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Staying Outside the Lines as a Winning Strategy for Life and the Future of Law with Olga Mack

Staying Outside the Lines as a Winning Strategy for Life and the Future of Law with Olga Mack
Staying Outside the Lines as a Winning Strategy for Life and the Future of Law with Olga Mack

Get in line. Stay in your lane. Don’t color outside the lines.

My guest Olga Mack developed an aversion to lines that has shaped not just her as a person but her career journey as a tech lawyer as well. She’s joined me on the podcast to talk about how her determination to find other entry points away from standard lines has helped her level up and move through life.

In this episode of the Branding Room Only podcast, you’ll hear about how living outside the lines of other’s expectations can put you in a better, more powerful position to be successful (and have fun). We’ll also discuss how Olga’s vision of the future of law lives outside the lines that exist right now, why lawyers need to innovate by improving their visual literacy and legal communication with the average person, and so much more!

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1:00 – Olga’s definition of personal brand and of herself and why she thinks there are no boring places (or people)

5:41 – How Olga’s aversion to lines helped shape her personality through her career and why she sees Lady Justice as a snob

13:31 – Why Olga doesn’t see herself as a brand and doesn’t see it as her goal to build one

15:49 – Olga’s TEDx talks, what it was like to prepare for her first one, and an effective strategy for delivering an idea

21:41 – Why Olga wanted to write about visual literacy for lawyers and her vision of the future of law

28:56 – What Olga wants legal professionals to know as they innovate, build their brand, and think about the future of law

31:49 – The lack of separation between fun and work in Olga’s world and things she does for fun besides her work

36:00 – How Olga’s uncompromising aspect goes beyond displaying it authentically

40:36 – The #1 question people ask Olga as part of the Branding Room Only experience that only she can give others

Connect With Olga Mack

Olga V. Mack, a Fellow at CodeX, The Stanford Center for Legal Informatics, and a Generative AI Editor at law.MIT Computational Law Report, is your guide to the future of law and legal technology. As CEO, she’s a visionary leading innovation in law and legal operations, while also advising startups in the future of law and LegalTech. 

Olga’s journey includes groundbreaking roles such as former CEO of Parley Pro (now LexisNexis CounselLink CLM), where she transformed digital negotiation. With expertise in law, tech, and business, she’s a sought-after six-time TEDx speaker and thought leader featured in Forbes, Bloomberg Law, Newsweek, and more. Recognized with awards like Silicon Valley Women of Influence, she’s a trailblazer shaping the future of law. 

Explore her insights through her podcast, “Notes to My (Legal) Self,” and her upcoming books, including “Visual Intelligence for Lawyers” (ABA 2025) and “Product Counsel: Advise, Innovate, and Inspire” (Globe Law and Business 2024). Join Olga as she navigates the intersection of law, technology, and society, empowering the next generation of legal innovators.

LinkedIn

Mentioned In Staying Outside the Lines as a Winning Strategy for Life and the Future of Law with Olga Mack

DJ Charles B

The Universal Language of Law | Olga Mack | TEDxUCSB

Law as a Service for All | Olga Mack | TEDxCherryCreek

How Smart Contracts Will Change the World | Olga Mack | TEDxSanFrancisco

Sponsor for this episode

This episode is brought to you by PGE Consulting Group LLC.

PGE Consulting Group LLC is dedicated to providing a practical hybrid of professional development training and diversity solutions. From speaking to consulting to programming and more, all services and resources are carefully tailored for each partner. Paula Edgar’s distinct expertise helps engage attendees and create lasting change for her clients.

To learn more about Paula and her services, go to www.paulaedgar.com or contact her at [email protected], and follow Paula Edgar and the PGE Consulting Group LLC on LinkedIn.

Paula Edgar: Welcome to The Branding Room Only Podcast where we share career stories, strategies, and lessons learned on how industry leaders and influencers have built their personal brands. Now, let’s get started with the show.

Hi everybody, it’s Paula Edgar, host of Branding Room Only, a podcast where I talk to influencers and industry leaders about their personal brands, their reflections on their experiences, and some recommendations that they have about personal branding.

I’m super excited today to be talking to my guest, Olga Mack, who is a thought leader in the future of law space. Olga, welcome to The Branding Room.

Olga Mack: Oh, hello, Paula. It’s good to be here. Thank you for inviting. I’m so looking forward to this conversation. I think it’s one colorful lady with another.

Paula Edgar: Absolutely. I’m so excited, but just our pre-call, I was like, “Oh, this is going to be fabulous.” All right, let’s jump on in. I ask everybody this question: How do you describe or define a personal brand?

Olga Mack: I think it’s a work in progress. Well, change. Circumstances change. I see one’s brand as an evolving process of discovering yourself, your limits, and learning your skills. Olga today is a very different Olga than Olga yesterday, and yes, she is most certainly a very different Olga from 20 years ago.

Paula Edgar: Mm-hmm, I love that. Describe today’s Olga in three words or short phrases.

Olga Mack: Oh, future of law. We all have a broken relationship with justice and law. I would love to see change in my life.

Paula Edgar: Ooh, I love that. I want to jump into that a little bit more later. Okay.

Olga Mack: Small goals, small goals.

Paula Edgar: I just want to change the world. I’m with you 100%. Let’s do this. Okay. Do you have a favorite quote or mantra?

Olga Mack: It changes. There are many quotes around going with the flow. That one probably has been the most difficult for saying to do, because when we find ourselves under circumstances, we all wish we’re different, “Oh, I wish I could travel more,” or “I wish I could travel less.” This is silly things.

But I think over time, I learned to focus on what is. My passion leads me to travel a lot, and therefore I should find joy in it and optimize that experience. That’s just an example. That’s actually a very true example.

I’m now exceedingly good at traveling, and you can send me anywhere in the world, and people will say, “Oh, that’s a boring place.” I can tell you there are no boring places. There are boring people. But in any place, you can find a jam, whether it’s a restaurant, a person, a sculpture, an experience. There’s going to be something there in the middle of nowhere that you can make your travel fantastic.

Paula Edgar: I love that for multiple reasons. A, because I love traveling, I love, love, love being on the airplane and getting someplace. My word of the year is joy. You said everything that made me, I’m like, “Oh, I feel happy already about this.”

Okay. Do you have a hype song? A hype song is when they’re going to get full 100% Olga Mack, that song is playing in your head. Or if you’re having a bad day, and you need the song to hype you up, that’s the song. It’s either the same song or different songs.

Olga Mack: I don’t have a song. I love music and I can enjoy music. I myself do not have a beautiful voice and please do not, whatever is going to be next, definitely do not ask me to sing. I’m a really good dancer. Singing is not my virtue.

I can appreciate a range of music from country to pop, rock, to classical music. I’ve lately enjoyed the central collage of mixtures of classical and pop. There’s a DJ I follow on Instagram who does this really cool mix of Vivaldi. I can’t stop listening to it. It’s just amazing.

Paula Edgar: Now you’re going to have to share that with me so we can make sure we put it in the show notes because people are going to want to know. But I love that.

Olga Mack: I mean, for context, I think he’s a German guy who goes out in this really severe cold and he does his performances in the middle of the mountains and he does this really ecstatic mix of Vivaldi and other stuff that I just can’t get enough of.

Paula Edgar: Oh, I can’t wait to hear it. I do think that music is what brings us all together because of how it makes us feel so I love that.

All right, okay. Tell me, Olga, how did you grow up? Where did you grow up? How did that help shape your personal brand?

Olga Mack: Ooh, you asked that question of somebody who’s an immigrant. I believe you can’t talk to an immigrant and not be shaped by that reality. I think in my case, the big headlights is when I was around 13, we landed in what I call CandyLand, which is Silicon Valley, San Francisco Bay Area.

My life completely transformed in that I saw myself becoming an artist that makes the world a beautiful place and I decided to become a technologist to make the world a more functional place.

Eventually, I became a lawyer and my dad said, “Well, is it nicer, more beautiful, or functional that you’re going to be making this place?” and I said, “No, it’s both.” That’s the headlight.

But I was born in Ukraine, grew up in many places. My parents moved a lot throughout my childhood and I think that experience of being an outsider in many places, every language I speak, I speak with an accent and not with a perspective of a local. That is a larger scene from the day I showed up. I guess if you want to go much deeper, I’m a miracle child.

Paula Edgar: Oh, all right, tell me more.

Olga Mack: My parents were supposed to be childless. They waited and asked for someone like me for about five years and I showed up, and my entire life, everyone told me I’m a miracle. [inaudible]

Paula Edgar: I’m a big believer that we all are, but I really love that story for you. I love that story, that’s fantastic. Yes, I agree that the immigrant experience, I am the child of immigrants. My parents are from Barbados and Jamaica. It does shape your perspective on so many things that I think folks who may be born here take for granted often.

I know, there’s always a little more of a hustle. There’s like a little bit more there. I say that obviously with some bias because I’m a child of immigrants and I was a beneficiary of the hustle. I guess we can call it beneficiary. I always knew that there were eyes on me differently than there were eyes on folks who were from here.

I like asking this question because where you’re from is so different for everybody, how we answer it is so different for everybody and it does shape us. All right. Well, now share with me your career journey. You’ve done a lot. Talk about what you’ve done and how you built and evolved your personal brand along that path.

Olga Mack: Yeah, I actually imagined hustle. I joke, I grew up, I was born in the former Soviet, there were a lot of lines. I felt like my childhood was standing in lines, various food lines, really what they cut down to.

I’m now intrinsically allergic is maybe the right word to lines. When I walk into a room and there is a real line or assumed line, I have this involuntary reaction for an exit sign and alternative strategy.

I’m about to answer your question. That has been a guiding light for me in my career. I’m a tech lawyer by design. When I got to law, because I firmly believed in this concept of justice, where political refugees, you bet that my household had opinions about what justice means, and eventually why I went to law school, I got to law school, I discovered many assume they’re real lines.

“Oh, you have to go to this law school, you have to study this, you have to wait your turn, this and that,” and it’s perpetual lines that this justice system assumes. As much as I love law and I specifically left tech law, which is where in practice initially where I started, as I’ve been encountering various lines, the immigrant of me that has an aversion to standing in line, you tell me a line, I’ll look for an exit and a hustle to change the outcome.

That has been really how I ended up doing all these other things. I first went to big law, where I was told to stand in line to become a partner. Then I decided to go in-house where I no longer had to stay in line.

Then as I was a junior lawyer in-house, I was basically told to stay in line and live somebody else’s legal dream. I did not like that idea so I became the general counsel, the executive legal leader who created a new vision for that.

As I was doing that, I had this massive passion for technology and digitizing law, and became entrepreneur, and started building the future of law, and became the CEO. All of that really comes from the fact that when I see a line, I look for windows, chimneys, exit signs, anything and everything, but standing in lines.

I do think that for us immigrants, standing in line is a losing strategy. Lines are not designed for those folks who are not local and in power to win. They’re designed to keep you civil and obedient. That’s not how you optimize your life.

Paula Edgar: How do you define justice?

Olga Mack: Wow, I’ve done a whole TEDx talk about it.

Paula Edgar: That was my transition.

Olga Mack: Yeah, yeah, no, I have a view of justice. That Lady Justice should stop being a snob and she should start serving everyone. Not just everyone who’s educated, not just everyone who has resources, and certainly not just everyone who’s of a certain color and heritage.

To me, what it means will evolve into something better when Lady Justice puts on her pink glasses on and starts actually serving, actually be of service. She doesn’t have to be blind, she just has to be of service.

Paula Edgar: When you just talked about the sitting in lines and having an aversion to it, I thought to myself, “I bet that everybody who has an immigrant experience can picture a line.”

I mean, I can clearly think about lines that I’ve stood on because of my family’s immigrant experience, but never thought about how those lines literally shaped what we’ve become. I really honored that you drew the line to the line. You drew the line about lines for me because I’m pretty sure people are going to message me about this.

There’s a point in the podcast always where I know the people are going to resonate and I can feel it for this one in that I haven’t heard it articulated like that and it just really is sitting with me. So thank you for drawing that line-to-line for me.

Olga Mack: Yeah, anytime. I’ll connect dots for you. It’s the lines.

Paula Edgar: Talk to me about some of the platforms, some of the networks that you’ve been involved in to help build your brand as you’ve gone from lean spaces where you didn’t want to build everybody else’s stuff, to building your own stuff, to shaping your own thing, and in realizing that innovation in tech is the next way. What were some of the ways, organizations, people, platforms that you used?

Olga Mack: Oh, I’ve done a few things. I’ve written books, I’ve been on TEDx stage, I’ve sold companies, I’ve taught at well-known institutions like Berkeley Law. Maybe I’ll start with one thing, is that I don’t think of myself as a brand. I think of myself as an Olga who likes to show up as Olga every time because the easiest thing to do is to show up with yourself, you don’t have to think twice. I would like to enjoy that freedom.

In the process of showing up as myself, I would like to add value to people’s lives. I would like to leave my interactions, whether it’s one-to-one, or one-to-many, enriched, more educated about their options, and if none of that, at least entertained, but preferably all of the above.

Because what I realize is that, Paula, you and I will spend an hour together, or 20 minutes, and then if you have one-to-many conversations at scale, a lot of people giving you 20, 40, 60 minutes multiplied by a number of watchers, that’s lives we’re talking about, and if you don’t have value, you are wasting people’s lives.

For me, the goal is not to build a brand. For me, it’s one, to have a freedom, not to stand in line, show up with myself, and add value, and leave this world not to necessarily solve every problem it happens. But leave value behind, leave legacy behind a little better than I found.

Paula Edgar: We have that in common and I love that everything you described about not having a brand is your brand. I love it. I love it. I love it. Okay, so you talked about a bunch of things in talking about platforms, etc., and one of the things you mentioned was you being a TEDx speaker three times over. Hello. You talked about justice. What were the other two about?

Olga Mack: Spoiler alert, two more coming.

Paula Edgar: Oh, yes.

Olga Mack: I am a fan of TEDx stage, even though delivering TEDx is a lot of work, I think it’s a fantastic place if you want to start change. I mean, by definition, it’s a stage where ideas are shared. I love that concept, provided that you have an idea for sharing that will not be wasting millions of people’s lives, because it may be watched by many people.

I’ve done three TEDx talks, one about the power of technological smart contracts, one about Lady Justice being of service. I’ve dedicated a whole TEDx talk to this because I really do think that this is a fundamental glitch in our system and in the software of our legal institutions called law.

The third is universal language for justice is actually not words, it’s pictures. I think if you want to reach hearts and minds and provide value to an average person, you’re going to have to definitely stop speaking legalese and start speaking human. That’s not an English of a highly educated person, that is an eighth-grader-level language.

If you really want to move forward, that would need to be a visually digestible experience. I talked about the power of visuals and how if you travel, for example, or in the middle of COVID, pictures really dictate behavior.

Paula Edgar: That for me really resonates a lot. My father’s a photographer. I have enjoyed pictures. I love pictures and I love taking photographs for my entire life. I do think that they can tell a story and they can connect us in really, really powerful ways, to your point, that words can be barriers if you don’t understand the words in the right way.

Olga Mack: And more words don’t increase clarity. More words actually, if anything, confuse more people. But picture really speaks a lot.

Paula Edgar: Oh don’t tell the lawyers that more words don’t create clarity. Okay, so can you talk a little bit, well, this is selfishly because one of my goals is I want to do a TED Talk, what is the prep like? What was that experience like? You’re doing it more time so that means that it couldn’t have been that bad. Talk to me about how the prep was.

Olga Mack: I enjoyed. Remember going with the flow, I tried to find joy in every circumstance. At the time, not retroactively. I don’t want to go 20 years ahead and then look back and say, “Oh, that TEDx experience was really joyful.” I actually want to enjoy it as I’m going through it.

Anyway, when the first opportunity came to me to do my very first one, I actually declined. It came from the San Francisco TEDx, which is one of the more prestigious ones. I didn’t apply for it, I was invited and was invited with a specific topic in mind to talk about smart contracts.

At the time, I was very new in that field and felt underqualified, borderline incompetent to deliver that talk. That training was about a year. TEDx San Francisco gave me a coach who was wonderful, and she was holding my hand throughout the whole process. It was beautiful and I enjoyed every moment because she was such a kind, generous person.

She was very blunt in saying, “Olga, that’s not a fierce Olga I know. That is a diluted version of Olga I know who don’t show up.” Thus, the world does not need to see a diluted version of Olga.”

That for over a year, just was a very transformative experience. It was an amazing field. Actually, ironically, by the time I actually gave that talk, I was one of the more competent people in the field because it was such a new field and I grew up with that. That was a very memorable experience that involved a lot of training, overthinking, and drafting and redrafting.

I’ve since then evolved, I can now deliver TEDx at a much quicker timeline provided that I have an idea worth sharing and perfected into an art form. But in short, I think any idea is more exciting and digestible when delivered with a personal story because we are wired to love stories as my friend said, and many neuroscientists say that basically an orgasm for your brain.

If you can make an idea driven by personal experience and a story that is engaging and stimulating, that would be desirable and very effective. If you start with that and then draw three lessons out of it and a call to action, that is the basic structure without bells and whistles for any TEDx talk. If you can do that, you can deliver 10 to 15 minutes of TEDx talk that is engaging, moves the world, and gives value to the listeners.

Paula Edgar: Love it. Love it. Love it. Love it. Love it. Okay. You are also an author. Check, check, check. Talk to me about why you wrote and wanted to collaborate on Visual IQ for Lawyers. Why?

Olga Mack: Again, this is actually my fifth book. This year I’m publishing three. I’ve published four more before. I know it’s really interesting when people describe me as an author, a writer, or a speaker. I say, “Well, we’re all writers and speakers. I mean I just happened to perfect the elementary school skills and make it an art form.”

I think all of us are writers and speakers. It’s just some of us are more detail-oriented when it comes to the craft of it and care about how we show up and whether we actually intentionally continue perfecting that skill in our professional lives.

But yes, I write again for the same reason I speak and those are usually actually related when I had a TEDx talk related to visual literacy and how it really can speak across different cultures.

I’m writing a related book for lawyers so they can appreciate and incorporate visual elements in various parts of their practice so that they can be showing up more fully in daily life and their practices and more equipped. Because we live in an increasingly visual world full of icons, emojis, and communications that do not involve 12th-century or Shakespearean English or legalese.

Increasingly, your clients speak to you in different ways and increasingly use technology that has visual elements. So being a 21st-century modern lawyer requires you to be a modern human too and that means you need to be literate in judging visual stimuli around you and actually be fluent in using them in your communication.

Paula Edgar: When you describe what the future of law is, is the future of law or part of the future of law a place where lawyers understand that communication needs to be not just plain language but plain visuals too in order for them to get it?

Olga Mack: Yes, yes. You ask me about the future of law, I like to talk about the vision of the how. The vision, the why is that it has to be of service. The how, yes, one of the hows is visual, but there are other hows that should be part of it.

Paula Edgar: Okay. Are there other hows that you have been thinking? I’m just thinking of where the conversation is going, like where you want to drive it, you want people’s eyes and attention to go to, but also where you think. Future of law, I think number one, diversity is not a question mark anymore, it’s there, it’s there and we gotta figure it out quickly.

Also, technology and AI and also thinking about hybrid is the new state of being. We’re sitting here like those things are a part of the future, whether by will or won’t, it’s going to happen. Are there other things that when you think about where you want us to go as your vision that I didn’t talk about or that you want to talk about more?

Olga Mack: Yeah. It’s interesting. Again, up service, the main premise. I think visual is part of it, technology is a big component of it. As I alluded in the beginning, today our legal system really selects educated, highly resourced, skewing, certain color folks.

This is not a political statement, this is just a description of facts. That underserves like 95 plus percent of the population, not necessarily indigent, but just a massive number of people underserved.

The only way to reach those folks, educate them, and to give them an opportunity, give them an opportunity to do right things in life is by meeting them where they are, giving them education that they can consume because most of us are capable of making good choices in life, provided that we are educated in a timely manner in the language that we understand.

I don’t mean English, French, Cantonese, or whatever. I mean in the way that we actually can comprehend, understand the importance and be part of the conversation, and technology is a big part of it. Helping lawyers to be of service for really complex cases is definitely important.

Distributing information and giving tools to the rest of the population that probably did not need lawyers, but make legal decisions or part of legal events on a daily basis from various contracts assigned to marrying, marriage is a legal event, you really feel how legal it gets when you get divorced, which is too late to make various decisions, for example, opening a bank account is a legal event.

You really feel how legal it is when you go through bankruptcy, none of that information, I don’t care how wealthy you are, educated you are, when you open a bank account, most people do not know what they just signed. I as a lawyer have no idea what I sign.

Paula Edgar: And there’s a stack of paperwork.

Olga Mack: And there’s a stack of paperwork. There’s a wall of paper. Your insurance policy, have you read your insurance policy?

Paula Edgar: I have actually read my insurance policy. I’m proud to say that, yes, I have read my insurance policy, but to your point, because I was making sure that something that was happening wasn’t just going to be an issue, like, we had a storm coming, I needed to make sure we had flood insurance, all of those pieces were in there. I think your point is right, that we get it, the legal piece of it when the stuff hits a fan.

Olga Mack: Yeah. [inaudible] damaged. But if you were educated at the point of purchase, I mean, are you capable to make the right purchasing decision if you have full information? You bet I am.

Every time I buy a shoe, when I have full information, I buy the right pair. I’m completely capable of buying the right stuff provided I’m educated at the point of purchase. If I can buy shoes, I can buy insurance provided that I’m educated.

Paula Edgar: Agreed. I mean, it’s accessibility. I love that you’re bringing up it as a point. If you think about the people we navigate with, the legal professionals, what advice, given what you know, what you’ve seen, would you give to folks who want to be more innovative, want to think about the future of law, and also want to build a brand?

What’s coming up for you in terms of things that you would want to tell the people? What’s your impact going to be in terms of your voice in this moment about what you want them to know?

Olga Mack: Oh, that’s a lot of questions.

Paula Edgar: I know.

Olga Mack: Maybe I will answer some.

Paula Edgar: Get to the one you want.

Olga Mack: That’s really interesting. I think starting with self, what’s important to you, showing up as yourself is more important to some than others. It is extraordinarily important to me.

I’ve tried many times in my life to fit into a box to show up as a deluded version of self. It turns out I’m incapable of doing it. This gene of people-pleasing is just completely missing. It’s not going to show up in my lifetime. I can mitigate the damage or I can just go with that path and make the most of it.

For me, it’s very important. It’s not going to be most important for you. Understanding the value, the values that you care about and your why, I think it’s very important. I think the second thing, as I mentioned, is to have that vision, that anchoring vision. I think the why is always more important than who. Those two are definitely more important than what and then those three are more important than how.

If you have an articulated why, it’s a much better statement of a vision. I joke if you are a how-to-my-why, we’re going to be best friends. I mean it to humans and I also mean what you call platforms.

If the tactics give you a how to your why, then that’s the right place. If a book gives a how to your why, then it is the right place. Meaning you will reach the right audience, whether it’s a one of many, to make progress from point A to point B. Whatever your why, if you have clarity and make best friends with the how, when you use the how, that brings me to the last point, give value, so that whomever you engage with, whether it’s one or many, or however long, from five seconds to hours, they come out without their life wasted. If you can do that, I think you can create an impactful life worth living.

Paula Edgar: My favorite word, impact. Impact, impact, impact. Okay, so what about the fun stuff, Olga? What do you do for fun?

Olga Mack: It’s funny, it’s interesting that you separate fun from this. To be completely honest with you, this is fun. It’s interesting because we as lawyers are trained to have an analytical analysis of laws and facts, and we are trained to bifurcate and trifurcate, and beyond issues, like separate things, laws from facts, life from laws, business from laws.

Oh, this is a business question and this is a legal question. That’s not how humans work. Humans do not bifurcate their analysis. You go to a business owner and tell them to separate their business from their legal applications.

Heck, let’s make it even more relatable. Go to somebody who’s getting divorced and may not like their ex-spouse or soon-to-be ex-spouse and tell them. But the purposes of the settlement is to make a rational decision to separate law from life. Good luck to you and that conversation. That’s not going to happen.

Paula Edgar: Right.

Olga Mack: This segregation of fun and work, I think I’ve done that before. It took me about 15, 20 years to figure out that this thing that I was doing for fun, which is future of law, the writing, speaking, and advising, I could actually be paid for this. That actually could be my job.

I mean, I could be paid to show up to have fun every day. That realization was very important for me. It only took me a very steep learning curve sometimes, took me about 15 years. It’s still unbelievable to me, but I actually don’t separate it.

I know how to have fun in other places. I thoroughly enjoy all kinds of things. I bring to life anything on the wheels. If you give me somewhere between roller skates and bike and car, I really enjoy that experience. I love speed a lot.

I like putting myself on objects that move and try to balance. It really gives me a lot of joy to challenge my physical body. I have two teenagers who challenge me in many ways and my definitions and the way I look at the world from valuing more virtual goods to having a much more sophisticated view of race and gender than like I’m still a student of that I really enjoy spending time with them.

Again, I’m a trained artist. Remember, at some point in my life, I thought I would be an artist. I have a formal training in art and sometimes I like to create. There are other things I do for fun, but I definitely do lots of good day fun from work as much as I used to. Still work and drive it.

Paula Edgar: Agree with that. I love that as a thing. I believe in joy in everything we do, even when it doesn’t necessarily feel joyful to find the joy in it. But I definitely will say, there’s something that I do for fun, just on their own, they have nothing to do with work.

But I love it when they intersect though. I do love to have to work with people who are fun. I love to do things that are fun while working. I do get that. It doesn’t need to be bifurcated, but unfortunately, too many people do see it as silos, like “Here’s my fun me, here’s my work me, and the twins, they shall not cross.” I’m like, “Oh, no, well, if you work with me, they’re going to cross because I love a joke and I love to smile,” and so all of that, fabulous.

Okay, so I ask two questions to everybody on my podcast, one is your stand-by your-brand piece and I think I’m going to be able to guess what your answer is, but I’ll ask you.

Olga Mack: No, I want to know, what would you guess?

Paula Edgar: I’m going to ask the question and I’ll tell you what I think you’re going to say. Okay, so the question is what is the authentic aspect of your personality in personal brand that you will never compromise on? I think that your answer would be in justice and being future-forward thinking, so.

Olga Mack: Yeah, and for me, also showing up is nice.

Paula Edgar: Authenticity, authentically doing that. I love it.

Olga Mack: It’s beyond authenticity. I come to see that and I often feel it’s an overused term. I think it’s a little bit beyond authenticity. Really truly, what I mean by that is I’ll give you an example. When I imigrated, I was 13 or so, I did not speak English.

It started as a joke that people asked me what I wanted to be, what I wanted to be when I grew up, I would say, “I want to be a lawyer,” except everybody knew that I didn’t speak English and everybody would just stare at the 13-year-old or 15-year-old when she says that, either with an accent or a really broken English.

I initially did it because I just wanted to create this uncomfortable awkward moment and stare and see you struggle. Because to be a lawyer, you really ought to be born here because English is the tool that you use to win cases, yet this girl who is adorable tells you that she wants to be one and you don’t want to be the person who tells her no.

So you are standing there in the internal conflict, like, “That’s cute, not realistic, but I don’t want to be the one telling her that.” I’ve done it many, many times, and then at some point, I would just have this conversation with my dad. I was like, “You know, Dad, I noticed people cannot imagine that I become a lawyer.” My dad said, “Olga, have you also noticed that people don’t have imagination?”

Paula Edgar: “Yes, dad. Exactly that.” Exactly that. I mean, again, when you think about the experience growing up, it’s who and the values and the messaging that you get from parents too, because if it was, “No, you can’t be a lawyer,” as opposed to “You could be whatever you’re going to be like,” we can get to that space, that also gives you a freedom to be more you.

Olga Mack: Yeah, that experience happened when I wanted to be an artist by the way, because I actually was not skilled at all. In fact, so much so that my mother, in Ukraine where I was born, they used to rank your kid’s art from best to worst when they displayed to the parents and mine was always first from the back, meaning that I was not particularly skilled at drawing.

My best friend decided to go to art school and I went to my mother and I said, “You know, Mom, I would like you to pay for my art school. I’m now going to spend 45 days after school for 35 hours perfecting this thing of drafting, painting, sculpture.”

My mom said, “Oh, you sure you want to do that?” I said, “Yeah, that’s where my best friend is going. We’d like to spend more time with her.” It’s really interesting. They sort of went with it. They encouraged me to go and pay for the lessons and were cheerleading.

I think all of us in the process learned that it was actually a learned skill to paint, to draft, to sculpt, to do all kinds of things. That lesson that most skills that you’re not born with, you actually learn, it was very powerful.

Paula Edgar: Yes, I’m remembering my art class in high school. I’m sure that if my art teacher listens to this podcast will be like, “Paula, you were at the back of the line. You did not learn in fact.”

Olga Mack: But that means if you are in the back that everything you do is a miracle. I can’t get any more than that.

Paula Edgar: I was ready for progress. That’s exactly, I love that perspective. Okay, so in closing, the last question I ask the guest is the term Branding Room Only is a play of the term standing room only, which I want you to tell me what is a skill or an experience about you that people would stand in a room, standing room only to see your experience about Olga Mack?

Olga Mack: By the way, we just came back to the line.

Paula Edgar: We did.

Olga Mack: You just ask me, what would people stand in line to hear Olga speak about?

Paula Edgar: They don’t have to be in line. They can just be standing.

Olga Mack: Standing room. Very interesting. I think the number one question people ask me is how you pivot. I’ve never had the same job twice. It’s partly because of this perpetual looking for a place with no line and creating opportunities and showing up on self.

Partially because I’m a woman of many interests and I think that talents can be developed, learned, and built. I really have enjoyed the process of doing it. So the number one question people ask me is either specifically how I generally transition and pivot or how I pivoted from one place to another that people actually consider doing today from big law to in-house for example, career from being an attorney on a team to being the general counsel, to then being a strategist, to then being a CEO, to speaking in a TEDx talk, how to do it more than once, those things, the pivots. I think I at this point have mastered the art of pivots.

Paula Edgar: Well, I love that because I do think a skill set in terms of building your brand, it’s iterating and pivoting, one necessary or one new strategy is that you want to do something different, which I think everybody who knows listening to this knows that I love that. I love hearing people’s stories because they may think that their career is going to be a straight line, but it really never is. It is a lot of hills and valleys.

With that, Olga, I want to thank you so much for being on the podcast and telling your story about not being in the lines, being outside of the lines, because that’s where you belong. You want to not be in lines. You’re welcome to come back at any time to talk about whatever you would like. Everybody, share this with a friend who shouldn’t be living in the lines either. We’ll talk soon. Bye.

Olga Mack: Thank you so much. Bye.

Paula Edgar: You’re so welcome.