Almost exactly one year ago, I started this blog after a sleepless night during a family ski trip. I spent all night, laying in bed, staring up at the ceiling, mourning the rapid passage of time and trying to figure out how to spend as much time with my kids while they were still little while still earning an income. Twelve months later, I’m spending more time with my kids than I ever have before and loving it. (Alas, the income part of that plan has been a little slower to develop!)

One of the rabbit holes I’ve gone down is the world of personal branding. My work as a fund raiser required me to be likable to donors, many of whom I socialized with, so I knew my professional success was directly linked to my social standing as a trustworthy, friendly person. But as a blogger, I have to think about my personal brand in a new way. I have to learn how to communicate my personality, values, ethics, sense of humor, style, and soul to people through the internet; to people I may never meet in person (although, I’d very much like to meet you if I haven’t!)
I sat down with my friend, Tim O’Brien, who is – among other things – a personal brand specialist, to help me understand exactly what a personal brand is, why it’s useful, and how to cultivate one.
If you’re wondering what use personal branding is to you, you’re not alone. Until recently, I was repulsed by the idea, believing it to be a dubious, contrived image you projected out to the world, meant to distract people from your flaws and minimize your humanity. But it’s quite the opposite. It’s a powerful process of self-discovery that requires courage, humility, and a sincere hunger for growth. (And if you can laugh at yourself, that helps speed things along.) I would argue that if you’re not thinking about your personal brand, you’re very, very far from reaching your full potential as a human and, therefore, you’re missing out on a lot of joy.
Don’t agree with me? Read what Tim has to say and decide for yourself.
First, tell me about your career background. How did you get into personal branding?
I was practicing law in New Jersey, but I didn’t really enjoy it. So, I went to an acting class in New York and the guy who was teaching the class had this thing called “The Hour of Power” where he spent the whole time telling us “You can be anything you want to be.” It’s a very aspirational point of view and it opened my eyes to Personal Development. You know how something just resonates with you? I realized it was something I’d always been interested in, but until then, I couldn’t name it. I’ve always believed you should do what you love and find a way to make money doing it, so I just decided, “I’m going to get into this business”, and that was it.
So, you take this class, you’re totally inspired, and then what?
The biggest breakthrough for me was realizing that I wanted to get outside my comfort zone. I was very risk averse at the time. The value system I was raised on was very conservative – I don’t mean politically – and we were taught to be cautious, so there was always this tension within me between the way I’d been raised and the person I wanted to become. I wanted to experience more from life, I wanted to take chances, and to go places. And that part of me was stronger than the part of me that wanted to protect myself.
At first, my parents weren’t very happy. Their son graduates from Georgetown law school and is now telling them he wants to leave and become and actor. But it was all part of the process. They didn’t realize I had this inner-tension within me.
For the record, you’re not an actor.
No, I’m not and I didn’t jump right in to personal branding; it’s been a process of evolution. The first thing I did was I made a cold call to a company selling a tool for hiring people and they hired me based on that call. I didn’t know any better, so that first year I made 7,000 cold calls to the wrong people. I was calling people I thought would be really passionate about the product and would be really into what I was selling instead of the decision makers. But it’s okay because I got to hone my skills.
You’re lucky you were able to learn this about yourself and make this change before you had a wife and kids.
Very much so, because it was very messy.
So, how did you get into personal branding, specifically?
I’m completely self-taught. I always tell people I went to law school to learn how to make a living, but I went to Barnes and Noble to learn how to start my business. One thing I always knew was that I had to have a niche and I was always looking for what that was, so I started a program called “Rainmaker You” which was all about teaching people to get outside their comfort zone, take chances, take risks, and expand their boundaries. Ultimately, it’s about teaching people how to have relationships.
At that time, I knew that in order to have great relationships, you needed to have a good personality and be likable, but I still didn’t know it was called “personal branding”. But as soon as I saw the term, I knew that was what I was doing.
How do you define “personal branding”?
It’s simple: your personal brand is the word or phrase you want people to think of when they think of you.
Everyone has a brand. It’s not optional. When people think of you, a phrase, image, or word comes to mind. It’s an intentional set of actions to redefine how you want people to think of you.
In America, we love comeback stories. Think of all the people who have bad experiences, and we end up loving them. They redefine themselves. They reengage. In fact, we usually end up liking them much more than we did before.
George Foreman is a great example of this. He was a mean, mean guy. He was bad. And he prided himself on being that way. But he had an experience in his life that changed him. He decided, “I’m gonna be nice”, and all of a sudden, a whole set of new opportunities opened up to him.
You get to decide what you want your brand to be. But what’s really important to know is that no matter how much money you have or what your title is or how great you think you are, you can’t force people to like you. This is a big problem for some people at the top of the food chain. They think people love them, even if it’s not true. People like that you write their paycheck!
Is that who you market to? C-Level people at the top of the food chain?
I like to work with people who are already successful because it tells me that they’re already motivated. But they have to have a desire to grow and to change. Genuinely. When they’re at the place where they’re saying, “I don’t like where I am. I’m in a rut,” those are the times when growth really happens.
But I also encourage my clients not to discount anyone. Think about the receptionist at an office. Don’t you want her to have a fantastic personal brand? Because she’s going to reflect upon the company, good or bad. So I want to work with that person, too, if that’s what’s going to help everyone be more successful.
Does this apply to non-professional people? For example, does a housewife with no career aspirations need to think about her personal brand?
I always say to my dad, “Dad, you gotta work on your brand.” He’s eighty year old. He’s thinking, “why would I work on my brand?” What I tell him is, “do you want your grandchildren to say, ‘oh man, I gotta go to grandpa’s’ and they do their duty begrudgingly and get it over with? Or do you want them to get excited about seeing you and say, ‘I get to go to grandpa’s today and I’m really looking forward to it’?” It comes down to likability. When the grandkids are with him, do they get to do fun thinks like work in the backyard or take a trip to the store? Or are they just doing it because mom says they have to do it? His brand should be attractive to his grandkids because he cares about them and wants to have a good relationship with them. And he wants them to remember him in a positive way when he’s not around. Your brand should be attractive to people.
If you’re a parent, you don’t really have to be likable to your children. You can order them around and they have to do what you say. But that’s going to influence the kind of relationship you have with them once they become adults. So – yes – a mother who is home raising her kids needs to think about her brand as much as anyone else if she cares about the quality of her relationships with people; if that’s important to her.
Mothers are the best brand managers. She tells her son to comb his hair. He says, “it’s combed, ma!” No it’s not, and she makes him comb it again because she doesn’t want him going out looking like a mess. She doesn’t want people saying, “what’s going on in that household? Is anyone in charge over there?” She wants her kids to put their best foot forward because she wants the most for her children. And you want them to reflect well on the family. Moms nurture that better than anyone else.
My wife is a good example. Every time we’re at an event for the kids’ school, she’s on me like my mother, telling me, “now make sure you say ‘hi’ to Tracy” or “make sure you say ‘thank you’ to Kevin for having Caitlin over last week”. She’s minding my brand because she knows I reflect upon her brand.
The first time I heard the term “personal brand”, I was very turned off. It sounded fake and contrived. How does someone keep their personal brand really authentic so that it’s not just about image, but that it’s about putting forth the best version of yourself?
You hit the nail on the head. Branding is so much deeper than image. It’s not about your image; it’s about who you are as a person.
I’ll give you a good example. Do you remember Rock Hudson? He lived a lie and it was sad. I’m not criticizing him, but that was an image. Your brand has to be an authentic reflection of you.
If you tell me, “Tim O’Brien, you need to tone it down. You need to be more demure”, it’s not going to work. I’ve been shaped by the books I’ve read, by the people I’ve met, by the values my parents instilled in me, by the church I attend, by the friends I’ve kept, by the places I’ve visited. I’ve been shaped by all these things. That can’t be undone. But by the same token, I can’t just say, “this is who I am and that’s the end of the story”, because if I do, I’m not going to have a lot of friends and I’m not going to be successful in life.
I don’t ask my clients to change their personality. What I ask them to do is to have a core identity that is organic and reflects who they are. But you have to behave intentionally when you’re out in the marketplace. I’m not interested in a guy who people think is a wonderful guy who’s super polished, but behind the scenes, he’s an alcoholic or a philanderer or he’s abusive to his wife. That’s incongruent and it’s a lie. Unless he genuinely wants to change, I can’t help him.
Your brand can’t be too much effort. Without naming names, there’s a very popular, very famous basketball player who, I know from people in the business, is not a great guy. He’s a phony. He shows up late, he makes people wait around for him, he doesn’t treat people well. He’s unprofessional and people who work with him don’t enjoy it. He’s manufacturing an identity.
By contrast, Shaquille O’Neil is an extremely likable guy. I have a friend who was doing an interview with him and a there’s a knock on the door. It’s these little kids from the neighborhood, asking him to come outside and play with them. And he says, “hold on, Guys. I’ll be out in 15 minutes”. It’s authentic. That’s why Shaq is so lovable. His brand matches who he is inside.
Here’s another example: Alex Rodriguez and Derek Jeter. Both good looking men, both multi-millionaires, both All-Stars, both MVP’s, both thought of highly in their industry, both minorities. One is loved. One is hated.
No athlete sells as much merchandise as Michael Jordan. No active player comes even close. The guy’s been retired for 15 years! But his brand is so strong. I don’t know how authentic it is, but he’s protected his brand well and he’s not out there pretending to be something he’s not.
People with money and power can project a certain image, but why don’t you just choose to be who you are?
There’s a great author, Leo Buscaglia. He’s a professor at USC and has had numerous books on the bestseller list. He wrote a book called “Love” and in the book he talks about being a little boy, going home in east L.A., crying to his grandmother because kids were picking on him. And his grandmother said to him, “Look, you need to decide what you’re going to be. Are you going to be an apple, an orange, or a pear? Whatever you decide, be the best apple, orange, or pear you’re going to be. But remember: no matter how good you are, some people just don’t like apples, or they don’t like oranges, or they don’t like pears. That’s life.”
That’s what’s important in branding. Run the risk. Don’t offend people. Don’t be mean. But run the risk of not being all things to all people and realize sometimes people won’t like you because you’re not their cup of tea. The greatest thing you can do is be consistent.

This is something I’m thinking about a lot these days with my blog, with my presence on social media. It’s harder than it sounds! Learning from other bloggers is one thing, but there’s a strong temptation to mimic successful bloggers. A friend of mine gave me some very good advice early on; he said the best bloggers have an authentic voice people can relate to. I have to trust that my unique voice and personality is going to draw people to me, even if it means alienating others. It’s a big risk. Some people will reject me and that’s hard. At the same time, I’ve felt some pressure to limit myself by picking one particular lane. People have told me “be a Mommy Blogger or be a Style Blogger, but don’t be both”. But I like so many different things! I don’t want to have to pick one, and yet, I also want to create content that’s relevant and attractive to people.
When you help someone determine their personal brand, where do you begin? Do you start with what their current brand is and how they want it to change? Or do you just start with what a person wants their brand to be? How can I discern whether I’m avoiding being an apple, an orange, or a pear, or if being interested in a lot of different things is part of my brand?
I don’t really care what a person’s current brand is. If it’s not good, I don’t want to be tainted.
The first thing I tell people to do is to list every attribute about themselves: I’m from Colorado, I like fashion, I like raising money, I’m outgoing, I’m a good public speaker…whatever it is, you have to put everything out there because whatever they are, those are the qualities you already have. Those are your legos; your building blocks.
Then, what you have to do is to combine those building blocks into categories that produce an attribute because your brand is your attribute; it’s the word or phrase people think of when they think of you. If I say, “Tracy Smith is…”, how do people answer that question? And by the way, your brand can be really simple. The answer can just be, “Happy”. Tom Hanks has made a lot of money and built a hell of a career just being a nice guy.
Some days you’re going to be really passionate about what you’re doing and some days you aren’t. That’s not bad. You love your husband, but you probably don’t feel the same passion you felt when you first met and fell in love; at least, not all the time. That’s okay. That doesn’t mean it isn’t still love. At the end of the day, you have to be the real you. So, maybe you’re running the risk of trying to be all things to all people, or maybe you want to cast a broad net. There’s 325 million people in America. You can be a specialist in casting an extraordinarily broad net!
I teach people to specialize and focus, but I’m always mindful of who they are, where they’re performing their business, and who they’re trying to reach.

I once met with a marketing guy who showed me a brochure for “The Gay Man’s Therapist.” And I thought, “that’s a brilliant idea.” He could have said, “The Gay Man’s Therapist in West Hollywood” and that would have been more specific. He could have said, “The Gay Man’s Therapist in West Hollywood on Santa Monica Boulevard between Doheny and La Cienega.” He’d guarantee he’d only get the clients he wanted.
But then I looked down and he had all these other brochures: The Valley Therapist, The South Bay Therapist. He went from being a specialist to being an octopus.
Your brand is not what you do for a living. What you do for a living is where you demonstrate your brand, where you show off your brand. That doesn’t mean what you do is irrelevant. We may know a person because of what they do, like in the case of a celebrity. But we like a person because of their brand.
Give me an example of someone whose brand is very obviously about who they are and not what they do for a living.
Father Greg Boyle. We don’t really think of him as a catholic priest – or at least I don’t. But he says mass every day at Sacred Heart on Sunset Boulevard. We don’t see him as a local pastor. His brand is Unconditional Love. People ask him all the time if it makes him mad that people take advantage of him and he says, “absolutely not. I’m here to give away my advantage.”
Being a catholic priest is how he became the Father Greg Boyle we know; it’s the platform that allowed him to live out his brand promise. But that’s not necessarily how we think of him and we like him because of his brand – not because he’s a catholic priest.
What’s the end goal of a personal brand?
For me, it’s really simple: it’s to build awesome relationships so that my life is really rich. I get to have great friends, I get to laugh, I get invited to participate in things, I get to go to interesting places.
I’m so grateful that I have a place to go and people to talk to every day. The caliber of those relationships is directly reflective of the caliber of my brand. The better my brand, the more awesome people will want to be my friend. That’s what it’s all about for me. For someone else, it might be something different. But it’s always about relationships and what you want to experience in your relationships, what kind of relationships you want to have.
Everything you do either takes away from or adds to your brand. For some people, it’s very natural and easy. Other people have to work harder at it.
When I first start working with someone, there are some obvious changes. They may change the clothes they wear, the way they talk; they change some obvious habits. But building a brand is an ongoing process of tinkering and a lot of people don’t get that. They quit the process after a while because they’re not getting the same feedback; people don’t notice the ways they’re changing and growing.
Building your brand is like building a house. Initially, everything you do gets noticed. You build a bathroom, you build a kitchen. But then you go to the next level; you paint the children’s rooms and add some crown molding. People may not notice, but the house has improved. That’s what it’s all about.
It sounds like it requires a lot of honesty and the courage to look at some things about yourself you may not want to see.
Have you ever heard someone say, “my brand sucks. I’m a jerk”? Nobody says that, but you and I know, some people’s brand sucks and they’re jerks.
Men’s Health Magazine did a survey and asked men how many of them think they’re good looking. Eighty percent of the respondents said they think they’re very good looking. It’s not possible! They’re not willing to look at themselves objectively.
That’s the starting point. You have to ask yourself if you’re wiling to have an honest conversation about who you are and how others perceive you. Strip away title, money, education, until you’re raw. People make up their mind about you in a quarter of a second, so you might as well think about how you can be very intentional with that opportunity.
When I do seminars, I hand out index cards to everyone in the room and I’ll call someone up and ask everyone in the room to write down the word or phrase that comes to mind when they see that person, even if they’re seeing them for the very first time. Some people freak out when they hear what people write down. They can’t believe that’s how people perceive them. But I say to them, “you just got the greatest gift in the world!”
But you also can’t live your life according to that. If you get one outlier and the rest are similar, you’ve got to go with the ones that are similar. Let it go.
Be an apple, or be an orange, or be a pear. But not everyone likes all those things.
That’s exactly right. You can’t please everyone and you have to be okay with that. You can’t take it personally. If they don’t like you, so be it. At the same time, it’s not okay to blow everybody off and dismiss what they’re saying about you and how they think about you. Building your brand requires bravery, and it’s a risk worth taking because it will give you a better life.
Thank you so much, Tim. You’ve given me a lot to think about. If someone wants to learn more about personal branding or about you, specifically, what’s the best way for them to do that?
I have a lot of tools on The Personal Branding Group website. And if they still don’t see what they’re looking for there or if they have questions, they’re welcome to email me personally at tob@thepersonalbrandinggroup.com and I would be happy to recommend additional resources.
You can also check out Tim’s profile on LinkedIn or follow him on Twitter at @tobrainmaker. (Full disclosure: as with many of my friends, Tim and I respectfully disagree on politics!)
Great job Tracy! Good luck with the new venture, I know you will be great and I’m going to love following you.
Thank you! That means so much!
I love that you’re pursuing this! Stepping into authenticity and your personal brand can be a daunting and scary path. Especially when they veer from the status quo. I look forward to following along on your adventure.
Thank you, Courtney! I’ve enjoyed following yours (on IG, at least), too!