It’s pretty hard to be a 20-something. On the verge of 22, I’ve found that navigating career, friends, and life when you’re just figuring out who you are is not something you’re taught in school.

In tandem with ambition and big dreams, it’s sometimes impossible to determine how best to build our careers, brand ourselves, and befriend a network that suits us when we’re ever-changing and ever-growing.

I sat down with the remarkable Caroline Pugh to talk about these 3 B’s – Building, Befriending, and Branding. Caroline is a knockout – the Chief of Staff to the President of CareJourney, she has a fierce independence and an old soul. I’m blown away by her every time we chat.. Others agree – she was named one of the 15 Female Entrepreneurs to Watch by Entrepreneur Magazine, and has been featured in the likes of Forbes, TechCrunch, and the Wall Street Journal.

We figured: if two twenty-somethings put their heads together and combined their unique experiences and insights, perhaps we could crack the code for these volatile and essential years.


Caroline spoke to the importance of trying to figure out what exactly you’re trying to build – when oftentimes, you’re too young to know.

Building could mean a number of things – building a company, building a career, a book, a lifestyle, or all at once – but we settled on the assumption that the secret to whatever you’re trying to build comes down to one basic principle:

It has to thrill you.

Caroline urges that the critical time frame of ages 18-22 must be a time for taking the time to understand what drives, motivates and excites you. Not only that, but also what bores, annoys or disinterests you. “The most successful and best leaders I know, have a deep understanding of what they are good at and what they are not good at. They a great amount of humility and understanding in that they can’t do everything. This allows them to focus on their strengths, then work with people or build teams who have complementary skill sets,” Caroline noted.

Even as you start to hone what it is that you love, the way we live and work differs from one another. Try on a few regimens for size; do you like rising with the sun and working til early afternoon? Or do you do your best work at night, and prefer to stay up past midnight to do so? Do you need to sit in absolute quiet in your own cubicle to get work done? Or, do you thrive in a coworking space, amongst other young go-getters, whom you can bond with over the nitro brew tap?

Understanding your strengths and weaknesses is key to setting a solid surface on which to build and flourish.


In just a few paragraphs, this “building” thing looks pretty easy – something that can be done in an afternoon on a scrap of paper – crossing out the maybe’s, circling the YES’s. But the truth is, the building process is teeming with traps; it’s an “all-in” process to build something that you’re truly proud of, even if you’re just building yourself.

Which means that sometimes, the free time you have looks different, and eventually – you may become quite different than who you were before the adventure started.

Those of us who went off to college experienced this at a micro level. Slowly but surely, old high school friends started to fade away just because of changing identities, perceptions, experiences. It’s okay if you outgrow people. Up until this point, many of our friendships have been made out of convenience – we took the same classes in high school, we were in the same clubs or sororities in college. We worked together. We lived next door. Crucial to building our careers and identities is choosing intentionally to rather, build a network of people “who match your mojo” (Caroline’s golden words).

Caroline urges that key to building this core network is diversity. “The more diversity you have in your network, the more diversity of thought,” she shared. But, core to this is the need to be friends with people who are going through the same experiences. She emphasized a “girl boss tribe”, because she’s recognized that many of her major career events or moments have been because of another female.

Women have played a large role in my life too. There’s something special about women coming together to uplift each other, to set aside competition and rather value each other selflessly, and seeing how we can help.

I asked Caroline her best advice for forming networks – especially with ‘girl bosses’ who are farther along in their careers, and she shared that “networking is not just asking for someone else’s time.” It cracked me up, but she also said she hates the phrase, “can I pick your brain?” – because what does that mean, anyhow? “Automatically assume that their time is 100x more valuable than yours”, Caroline advised. “Be diligent about follow-ups, and always remember to say thank you.”

Remember that the conversations you have, and the impressions you leave on those you interact with form your personal brand.


This is undeniably challenging. “It’s hard for any young person to know how they want to be known, considering they’re just trying to understand who they are”, Caroline discerned. And yet, personal brand seems so tightly wound with building a career and a network. It’s not something you can wait to create. The longer you wait to see what your personal brand evolves into, the more other people determine what it is You either become the captain of your brand and make sure all you do and put into the world is in alignment with it, or you let others draw their own conclusions.

So – where to start? Caroline advises listening to your natural calling – “What are you paying attention to? What do you admire? What brands stick out to you?”. Then, you can take it a step further – “what are these brands doing right?” You can translate these answers into what you hope to represent.

It comes down to your one-liner – just like you can explain the feel and intention of your favorite brand, you want your own brand to come across just as saliently to others. Start with your one-liner: “What do you do, and what do you stand for?”

Along these lines, I asked Caroline what all of us should strive to include in our personal brands and how we interact with others. “Be diligent,” she said. “Be that person who is so persistent 110% of the time, because otherwise, you won’t get what you want.”

It is persistence, of course, that is of central importance to us ambitious, 20-something women with a vision in our mind’s eye. It’s a wild ride, but equipped with a girl boss tribe, a clear and robust personal brand, and the persistence to weather the storms of eliminating what isn’t for you and emphasizing what is, I have no doubt the 20’s will be the most formative and wonderful years of our lives.


  • Haley Hoffman Smith

    Speaker & Author of Her Big Idea

    Haley Hoffman Smith is the author of Her Big Idea, a book on ideation and women's empowerment which debuted as a Top 3 Bestseller. She has been featured in Forbes, Entrepreneur, and the Washington Examiner, and graduated Phi Beta Kappa from Brown in May 2018. She is the founder of the Her Big Idea Fund in partnership with Brown's Nelson Center for Entrepreneurship, which awards grants to women who apply with BIG ideas, and Her Big Lash, a cosmetics company.

    At Brown, she was the President of Women’s Entrepreneurship and started the first-ever women’s entrepreneurship incubator. She speaks on topics such as women's empowerment, innovation, social impact, and personal branding regularly across companies and college campuses, most recently at Harvard, TEDx, SoGal Ventures, University of Michigan’s Ross School of Business, and more.