How Finding Your People Can Help You Achieve Your Big Dreams

We've all had big ambitions that felt impossible. From the time we were kids, we start dreaming for realities just out of our reach – like running away from home and living in a treehouse in the woods (or was that just me?)

But as we get older, those dreams start to change. We want to score a job role that we're not qualified for. We want to bootstrap a company with hardly any money. We want to be our own boss and have the lifestyle to match it.

When our ambitions get bigger, the actions we need to take to make those dreams come true start to feel insurmountable; some of us give up before we've even started. But what if there was a foolproof way to break through the barriers between where we are now and where we want to be?

Chris Upperman grew up as part of the lower-middle class. He wasn't born into money or privilege, but through a serendipitous combination of grit, resilience, and opportunity, he's now the Manager of Governance & Strategic Initiatives for Facebook – and before that, he worked in the Obama administration as well as on the Biden Harris transition team.

Alongside his incredible work ethic and resilience, Chris opened doors that he never would have thought possible by employing a genius strategy: he found himself an ecosystem. Let's talk about it. 

We've all heard the term 'networking' before. It's been overused in the business world, bringing to mind images of self-important people working a room full of strangers. But networking doesn't have to be icky – and it's definitely not just for extroverts.

That's why lots of people refer to networking as 'ecosystem building.' It's a way of finding the people, places, and resources that can help you achieve your goals. To find your ecosystem is to build relationships with others who have something to offer, whether that be advice, mentorship, contacts, or opportunities.

I came across this article on LinkedIn the other day. Author Rina Ong-Liebnitz, one of the senior execs at Gartner, describes ecosystems so eloquently:

"I am reminded of those wonderful stories about the lone villager who went out and planted a tree every day and eventually reforested an entire mountain. We need to do the same in building our connections ... Every little bit of effort we put into connecting with others increases the odds that some will take root."

The reason I share about ecosystem building is that Chris Upperman – the inspiration of today's newsletter, and one of my podcast guests from last year – launched his career by finding and planting himself in the right ecosystem.

But it wasn't a simple start. Coming from a low socio-economic background and having limited access to opportunities, Chris had a lot of challenges and roadblocks early on. He still marvels at where he is in his career today, and how he got there. 

“I just honestly couldn't believe that I'd be at a place such as this. If you go through the arc of my resume – my accomplishments and things – and what it doesn't show is all the ups and downs. The challenges. Resilience has played a key factor in all of these things.”

Though Chris didn't grow up with money or access, he was raised to know two things: one, high effort equals high reward; and two, look for the opportunities you want. 

“I come from a very solidly middle class; some would consider it lower middle class. My dad was in the Navy, my mother became a school bus driver for the local school district that I was in, and my brother and I did a lot of service in the community that I grew up in.”

Chris knew what it meant to work, and work hard; he worked from the time he was in school and all throughout college, until landing his first job at the Bank of America. 

The 2008 economic recession hit the financial sector hard – you remember. It was utter chaos. Many people lost their jobs, and those who kept theirs were working long hours for little pay. It was during this time that Chris began to consider a different path.

“As I finished my undergrad studies, I was working at Bank of America. This was going right into the economic recession; I could see the writing on the wall.”

Going in to work every day, Chris was growing more and more impatient with the lack of proactivity he saw. He wanted to branch out and escape the crisis – but where? And what?

“At the same time, Barack Obama was running for office. It's no secret that not a lot of black people at that time believed a black man could actually become a president. And so I was very inspired by him; I knew that there was an opportunity.”

Here I really got to understand Chris's opportunist side. The 2008 recession was so devastating that most people were doing anything they could to stay secure – even if that meant being paid a little less in order to keep your job, or working longer hours. Chris took a leap of faith at the scariest possible time to do so. 

"Obama gets elected, and it's like, whoa, okay. This is a real thing. Something laid on my heart to move to DC. So I moved to DC and applied to the White House Internship Program.”

The 'White House Internship Program' wasn't exactly a glamorous position. In fact, it was quite the opposite – an entry-level job in the mail room. But for Chris, this was his ticket into a world of opportunity. He wanted to get involved in that world, and an unpaid internship was his ticket. 

Colleagues weren't so supportive; it seemed as though he was the only one (aside from his partner and parents) who believed this was a good move.

“I came into the job that I had at the time, and people were like, ‘Come on. That's for other people. It's Washington, DC – you don't have any connections.’”

Now, here's a crucial point in the story. Chris did not have any connections, it's true, but that was exactly why he saw this as such a great opportunity. He was coming in with no preconceptions, no expectations, and no baggage. He simply wanted to immerse himself in the ecosystem. 

“I did not get into the White House Internship Program immediately; I got an Associate Program, which is like a sub tier. That was a pivotal moment, both professionally and personally, because I basically threw caution to the wind. I trusted my gut.”

Chris made an incredibly smart move by taking the mailroom position, even if it probably felt like a demotion at the time. 

“I did four months in this associate program in the mailroom. There was no salary. They said, ‘hey, we got some mail that we still have to sort – are you willing to be willing to take that?’ And I said, ‘Yes, I'm willing to take that.’ And that was a really pivotal moment, because I got my foot in the door.”

But this wasn't just an aimless attempt at getting into the government. Chris had a long-term plan to give back to his community. 

“The government at times isn't responsive, and so the dream was that I would have the ability to take [responses] back to everybody. My parents raised me to be conscious of my community, and to be conscious of those who are not fortunate enough to be able to influence things that they are going to experience.”

Four months in a mailroom is a long time, but it was worth the wait for Chris. He spent valuable time reaching out to network with different people who could help him achieve his goals. 

“My wife helped me purchase a set of golf clubs from Dick's Sporting Goods. I got my navy blazer with a gold buttons, super cringe and stereotypical and cheesy. I go to these places and meet these people and start playing golf. And I started to get calls on my cell phone.”

Just like that, Chris was put in touch with one of the most influential people in his circles – someone who could propel his career forward. 

“At the time, there was this woman who was on Capitol Hill, and a lot of young black professionals that come through Washington DC eventually meet this woman. You kind of gotta go through this woman so that she can size you up and figure out where you should go.”

The woman Chris referred to is Congresswoman Eleanor Holmes Norton. She's considered almost a 'godmother' for black professionals in D.C.; she's a mentor, a professional, and an incredible resource. Chris got a meeting with her unexpectedly, and things began to move quickly from there.

“Next day, I got a call to interview in several members of Congress office. It worked just like that. It really worked just like that.”

From that point onward, Chris was able to work in multiple areas of Congress and connect with different people who helped him learn and grow. 

"I worked for Congresswoman Eleanor Holmes Norton; I worked initially in her district office before getting to her legislative office and being an aide to her, traveling around DC and going to speaking events and meetings and things of that nature.”

For Chris, this was so close to his dream. He was witnessing what it meant to have an influential voice. Soon enough, he was able to be an influential voice himself. 

“I had a small team of volunteers that were very committed to the students of America and reading letters. Some of those letters got up to President Obama. I was able to draft letters on behalf of the President to go back to the students and young citizens.”

What a powerful journey. Chris went from being a lowly mailroom worker to a presidential aide – all because he had a vision for the change he wanted to make in the world, and he sought out the people and opportunities that would get him there.

“I don't come from a family of politics. I absolutely don't come from the White House and Congress, Capitol hills, foreign dignitaries, Cabinet Secretaries. But for the last 13-14 years, there have been moments where I've actually been in front of audiences and telling them how to engage with your member of Congress so that they can hear your voice.” 

Eventually, Chris moved into other areas; he dabbled in HR and admin, advisory positions, and even branched out to work in the entrepreneurial space and being involved with the Obama Foundation’s My Brother’s Keeper Alliance.

“Then Facebook reached out. I started getting recruited to think about governance and Facebook's impact on society and society's impact on Facebook.”

This was something completely new for Chris, but he couldn't ignore the appeal of influencing change at such a large company. Fast-forward to now, and he's Facebook's Manager of Governance & Strategic Initiatives. 

“The dream was to give back, and to be engaged in this civic engagement ecosystem. And the dream on top of that was to bring that back to the communities that matter most to me.”

There's no doubt that Chris is an outstanding individual with a great work ethic and resilience to boot. But what's even more inspiring is that he didn't just stumble into these amazing opportunities – he actively sought them out.

If you've got big dreams, it's important to find your ecosystem. Whether that means moving to a new city, joining a professional organization, or attending events and networking like crazy, put yourself in the path of opportunity. You never know who you'll meet or what might come from it.

“When you get that call, be ready to act. Be in those ecosystems. If you want to get into Wall Street and you want to get into banking, you got to move to New York – you just got to do it.”

I hope you found this story as inspirational as I did. If you're interested in hearing the full story, check it out here on the podcast. Thanks for reading!

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