Smart, talented, ambitious women still don’t face a level playing field when it comes to reaching their full potential in the workplace. Advice to My Younger Me: Career Lessons From a Hundred Successful Women is the guidebook you need to change that. For over 20 years, award-winning career coach Sara Holtz has been helping women advance in their careers.

Since creating her top-rated podcast, Advice to My Younger Me, she has interviewed more than a hundred highly accomplished women about the career lessons they’ve learned along the way. Now, she distills their best mentoring advice into nine specific steps you can take to get to the top.

Benji Block: Welcome to The Author Hour Podcast, I’m your host Benji Block and today I’m honored to be joined by Sara Holtz, she’s just authored a brand-new book, Advice to My Younger Me: Career Lessons From a Hundred Successful Women. Sara, we’re so glad to have you here on Author Hour today.

Sara Holtz: I’m delighted to be here, Benji.

Benji Block: Sara, can you quickly just provide some context for us on your background and why you felt now is the best time to write and release this book?

Sara Holtz: Great. Depending on where we want to start, for the last 25 years or so, I have been coaching and training women lawyers about how to succeed in the workplace. When I retired — or attempted to retire — I started a podcast, which is called, Advice to My Younger Me, where I interview very successful women about the advice they wish they had received earlier in their career.

There was so much wisdom shared, we’re now up to about 130 episodes. Women from just all different backgrounds: authors, therapists, management consultants, lawyers, tech executives, just a very broad range of industries and experiences. There was just so much wisdom shared in that, in my conversations with those people, that I felt like it really needed to be shared more broadly.

I know that nobody’s going to listen to 150 podcast episodes, fascinating as they may be, so I tried to distill the themes and it turned out that there were really nine themes that came through these various interviews with people coming from very different backgrounds and industries, experiences, et cetera. That’s what this book is, is that I hope that it would provide the information that’s been shared with me so graciously into these nine themes that a reader can read in relatively short time and take away that learning and apply it to her own life.

Benji Block: Obviously, translating a hundred-plus episodes of a podcast into a book format, that can be quite a project. How did you see these nine themes sort of develop as you were looking to make this into a book?

Sara Holtz: Well, it turned out that when you listen to the conversations, there were themes that came back time and time and time again, so I’ll give you one example of that; the need to take risks, to have a successful career. People talked about it in many different contexts, people talked about it who were management consultants, people talked about it who are magazine editors.

That became one of the themes, which was that you need to take smart risks. And so, maybe not surprisingly, again, these are all very successful women, there were some very common threads about what they wish they had known earlier in their careers.

Taking Your Career To The Next Level

Benji Block: As you work on this project — clearly, even by the title, we kind of have an idea that you’re talking to your younger self but — who are you imagining in your head as the ideal reader for this book? Is this someone that this book is really going to help take their career to the next level?

Sara Holtz: Great question. My target reader is a woman who works in a corporate environment or a professional service firm between probably the ages of 25 and 40. Although, I have to say that when I set out to both do the podcast and write the book, that was the target market that I had in mind, it turns out that women who are older and women who are younger have told me that they’ve really gotten a lot out of the conversations as well.

Benji Block: That’s great. Well, let’s dive into some of the content here for the next few minutes and I’m excited to talk with you about this. One of the things that you mentioned is that as a business lawyer and as a C-Suite executive at Fortune 500 companies, you were faced with a number of challenges that, at first, you were unsure of how to deal with.

You talk about, “How do I get credit for the work that I’ve accomplished? How do I navigate being interrupted by male colleagues?” Tell me more about those early years and what you experience and going, “Man, I wasn’t really prepared for this.”

Sara Holtz: Well, most of my career, I was the only woman in the room. I graduated from law school in 1975, believe it or not, and it was very unusual for there to be a woman executive in a corporate setting. I experienced plenty of experiences because of that. Some of them were completely unconscious in terms of the people who were exhibiting the behavior and some of them were pretty conscious and designed to intimidate or to make me feel like I didn’t belong.

Benji Block: Do you have a time that really sticks out to you or an example of one where you go, “Man, I need to figure out how to approach this differently”?

Sara Holtz: Well, I mean, there’s hundreds of examples but one of them, I guess, that was pretty dramatic was when I had my first child, and I didn’t know how to navigate the workplace as a pregnant woman and I didn’t know how to navigate the workplace as a mother. An example of that, which I’m not at all proud of, is at this point, I was a vice-president at a Fortune 500 company. I was the general counsel of the company. I didn’t have any pictures of my children in my office.

The reason was because I didn’t want to go there with people. I didn’t want them to be confused about my role as the chief legal officer versus my role as a mother. I look back at that and as I said, it’s not a proud moment or proud action on my part because I think it was not very supportive of other women who chose to make a different choice and who maybe were in a less powerful position and therefore could exert kind of the power of the position to have people take them seriously.

If I had to do over again, I would have pictures of my kids all over the office to demonstrate to people that you could be both a serious professional and a caring mother but that’s an example of something that was really difficult to navigate because I just didn’t know how to balance motherhood and my professional role.

Benji Block: Wow, yeah, that’s a good tangible example and something that I never would have even thought about honestly, so thank you for sharing that.

Sara Holtz: Hopefully, women no longer have to navigate that. There’s lots of mothers in high-powered positions in the workforce but at that time, I really didn’t have any role models or peers to turn to for advice about what I should be doing.

Benji Block: Well, I love that this book kind of steps in as an outlet for one of the ways that people can, we can, see progress happen, you know? That’s how it happens generation to generation with people like you stepping up and passing on these types of messages. I really appreciate you taking the time to do this and outlining these nine steps.

Sara Holtz: Well, having said that, I have to say that there’s not as much progress as I might have predicted, let’s say, 30 or 40 years ago. In fact, the word I use in the book is that there’s been glacial progress. Just as an example: for quite a long period of time more than 50% of the graduates of law schools are women. Yet, the most powerful position in a law firm, which is being an equity partner, that number has barely budged in the last 10 years. 

When we look around and we see a few women CEOs and women who are vice presidents in companies, partners in management and law firms, all of those kinds of things, the reality is, we’re nowhere near having half the people in the C-Suite be women, and that progress has been glacial and I think the pandemic has actually only exacerbated that situation with women having — not only doing their jobs and being parents but now being teachers or daycare providers or all the things that have the burden, which has fallen disproportionately on women.

Benji Block: I think there is so far to go and clearly, I mean, even just laying that out, we could get into a number of what you think contributes to that. I think what would be great for the next few minutes, let’s dive into maybe some practical, actionable steps and hopefully as you set out to do, let’s make an impact for some of these women and hopefully we’ll continue to see change here year over year but I want to start here, I want to start with the first step that you write about and it’s to be the architect of your career.

There is this, for whatever reason, there is this way that people can take this kind of passive approach to their career path, waiting for something to hit them. What do you see being the main reason that women may take a passive role in their career?

Sara Holtz: It’s the easiest thing to do. I think men take passive roles in their careers as well. It just has less dramatic, negative impact for men. By the way, I want to go back to a word you used in asking this question, which was about the impact that this book might — hopefully will have on women.

That is actually exactly why I wrote this book. I did want to have real tangible impact on women’s careers. I wanted to give them some clear, actionable advice, practical advice about what they could do to be more successful.

We’ve been waiting a long time for the workplace to change and as I said, that’s been much less rapid than would be — [than] I would like to see. So this book is really written to have an impact on individual women in their careers.

Benji Block: I think that’s so good. I think we need to hit it from both angles, right? This is one that you’re jumping in on is going to have a great impact. When you’re in a frame of mind that has been maybe passive for quite some time because it’s more comfortable there, it can take something to jump-start you, right? To move from passive to some sort of momentum on your own terms. What have you seen work for women as they try to jumpstart defining what they want in their career?

Sara Holtz: I think it’s recognizing that they do need to have control over their career and that they need to take the steps to make their career be what they wanted to be. It’s kind of a mindset game as much as anything else because, once you have the mindset that, “It’s my career, I need to be responsible for how it unfolds”, then all of a sudden, the path opens up.

You begin to see, I have to ask for that assignment, I have to ask to be included in that team, I can’t just sit here and wait for that to happen. It’s not that there’s any specific actions that people need to take to own their careers, it’s recognizing that they do need to own their careers and then, as I said, once you’re clear about the fact that you can’t just rely on a mentor or sponsor or circumstances to advance your career or move it in the direction you want, that that’s really your responsibility, I think then the path forward becomes quite clear.

Right Work vs. Wrong Work

Benji Block: You lay out right work and wrong work. How do you see both of those helping better define our path moving forward?

Sara Holtz: Great. I coined this phrase, “right work” — although I think other people have also used it — and the concept of right work is that each of us has some value proposition that we can contribute to the world and that thing is, it’s not a job.

Basically, it’s a role that draws on your personal strengths, that leverages your personal strengths and it’s something that you do oftentimes better than others. It comes out of a variety of literature about how we discover our strengths, whether it’s Strengths Finders or Colby or Myers-Briggs or whatever. 

When you start to realize, you have some unique strengths, which are different than your co-workers, and when you leverage those strengths, that’s what I call your right work. So, right work is work that, when you do it, you produce great results. It’s relatively easy for you to do versus your wrong work, which is really hard to do. It is satisfying when you do it and again, it’s where you make your biggest contribution.

Your wrong work is kind of the opposite of your right work. I’ll give an example, I’m not particularly technologically savvy. My right work does not involve implementing technological change or being a visionary about how technological change, technologies might improve my workflow or things like that. That’s my wrong work. That’s the stuff I hire other people to do because, while I can figure it out, it takes me a long time. I’m not very good at it, it’s draining, and I find it very frustrating.

Whereas, for example, asking people questions is my right work and I love doing it. People praise me for the fact that the questions that I ask are really thought-provoking and help them move forward in their careers. When I do it, I’m excited, that’s my right work. It’s really a process of paying attention to when you’re in the zone or in the flow. 

There are a lot of different phrases that are used to describe it, versus when you are struggling or frustrated and what this, the concept of right work versus wrong work is that, when you do your right work, you get better results, you like your job more, you are having a bigger impact on other people and so it really is a worthwhile pursuit to figure out exactly what your right work is versus what your wrong work is. 

That actually turns out to be a much more difficult thing than you might imagine because, for a lot of people, they’re good at some things but they’re not really their right work. In other words, they’re capable of doing it but it doesn’t produce that kind of spark that allows them to really have an impact to really enjoy what they’re doing to really make a difference. 

Benji Block: Sara, when did you notice that asking questions was your right work? 

Sara Holtz: I wish I could say that it was earlier than it was. First of all, I mean I think for many people and myself included, we don’t even really understand this concept of right work — and again, there is a lot of confusion between what you are capable of doing and what your right work is, and I’ll give a very concrete example of that. 

When I was the general council of a company, I had staff and I managed them. I did a reasonable job. We’d have to ask other people how they felt, but we produced good results. Managing people is not my right work. I never liked it, there was nothing that was intuitively obvious to me about how to do it, so I think I probably made a lot of mistakes and I found it very draining. Anytime I had conflict with people or whatever, that was really difficult for me to do and so I started noticing — I have to say that this was well into my career, so I hope for my readers and our listeners here today that they start paying attention to this issue of right versus wrong work much earlier in their career than I did. But I started noticing that people would say to me like — We would be in a meeting and we would try to be problem-solving and I would ask a question and they would go like, “Wow, that is such a great question.” 

Or, this is very concrete, but I would often ask people, we would be in some kind of a planning meeting or making some decision about how we were going to move forward with something and I would say, “So what’s our objective here?” and the room would go quiet because basically people were coming from a very tactical point of view like, were we going to use email or were we going to use social media to push this message, right? 

They weren’t really asking the question about like, “What are we trying to do here? Are we trying to increase sales? Are we trying to develop our credibility? Are we trying to attract new people to come to work for our company?” and all of those are different channels obviously and they depend on what you are trying to achieve, right? If you are trying to reach a millennial audience then say probably email is not a great tool, right? 

That was how the conversation went, which is like basically, “How do we approach this? What are we approaching it for?” so that was a very kind of that was — 

Benji Block: When you’re stuck in the what and how. 

Sara Holtz: Yeah, and so it was really after just listening to people time and time and time again say to me, “Wow, that was such a great question” that I realized — like I mean, I figured everybody did it. As long as you are curious — and I guess that’s the big assumption about people, but — assuming you are curious, asking good questions isn’t hard but apparently, that’s what I discovered. Asking good questions, like you’re doing, is not necessarily come naturally to people. 

Benji Block: Yeah, when you’re stuck in the what and the how, you need a why person and so I love that. I love hearing how you develop that because I think for many people, whether this is kind of their zone of genius or it’s something else, paying attention to what people compliment you on is a great way of figuring out what you’re actually good at and so that actually leads to where I want to go next. 

One of the steps is to ask for help and I think this is a huge one. It advances personal learning, it builds connections, but it can feel a little overwhelming to identify where to start and you give this advice. You say, “Spend time crafting asks that are appropriate to your relationships and easy for the other person to respond to.” What would be an example of a way that we can ask for help and really lean into where we ultimately want to end up and to be in that kind of zone of genius? 

Sara Holtz: Well again, you highlighted something I say in the book, which is that the asks that you make of people need to be appropriate to your relationship. The other thing that I would urge people to do is to make asks which are very specific, not like “what kind of career advice would you give me?” but, “I am having difficulty working with my boss. They are micromanaging me. Do you have one piece of advice about how to deal with a manager who micromanages you?” 

Benji Block: That’s a good question. 

Sara Holtz: Yeah, that is both a good question and a good ask because it’s very specific. If you say to me, “What kind of career advice do you have for me?” Well, I’ve just written a book that took me two years and 150 interviews to write. Other than telling you these nine themes, which, in and of themselves are not much advice, they are just categories, I’m going to really have trouble racking my brain. 

First of all, I don’t know what situation you’re in. I don’t know what the challenges are that you’re facing, I don’t know what your goal is so I can’t actually give you very valuable advice. I’m going to be like, “Hey, what career advice do you have for me?” I would say, “Why don’t you read my book, and if you have a question afterwards, I would be delighted to answer that”, right? 

Whereas if you say, “I’m having trouble working with a boss who micromanages me” I might then say, “Okay. Well, have you thought about doing X?” or “Tell me a little bit more about your manager so I could understand why they might be micromanaging you” or, “Tell me a little bit more about places where they are micromanaging you and let’s talk about how you might approach changing that dynamic.” 

That’s very different and you know I would be happy to brainstorm with you about that. That’s very different than asking me, “Can you give me some career advice?” 

Benji Block: The more specific, the better when it comes to asking. 

Sara Holtz: Absolutely. So in this case, we are talking about asking for advice. Sometimes the help you’re asking for is actually a very big deal. You know, “Will you introduce me to so-and-so because I’d be interested in a job working at their company?” or, “Would you invite the three of us to go out to lunch?” That’s a pretty big ask, right? That’s not an appropriate ask for somebody who’s just read my book. 

That’s a completely appropriate ask for the daughter of a very close friend of mine, right? When I talk about your ask needs to be appropriate to your relationship, I get asked all the time for advice of help that is completely inappropriate for relationships. You know, one time recently somebody very junior in her career asked me if I could introduce her to any vice-presidents I knew at companies because that’s who her target market was. 

I was just like, “I don’t know anything about you. Why would I use my social capital in a situation where I don’t have a clue who you are” or you know, “You’re asking me to basically be a referral or reference for you and I’ve never even seen you work?” 

Benji Block: In that situation, if she had approached you with a better question, what do you wish her question would have been? 

Sara Holtz: Something like, “What do you think I should do over the next six months so that I’m in a position to meet, you know, a vice-president at Google?” 

Benji Block: That’s good and that goes back to the specific because she could still ask you a question but it’s not asking you to do something that would be way beyond what you would be willing to do at that level of relationship. 

Sara Holtz: Exactly. I am almost willing to give advice to anybody, assuming that it is well-framed, but you know, asking me to actually put my reputation on the line by introducing somebody and suggesting that they would be somebody good for them to hire, I’d have to know a lot more about that person. We’d have to have a much deeper relationship. 

You Are The Architect of Your Career

Benji Block: Well, we’re going to start to wrap up here but there is no doubt that and you hit on this towards the end of your book that there are areas where gender bias is still needing to be addressed and — 

Sara Holtz: Rampant is the word I use. 

Benji Block: Yes, and I think that is the correct word usage. For women experiencing that today, I thought we maybe just give you the floor here to give some advice and then we’ll start to conclude. 

Sara Holtz: Well, you know that’s kind of one of those broader questions than is easy to answer. Again, I think it depends on the situation people are in. It depends on what they’re trying to achieve, it depends on the people that they’re interacting with. Sometimes confrontation is the appropriate way to deal with that, like to say, “Would you have said that to a male candidate for a job?” or, “Would you have said that in evaluating a male’s performance?” 

Again, sometimes the only thing you can do in this situation is to make a mental note of it and realize, “This is something I am going to have to work around.” This goes to owning your own career. I don’t have any broad-brush advice about how to deal with gender bias in the workplace. I think you have to really look at the situation and understand what the dynamic is. 

The other thing I would say is that this is a mindset thing. Again, going back to the issue we talked about, about owning your career, which is to say that you are entitled to work in a workplace that is gender discrimination-free and so it’s not something you just like have to put up with. Maybe the answer is you go to HR, maybe the answer is you talk to other people about what their experience is. 

Maybe it’s you sit down with your boss and say, “You probably didn’t intend this to be the way I experienced it, but you should know this is the way I experienced it,” right? Maybe you kind of get a posse together to address the issue. I guess I don’t have any very useful advice about anybody’s specific situation, but I do think the mindset that this is not something you have to put up with is an important one to enter the workplace with. 

There are ample conversations in society today about how this is not a good thing and so I think a lot of times it’s unintentional or unconscious that some of the bias takes place. Not always, sometimes it’s very mean-spirited and it’s designed to make you feel uncomfortable and like you don’t belong. I’ll give an example of this. I had a client once and she said — she was the boss, right? 

They had a Monday morning all-hands meeting. The meeting would always begin with about 15 minutes of conversation about sports, and you know, she was sort of taken aback by this. Now, there is plenty of women who are sports addicts but she wasn’t one of them and so she one day finally said:

“Hey guys, have you ever noticed that when you have this 15-minute conversation before our weekly meeting, which is really designed for all of us to get to know each other better, to have some common experiences and to build our relationships, you guys are talking about sports and I’m not saying anything? That’s because I’m not following sports and I want to put that out to you guys because I know you’re not doing it to be exclusionary or to make me feel bad but that actually is the impact of what you’re doing. So can we talk –”

Benji Block: Having it pointed out is important. 

Sara Holtz: Yeah, “So, can we talk about what people did on their weekend or what everybody’s binge-watching these days? Can we kind of just changed the context? I love the fact that we’re having a conversation where people are getting to know each other and having a positive impact and you know, starting the week off on a good note but I think we need a different topic.” 

Benji Block: That’s good. Well, as we start to wrap up here, when someone finishes this book, a woman finishes reading this book, what is it that you hope that they feel more than anything? What do you hope they feel when they finish this book? 

Sara Holtz: Great question, empowered. 

Benji Block: Good.

Sara Holtz: That they are the architects of their career. What I am really trying to point out to them is ways in which they can build the career that they want by asking for feedback, asking for help, learning to say no to things that get in the way of their pursuing what I call yeses, all of those kinds of things. My goal for the book is really to give women some tools so that they can be the architects of their careers. 

Benji Block: Sara, for those that they’re going to check out the book but where else can people follow you and reach out? 

Sara Holtz: Well, I post pretty regularly on LinkedIn under Advice to My Younger Me and I have a website, which is tomyyounger.me where all of the previous episodes my podcast are and also lots of articles that I’ve written. When you go to the website, there is an opportunity to sign up for my newsletter as well and that’s a monthly newsletter with some very specific and practical tips about how to pursue your career. 

Benji Block: Well, Sara, it’s been an honor to discuss the book. Great work and thank you for taking time to speak with us on Author Hour today. I know Advice to My Younger Me: Career Lessons From a Hundred Successful Women, is going to be a great resource for so many. 

Sara Holtz: Well, thank you so much, and thank you for such great questions. I really appreciate it. 

Benji Block: Absolutely, thanks for being on the show.

Sara Holtz: Take care.