Everyone Entering the Workforce: Look Up!

What I would tell my 20 year old self and other musings…

I know I’m not from your generation. I was born in 1974, putting me squarely in the middle of Generation X. I may not have been the quintessential latchkey kid, but I did grow up watching my dad work seven days a week running his own business. With long hours to myself, I watched more “boob tube” (slang for TV) than I’d like to admit.

I’m a product of MTV, Mickey D’s, and phone cords that could stretch across entire rooms. I taught myself how to dance like Janet Jackson, wrote short stories by hand, and roamed the town on my bike whenever I felt bored.

High school gave me my first taste of leadership as captain of the dance team, where I learned about resilience—being sidelined by injury, sitting out, and eventually coming back stronger. And while we grew up in different times, I had the same inner drive I see in many of you. I wanted to be the best—not to meet someone else’s expectations, but because I expected it of myself.

So, when I entered the workforce, shiny and new, I wanted it all. I was infatuated with agency life and the glamorized idea of brainstorming campaigns for big brands around a conference table. I quickly learned that agency life wasn’t all it was cracked up to be, but that “shiny object” kept drawing me forward.

My mom opened the first door for me, cutting out a newspaper ad (yes, the print edition) for a job that read, “Write the web.” “It’s the internet—the next big thing,” she said. That first startup showed me early on that leadership—or the lack of it—can make or break a company.

At a time when AOL, Amazon, and Yahoo were new and exciting, I had a front-row seat to what happens when values are missing at the top. And because it was such a small startup (just five or six of us), I could see the leaders clearly. It wasn’t just a lack of vision that troubled me; it was their loose moral compass. I ran from that place as fast as I could.

Luckily, that experience didn’t turn me away from internet startups. Instead, I spent the next two decades chasing the shiny “internet” object through the bubble, the burst, and the new normal that followed. I jumped across industries—real estate, ad tech, dating, automotive, retail, charitable giving, and now travel—and every experience taught me something new about leadership.

It was a long time before I worked closely with an executive team again. My next role was at a large company, and I was many levels down the ladder. But I chose my managers wisely, always looking for people I respected, who were both talented and grounded. Those early mentors taught me a lot, and I observed them navigating every kind of workplace challenge. I watched them pitch ideas and sometimes saw them come to life. I saw them push for change and get frustrated when it didn’t happen. I watched them stay motivated, even as strategy shifted with the latest breeze. I learned from them, and as I moved from role to role, I kept looking forward.

When things didn’t work out, I didn’t dwell too long on why. I’d move on to the next shiny object, eager for the next adventure.

At each new company, I rose through the ranks, eventually experiencing a lot of what I’d seen my early managers go through. I felt the same highs and lows. Sometimes I was pushing a boulder up a hill, only to have it roll right back down and flatten me. Other times, it felt like shooting layups, where everything clicked, and I could high-five my team for making it happen. Eventually, I reached the C-suite, and it felt like I could do no wrong. I thought, finally, I had control over my destiny.

But here’s what I realized over my 30+ year career: No matter where you sit, forces beyond your control are always at play. The vision and values of a company start with everyone at the top—whether it’s the founding team, the C-suite, or even the investors. One person alone can’t set the full tone, and it’s the alignment (or misalignment) among them that ultimately shapes the culture and direction of the entire company. As the saying goes, “Sh*t rolls downhill,” and nowhere is this truer than in the workplace. Together, these leaders either elevate the people and teams below them or create challenges that cascade through every level.

My book, GrowUp, focuses on these top leaders for this exact reason. Moving from startup to “GrowUp” requires a balanced leadership team with a mix of superpowers—people who respect, trust, and empower each other, all rowing toward the same goal. Employees are your brand’s biggest touchpoint, and the culture you set will impact the company’s success.

For every thousand companies where sh*t rolls downhill, there’s one with a leadership team so balanced and in sync that they’re practically sprinkling pixie dust with every decision. These are the companies where people don’t drink the Kool-Aid out of fear but out of true inspiration. These are the places that will lift you up, recognize your talent, and help you go places.

Your current manager might be the nicest person in the world, but their success depends on the team above them—and how those leaders work together. My biggest piece of advice for those entering the workplace is this: Look up. Research the leaders at the top, and get a sense of who they are as people. What superpowers do they bring? How do they interact with one another? And what are their potential blind spots?

I understand it can be hard to find a job in today’s market, and sometimes it feels like the priority is just landing one. But as you step into a role, keep your eyes open. The culture and environment created by leadership can determine how far you’ll grow, the kind of support you’ll have, and whether you can do your best work. Making a habit of learning about those at the top can help you avoid situations that limit your growth and seek out companies where you can thrive. This investment in understanding leadership is just as important as the role itself for your career, no matter where you start.

You might be wondering, “That all sounds nice, but how am I supposed to do that from way down here?“ Here are a few ways to get started:

1. Look at LinkedIn profiles for each senior leader
   When you’re applying, everyone’s looking at your LinkedIn profile—make sure you’re looking at theirs too. Check out the CEO and their leadership team. Where have they worked? What roles have they held? Do they stay in places long-term or bounce around?

2. Check Glassdoor ratings for both current and past companies
   Glassdoor can be hit or miss, but you can still find clues there. Don’t just look at the overall rating. Read through the reviews, and see if there are recurring mentions of specific leaders. Patterns can tell you a lot.

3. Watch videos or other media coverage where each senior leader is quoted
   Video interviews are one of the best ways to get a sense of leaders’ personalities and styles. It’s the one medium where you can see how they come across, whether they’re humble, driven, or maybe a bit egotistical. Try to pick up on their natural personality—are they warm and caring, or more brainy and calculated? There’s no right or wrong, but understanding their approach can help you gauge whether it aligns with the type of environment where you can thrive. Media coverage, especially articles where leaders share their own experiences and values, can offer similar insights. If possible, watch or read about several team members to get a feel for the leadership team as a whole. Try to identify the unique strengths each one brings to the table. The GrowUp Superpowers can be a useful lens here; do they each bring something unique, and is there a sense of chemistry among them? This balance in leadership will impact the culture they create and the level of support you’ll experience.

4. Tap your network (or your parent’s network) to backchannel these leaders
   You may not get to interview them directly, but you can often find someone who’s worked there. Former employees can be an incredible resource. Ask them what it was like to work there, why they left, and what they saw from senior leaders.

The bottom line is this: Look up. When you’re lower in the organization, you may not always see it unless you seek it out. But understanding the leadership that guides you is essential to building a fulfilling career. Don’t get blinded by the shiny object. A company with a product you love isn’t always a company you’ll love working for.

Throughout my career, I rarely chased “unicorns”—those companies valued in the billions that defy industry norms—but I did learn to seek out companies with exceptional leaders. From experience, I’ve come to believe the real unicorns are those that put people first. They’re the ones with balanced leadership teams who respect, empower, and genuinely care for one another. They’re the companies that understand some decisions are too costly—even if they look great on paper—because they would erode the values they’ve worked so hard to build.

So as you enter the workforce, don’t just chase the next big thing. Take the time to look up. Find a place where the leaders see you, where they bring out each other’s strengths, and where they work together to create something truly great. It will make all the difference in your career journey.

To learn more about my GrowUp framework and how it can help grow your leadership style visit: Michelledenogean.com