a Millennialwith authority so long as I understand the logic of whatever the order from above is. I need it to make sense to me. That was a challenge, and there still is for me a challenge in managing people: I’m not really comfortable just telling someone to “do it this way,” without having to explain my reasoning. And sometimes I don’t even have a well-reasoned explanation. I just know how I want it. But I feel awkward giving orders in that way.

Sweatt: I agree. If you can go through a really detailed explanation and give me the beginning, the middle and the end, and I can see the logic, I’m all for it. It all makes sense to me.

McCabe: OK, so it would seem to me that most of you don’t necessarily value or accept authority figures simply because they are deemed an authority figure. Earlier in my career, the authority was the person who was responsible for reviewing what I did and the person who was going to pass judgment on my performance. I thought a lot of them were dumb, and I ended up taking a lot of their jobs, but the bottom line was that there was a game to be played.

Ask a MillennialKrampe: I don’t know that we look as far ahead as other generations in that respect. I don’t think many people our age know if they will be at the same company for 10, 20 or 30 years like some previous generations. My dad retired after 34 years at the same company. I don’t think anyone’s going to sit here and say that that’s our end goal.

We’re trying to share experiences. Hopefully people can learn from them.

Ellis: Things move and change so fast now because of technology. What would anyone’s job look like in 20 years? It’s impossible to say.

Jimenez: I think what you’re asking is whether we are more willing to defy our bosses because we don’t respect their authority or whatever, and I think that most people would agree that’s just a quick way to get in trouble or get fired.

Cecilia Meis: That’s actual insubordination, and it has consequences. But yeah, maybe we do tend to think of work in a more collaborative sense than past generations.Ask a Millennial

McCabe: So you see the future and your path forward in your careers differently. But you have goals, right? They might be different than what my goals were, but still, you have them.

Ask a MillennialMeis: Sure. It’s more short-term. Five-year goals, one-year goals: the balance of my savings account, countries I will have visited by that point, magazines I will have been published in, things like that.

Jimenez: I keep lists on my phone of, like books I want to read this year, or places I want to travel to this year, or concerts I want to see this year.

Krampe: But I feel like we’re a more flexible generation. When I was in college, I thought I would be married by 25 and have kids by 27. Well now I’m 27, and I haven’t done any of that, but I’m not dying over it. We adjust.

McCabe: So what is the process of achieving your goals, and how do you value the information and the resources you need to be able to supplement your goal Ask a Millennialplan?

Meis: At this table, I think we’re well-versed in where to go for those resources. The people in this room probably consume more personal development and thought leadership stuff than anywhere else in the country. So we know where to go to find solutions. But we’ve also been empowered to create our own growth.

Ask a MillennialSweatt: And that ability to create our own growth is important because, even with advice from the great authors and speakers in personal development, a lot of those things are not repeatable. There are a lot of factors in their lives that weren’t present in mine, and vice versa. So I take that advice and use it in ways that work, but ultimately I do my own thing. Personal development is personal.

Hughes: It goes back to being a millennial ‘snowflake’—having that one shoe just for you. Nobody else can fit in it just right.

McCabe: Is that where you see SUCCESS fitting in, then? Two or three years ago, we wrote more stories about people who did things. Now a lot of the stories are written by the people doing the things. What does that say about our mission?


: I do think our changed approach has to do with the way we here in this room absorb information, learn and apply it.

Ask a MillennialHughes: We might not take the word of some expert as gospel, but we relate to people who are like us, facing the same struggles we do.

Skrhak: Tracking the page views at, we’ve shown that people are more interested in the message than the messenger. So I think you’re right.

Personal development is personal.

Ellis: I think we appreciate a shared Ask a Millennialexperience—think of the “second screen” movement during TV shows or sporting events. We watch the game while reading Twitter to see what everyone else has to say about it, and share our own comments, too. I haven’t lived the same life that Lydia has, but I can learn something from Lydia if she’s willing to share it with me, and vice versa.

So I think we’re trying to share experiences. Our readers have experiences of their own, and we share those. Here in this room, we might not have as much experience in terms of our years, but we do have experiences. And hopefully people can learn from them and apply the lessons in their own lives.

Whether they know it or not, the gap between millennials, Gen-Xers, boomers and anyone else is not that wide.

Related: 6 Habits of Highly Successful Millennials

This article originally appeared in the August 2017 issue of SUCCESS magazine.

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