Please Meet “Future You”

Welcome to the Future of Work podcast with Berkeley Extension and EDGE in Tech at the University of California, focused on expanding diversity and gender equity in tech. EDGE in Tech is part of the Innovation Hub at CITRIS, the Center for IT Research in the Interest of Society, and the Banatao Institute. UC Berkeley Extension is the continuing education arm of the University of California at Berkeley.

This month, if you’re looking to reinvent your career, reboot your confidence or rethink what’s possible, we’re going to give you some time, space and strategies to imagine your next move. The past is not a fortune teller. It doesn’t dictate your future. The past is, however, an excellent teacher that offers us useful lessons but not limits.

So how do we tackle finding a future career path with a minimum of stress and self-doubt? To talk about this, we’re delighted to welcome Andrea Liebross, a results-focused business coach and life balance architect. She works with unapologetically ambitious female business owners who are ready to grow strategically through big thinking.

Through results-focused coaching, systems and intelligent decision making, Andrea helps turn ideas into action and businesses into legacies while still ensuring life integration remains at the core. Andrea is also the author and podcast host of She Thinks big. Welcome, Andrea.

Andrea Liebross: Thanks for having me.

Jill Finlayson: Let’s start with the past before we jump into the future. Where did your career start out? And how did you get where you are today? Was this a gradual evolution, a big pivot, a planned journey?

Andrea Liebross: It definitely wasn’t a planned journey. I’ll say that. I think it was a gradual evolution.

I graduated from college. I graduated from Dartmouth back in the ’90s. I moved to New York City. I worked in a big ad agency. Those were the days of, anyone who’s old like me listening, Ally McBeal. So it was kind of an Ally McBeal ad agency situation. But then I got engaged, and my husband, my future husband, had to move to Houston, Texas, for his residency. He’s a physician. So that was a turning point. So we got married, moved to Houston, and I said, I don’t want to go back into the rat race, what felt a little bit of a rat race in advertising.

And I pivoted and got a master’s in communication disorders while we were in Houston and lived there for a while, moved to Indianapolis after his residency, where he started his real world job. And I then put my master’s degree to work and worked in a hospital environment, actually, for a few years. But then I had kids, and that job was not going to work in our family dynamic. He didn’t really have much control over his schedule, and I wasn’t going to be able to have much control over mine. So I took one for the team, we’ll call it, and I moved into working part time. And at that point I really decided I didn’t love what I was doing again.
So I started working for more of a corporate entity in a role where I was recruiting and hiring and training. I fell into this role, as a lot of jobs, as we know happen, that you fall into it. And I stayed with that company for 10 years. And when I left, I really assessed, why did I stay there for so long? It seemed like so long, those 10 years.

And I hired my first coach at that point, had never worked with a coach before. And I still have a vision in my brain of where I was sitting when she said to me, what you really loved about that role was coaching. And I had never thought of it like that. I was just, in the corporate eyes, training people on how to grow new businesses.

And it really wasn’t training. I don’t think you can really train someone to be honest, if we look up the definition of the word. The part I love the most was now I would call coaching them through the messy middle, which really means when you have decided, made a decision to embark on a new endeavor. And this doesn’t have to be with growing a business. This can be with anything.
This can be your educational career too. You embark on it, and you have excitement going into it. You start to see some success, or things are paying off. And then it starts to feel really messy.

How do I get to that next level? Or how do I make this feel easier? It doesn’t feel easy anymore. It feels really hard and complicated.

You might have some guilt infusing the situation at that point because you’re using a lot of resources to keep things going, time, money, energy, people. And I really loved helping the mostly women I was working with at that point move through that and get to that next level. So when I really dug deep and figured out that was the part I liked, I thought, all right. Maybe I should just be doing this not under that corporate umbrella and doing this work on my own on my own terms.

Thus was born a coaching business at that point, which is seven or eight years ago now. And I am still working mostly with female entrepreneurs and helping them grow their business. But I also have now, at this point, written a book and have five years worth of podcast episodes out there on my own too. And I speak to audiences around the country, and so that’s really the long version, Jill, of the gradual evolution with a few pivots. But none of it was planned until it was planned.

Jill Finlayson: I heard a couple of things in just your recap that I’d love to know, how did you figure it out? What made you aware that you were not in the right job?

Andrea Liebross: I think it’s actually an interesting mix or merge of a couple different things. Some of them I just didn’t like how it aligned with what was happening in my family. So I think we always have to remember that part. I didn’t like the hours I was working at one point in relation to when my kids were awake. So I didn’t like that part.

Other points I didn’t like, the fact in that corporate role where I would come up with what I thought were great ideas, and then they had to get passed — they would be identified actually as great ideas. But then they had to go through the powers that be, and they never would come to fruition. And that was really frustrating to me at one point. So I didn’t like the dynamic, we’ll call it, or the hierarchy of things.

In another job I had at one point, I didn’t like the lack of control I had over my day to day. So it’s interesting because a lot of us say, oh, we want things to always be varied and different. We do, but our brain does like some consistency as well. So one of those jobs I had, it was just too much chaos all at one time.

So I think why I switched jobs or career paths or took a different trajectory was never one thing alone. It was always a combination of things. And I think that’s still true today.

The people that I’m working with today, as I look at my own kids who are in their early 20s, it’s never just one thing, I don’t think. I think it’s always just a combination.

Jill Finlayson: Why do you think the past is not the best indicator of the future? Oftentimes we think about you get your first job. Then you get more responsibility. And then you get more responsibility, and you move up. But it’s based on your past performance. Is it a good model?

Andrea Liebross: I think moving up within an organization does — in like their eyes, them versus you, they do have to go on something. So I think past performance is helpful if you’re the employer and thinking about, does this employee need to be elevated?

But if you’re the employee, you are in charge of your own destiny. And yes, you can learn things from your past. But like you said, it doesn’t have to tell the fortune of where you want to be. So I think what’s interesting, if you think about pivot versus plan journey, a lot of times the past tells us what we don’t like.

But it doesn’t tell us what we do want or like. And that has to come somewhat from your imagination or your giving yourself space to think about things or your dreaming abilities. And that is all future based. So I like to say you’ve got to take some direction from that future you, and you’ve got to think about what would he or she like doing, or what do you want your family dynamic to look like? And how is your work going to integrate into that? So you can learn from the past, but it’s not always going to tell you what the future holds.

Jill Finlayson: Who is the future?

Andrea Liebross: You’ve got to think about future you with a big smile on his or her face. They are liking, loving what they’re doing. Are there difficult challenges? Yes. It’s not smiles all the time.

But they are feeling successful. They are feeling probably purposeful. They are feeling like things are flowing in their lives. They are feeling energized by what’s happening.

And so if that’s the case — and you have to really dig into the feeling aspect of it — then what are they doing? What is that future you doing? And if we think about feeling like things are flowing, energized, smiling, balanced, potentially, what are they doing in order to create that? What role or job or profession or business are they in?

And if you give yourself enough space to think about that, then you can go to future you and say, OK, future you, what should I do today? So I like to say future you is really a person. It’s you three or five years from now. So picture all of this as an actual human. And it’s like you’re meeting future you. You need to go become friends with that future you.

So future you is, out of that curiosity type of thinking, urging you to try on different ideas, almost like you’re trying on — you’re in a dressing room at a department store, if we actually go into stores these days. And you’re trying on different outfits. You’re trying on different clothing.

Or you’re trying different sports. What are you trying on? So future you is very much ambitious. Future you is someone who’s willing to explore and to really try on the options.

You’ve got to be open to options. And I think when you’re in that dressing room, if you’ve ever had anyone help you in a dressing room and they say, hey, I know you kind of passed over this on the rack, but I actually think you should try this on, you should try — I’ve seen it on other people, and people seem to really like it. Will you give it a try?

And that’s the same in our professional life. I’ve seen this work for people who seem similar to you. Have you ever thought about this? Give it a try. Try it on.

Or I know you really don’t love red. But there are 52 shades of red. So the pinks might actually work out better for you. Pink’s a shade of red. Would you try this on? So future you is almost like that sales person that’s outside the dressing room that’s handing you things over the door.

Jill Finlayson: And it sounds like future you is not alone either. There are other people who can help provide ideas.

Andrea Liebross: Yes, yes. So I think you’ve got to get yourself in a position where you are fully supported. You are fully supported. You are not just relying on your friends and family to help guide you.

They’re almost more commiserators in a way. Or they can validate what you’re thinking. But are they pushing you? Are they challenging you at all? Are they throwing over the green things over the edge of the dressing room to you? Or are they being like, yeah, I know. You never wear green. So that’s OK.

Your friends and family, their job is to love you and support you in a way that feels good to you. But who else is supporting you in a way that might be a little more honest or a little more exploratory or create a little bit more curiosity or push you into a little bit more of a risky risk-reward type of situation?

Everybody needs those kinds of people in their lives too. And they can look like mentors. They can look like coaches. They can look like colleagues. It could be your best friend, if that’s the kind of relationship you have. But I would encourage everybody to get out there and see, who do you have in your support network that can help future you move this thing along?

Jill Finlayson: Yeah, I’ve been very fortunate to have a number of bosses who have both given me enough rope to go do things but have also given, what you’re suggesting, a nudge or a push to take on something that might seem a little audacious.

Andrea Liebross: Yes, yes, which could be big thinking in a way, which is another thing that I really am a proponent of, thinking big.

Jill Finlayson: What is thinking big?

Andrea Liebross: Thinking big is the kind of thinking that comes from future you, first of all. But when we are talking about our future or making decisions as how to move forward, big thinking is really a tool that you can have in your toolbox. And I use an acronym TRUST, T-R-U-S-T, to describe what big thinking is all about. And TRUST has five letters in it, and I say that there’s five keys to thinking big.

Jill Finlayson: All right, let’s break it down. What is the first T in TRUST?

Andrea Liebross: So the first T in TRUST stands for thought options. And you have thoughts about every single thing, every word someone says out of their mouth, every fact that’s out there. So if you are saying, OK, it’s sunny and 70 degrees today, it’s a fact.

We’re in Berkeley. And I am not in Berkeley, but let’s pretend I’m there with you. And it’s sunny and 70. Some people may have a thought or you might have a thought at 8:00 AM, ugh, why is today, this Monday, 70 and sunny. Yesterday it was raining and 50. So your thought is, I wish it wasn’t 70 and sunny today. I wish it was yesterday. That could be a thought.

You also could have a thought at 8:02 because your brain likes to switch quickly, oh my gosh, this is going to be great. The drive to work is going to be so much easier. So happy it’s 70 and sunny.

Or you could, I can’t wait till 4:00. That’s what I’m going to be able to get outside and take advantage of the day. So there are facts out there, and we get to choose which thought we want to have.

Then the R in TRUST stands for real problems. So all big thinkers know that the real problem is really just the fact that you don’t want to feel something negative. There is no real problem. The only problem is you don’t want to experience negative thinking.

The U in TRUST stands for embracing the unknown. So we don’t even know what’s going to happen this afternoon. We don’t know what’s going to happen tomorrow. Our brain really wants to know though. It doesn’t like unknown or uncertainty.

But big thinkers have to probably take some risks. Future you, future you is probably a risk taker. So all big thinkers out there, they have to embrace the unknown or uncertainty.

Then S in TRUST, S stands for secure support, which actually we kind of hit on previously. Everybody out there that is a big thinker, I don’t know any of them that are doing it alone. They all have some type of support system that are really going to serve — as I like to say, they’re going to be able to read the label. So you are stuck in the jar. You’re stuck in your own peanut butter jar. And it’s so sticky in there that sometimes it’s really hard to see what’s happening, and you need someone to point that out to you and for you. So that’s what the S stands for in trust.

And then the last T in trust stands for taking massive action, taking massive action, not passive action. Passive action is reading a book. It’s listening to a podcast. Now, clearly I like both things.

It’s not like I don’t like reading or listening to podcasts, but that’s just us absorbing information. Are you doing anything with it? When I do my own podcast, I always have a homework section, and I say, OK, thank you for listening through the whole thing. You’re still here with me. Now I want to give you some homework where you can take some massive action. So for the last T in TRUST stands for take real massive action.

Jill Finlayson: I like massive, not passive. [LAUGHS]

Andrea Liebross: Yes.

Jill Finlayson: That’s great. When I think about this, I used to work at eBay, and they had a phrase called BHAG, big, hairy, audacious goal. And the idea was you wanted to go for exponential growth, not incremental growth, and you wanted to have a big goal because, if you fell short, you still went further than you thought. But for a lot of people, they might ask, why do I have to think big? Why I just think next?

Andrea Liebross: Hmm, OK, so this is a great question. And I think what happens here is, if we think next, what is the next best step? It’s a great question.

But is it pushing you farther faster? So I like to think about, what if we dismiss next step and we go right to leap? What would a leap look like?

And leaps are actually way more powerful. And leaps are sometimes made up of little next steps. But if you can get your brain to the leap place, you are going to see more progress.

So I was on a coaching call the other day, and we were talking about this, same thing here, the next step versus the leap or having that big, hairy, audacious goal versus just a next step. And my client said to me, I feel like I’m successful. I’ve seen success. It’s not just a feeling.

But I want tremendous success. She kept going back to that word “tremendous.” And we actually googled it, and we looked. We got all geeky, and we figured, what did Webster’s dictionary say about “tremendous?”

And it really has this sense of largeness to it. But nowhere, nowhere in the definition did they mention the word “scary” or “fear.” So I think sometimes that’s what prevents us from going towards those big things or taking that leap. But it doesn’t have to be that way. So I would say go for the leap.

Jill Finlayson: The association I have with leap is kind of interesting. When you think about social entrepreneurship or developing economies, one of the things we discuss is they don’t have to repeat the mistakes that other countries have made. They can leapfrog. They can go right to a better solution rather than going through mistakes and evolution that other countries went through. Do you think there’s a similar parallel for people?

Andrea Liebross: 100%. So this could go back to the past as a teacher. What do we remember most? We don’t remember those little next steps. We remember the big, big changes.

Or when I was recounting my last 30 years, I gave you some highlights, and those were really the leaps. They weren’t the small steps. So that is a good analogy.

Jill Finlayson: That actually reminds me of when people write their resume, that is the summary of their successes. It doesn’t necessarily talk about their failures. What role do failures play in this growth and career planning?

Andrea Liebross: Well, I think, if you’ve ever gone through the exercise of doing a life plan — have you ever done that? It’s like a — OK. So it starts to look like a graph of ebbs and flows or peaks and valleys. And you plot out, hey, these were my successes, and they’re the peaks. But then these were the lows.

And in the instructions to do this life plan, it prompt you to look at the lows. And you realize that sometimes there’s just as many lows as there are peaks or such as many valleys as there are peaks. And I think what that does is it helps us assess — looking at those valleys or lows helps us assess, why was that a low? Or why does our brain associate it as a low?

And it tells you a little bit about what you don’t want, but it doesn’t necessarily tell you what you do want. And I think that’s where you have to honestly rely on yourself a little more and not the facts. That’s where you have to — we’ve all heard the expression like, you’ve got to lift yourself up out of this. Or I just, I just — I’m putting just in air quotes — I just have to get over it and move on. There’s another expression. But is it telling us what we have to move on to? Not really.

So the lows or the valleys tell us what we don’t want, what we don’t like, what we don’t want to feel. But they don’t necessarily tell us how to get out of it. And that’s where you have to rely on that future you to almost pull you out of the valley or pull you out of the low.

Jill Finlayson: I think there’s a couple observations which people forget or overlook, which is that it’s not a smooth ride here. You don’t just have a career path that goes uphill. It’s these dips and valleys all the way along the way.

Andrea Liebross: Yep, yep. And I think you have to think about what might pull you out of the valley. You have to think about, what might make this a home run for me? What would help me jump out of the valley? What would feel amazing?

And sometimes that’s hard to do. I think it’s easier to do when we’re looking at someone else and thinking, what would make this a home run for them? What do we think they want? But when we’re doing it for ourselves, it’s a lot harder.

Jill Finlayson: In this economy, even ambitious folks may feel anxious or stuck or almost feel like they have to stay where they are because it’s a little bit safe. How do you help people think about risks and rewards and embark on this journey?

Andrea Liebross: Well, I like to think about using a thought bridge. So how do I get from where I am now to where I want to go? How do I embark? Thought bridges link your past to your future.

And I think of literally a bridge, a wooden bridge with planks, and you’re on one side. It’s called the land of impossible. And then on the other side, where you want to go, is the land of inevitable. And as you go over, you get to a peak in the bridge because the bridge is a little circular type of rainbowy bridge.

And at the top is what is really possible. But each step or each plank in the bridge represents the next best step. And to get over, you’ve got to train your brain to figure out how to keep moving forward.

So what do I need to do? I need to get out there and ask some questions. That’s maybe step 1. OK, I ask the questions. Now I’m going to take the info, come back to home base, synthesize, decide what my next best step is. OK, now I took the next best step. I didn’t ask questions. I actually put my resume out there, for example.

OK, now the resume is out there. Now I have to follow up. Each of these wooden planks represents a next best step. You get to a place at the peak where you feel like, OK, I think I’ve got some traction. I think I’m actually going to get over the bridge.

And our brain, though, wants to leap from one side of the river to the other. And I think that’s a good thing to keep in mind. However, you do have to figure out what each next step is and to think about, what do I need to do to actually shine as I move forward?

What would make it a home run for the people that I’m going to get in front of? What do they really need? What do they really want? And how do I show up on that next plank of the bridge in a way that’s going to do that for them?

Jill Finlayson: I think a lot of people do feel like they’re living in the land of impossible, but it’s really hard. You mentioned submitting a resume, but that’s the tip of the iceberg, right?

Andrea Liebross: It is. It is. That’s the easy part.

Jill Finlayson: And people are submitting 200 resumes and not hearing back or getting rejection. So how do you help people with the mindset? What do you mean by mindset? And what kind of shifts are you asking people to make?

Andrea Liebross: I just experienced this with my own kids actually. So they’re entering this job market, and that 200 resume thing is a real thing. That’s no exaggeration.

And unfortunately, there’s no follow up even sometimes. You don’t know because it goes into oblivion, and you’re just waiting and waiting and waiting. What do I even wake up and do today?

So what I think you have to assess is your resources here that you have in moving into that next phase of life, that next job, that next business, that next whatever. You’ve got time, money, people, people around you, and you have energy. Those are your four most valuable resources.

And those are the things that are going to help you move past that barrier or get into that next place. And they can be barriers in and of themselves, or they can be used as tools. So you might say, I don’t know if applying for this job is going to give me as much money as I have right now. The money might not be as good.

Should I go for it? Well, are you giving equal airtime to the money might be better or time? I don’t know if I can get flexibility, the same flexibility that I have now, elsewhere. Well, what if you got even more flexibility?

So here’s this equal airtime type of thing. Here’s where future you is pulling you over the bridge. People, am I going to the people I’m working with or not? My people right now, they’re pretty good. I don’t know if I could create a better situation.

What if they were even better? What if they were even better supporters of you? What if they helped catapult you into that even next opportunity?

The last thing, and the most important thing I think, how to move past the barrier, how to get beyond the 200 resume abyss is tapping into your own energy or your own brain power. That is ultimately your most valuable resource in all of this because you can use your brainpower to create more time or more money or get yourself with the right people.

Are you spending your energy or your brainpower on the right things? Are you stuck in the here and now? Or are you working toward the future? And I’ll give you an example.

My son actually just went through a job search, but he did sign a contract last week. So thank you, Lord, for that. But he had put his resume out there, and he was working with headhunters too. And things seem to be either going into the resume abyss. Or he was getting through to the final round of things, but nothing was clicking.

And we had this whole discussion, and he just felt like he was up to — there was a barrier. So there was one company he was really interested in, and he lives in Boston. And this organization was in Nashville, Tennessee. And I said, what if you asked the headhunter if any of the top dogs ever come to Boston?

Because they did have clients in Boston. He figured that out. And could you meet in person with someone from the organization? Could you meet for coffee or drink or whatever?

And to him, that seemed like, mom, no one does that. Everything’s on Zoom until you get to the final round. That’s not happening. It’s not happening. Of course, what do I know too? I’m just his mom.

So he did. I’m sure you can figure out what the end of the story is here. He did do that. And sure enough, a guy was coming to Boston the next week, and he met him. It was like 25 minutes, he said.

He met them in the ground floor of his building in downtown Boston. They, I don’t know, must have had a great conversation because the next thing he knew, he was invited to go to Nashville. And that is the job he actually landed.

If we go back and we look at all the jobs he applied to, he hadn’t met anyone in person at any of these organizations until that very final round. So my point here is he had to use his brainpower — and he borrowed a little of mine — to create more opportunities. And I think that’s what you’ve got to really go back to is your own energy and your own brain power, aligning it with that future you.

Jill Finlayson: So I’ve both been this person and met people who have been in career positions which have, I would say, beat them down, have affected their self-esteem. How do you help those people get on the first plank when they’re just feeling a lot of self-doubt? How do you help those people?

Andrea Liebross: Yeah, this is hard stuff. This is hard stuff. But I think you can go back to, what do you have in your court?
So you’ve been beaten down. You don’t love what you do. You feel like there is no hope.

But what do you have? You have skills. You have solved problems. You have people around you.

You have opportunity. You can learn things. You can tap into your brain power. You can figure out what that next job might be looking for and learn how to do that. There’s the thought option type of thinking.

Jill Finlayson: The thought options, you have to believe that there is something out there for you. So it seems like the first leap you have to make.

Andrea Liebross: Yeah, so the first leap is really about belief. And when I work with my clients, a lot of times they’ll come to me, and they’ll just say, what do I need to do? So they want their action plan, all right, which we all want an action plan.
And then they’ll say, and I’m on this timeline. I really want this all to happen before January 1. OK, got it. We can create an action plan. We can create a time plan, our timeline.

But do you have a belief plan? And then they look at me like, what are you talking about? This is like, way too woo. And it’s not woo, OK. It’s not.

What do you need to believe in order to land that next position? You’ve got to believe that you have something to offer. You’ve got to believe that there is some person, some organizations, some firms, something that wants to work with you.
You’ve got to believe that an old dog can learn new tricks. You’ve got to believe that, yeah, there can be something that’s way more flexible than I have right now, even if you think you’ve got great flexibility. So there’s a lot of this you’ve got to believe in the possibilities and the opportunities.

So I like to say, yes, you need an action plan. Yes, you need a time plan. But you also need a belief plan. And that’s what’s really going to start the ball rolling. That’s what’s going to even get you to the bridge.

Jill Finlayson: So if you have a belief plan, going to the R in TRUST, how do you know if you have an actual real problem or it is that negative thinking? What is an activity to help you figure out, is this a problem? Do I have a gap? Or is this something that I’m just holding myself back and I’m self-limiting?

Andrea Liebross: I think you have to look at it through a different lens. So I like to say change your glasses out. And would someone else that is not engrossed in the situation consider this a problem? Let’s say you’ve submitted the 200 resumes, and you’re telling everybody in the world, I’m just not getting any bites. This is horrible. I have a problem. There must be something wrong with me. Maybe there’s something wrong with my resume. Maybe I need to tweak something.

Yeah, maybe you do need to tweak some. Maybe you’re right. But what would someone say to you, is that a problem? No, they’d probably say, yeah, but you might get a new job when you submit resume 201.

So you have to go back to thought options. Would someone else consider this a huge problem? Or would they say, well, it’s not really a problem, it’s just that you don’t like how this feels right now? Because it doesn’t feel good to not get any response after 200 resumes. So 99.999% of the time there really isn’t an unsolvable problem. The real problem is just that you don’t want to feel a certain way.

Jill Finlayson: You mentioned earlier Ally McBeal. I’m going to date myself as well here and talk about the X-Files with FBI agents Fox Mulder and Dana Scully, and they come to mind because they’re investigating unexplained cases. And you were saying that you have to embrace the unknown.

Why are people uncomfortable? We just talked about having to feel uncomfortable. Why do people feel uncomfortable with the unknown?

Andrea Liebross: So if we put our neuroscience hat on, there’s something called the motivational triad. And as humans, we’re motivated by three things. We want things to feel comfortable. We want to be safe. And we want things to be efficient.

And when you’re talking about pivoting or changing trajectories or starting a new endeavor, there is nothing comfortable, efficient, or safe about any of those. So if you go back to like caveman era, the caveman didn’t want to come out of the cave because he or she were scared of what was outside of the cave. So let’s just stay in this comfy cave.

Let’s hibernate. Let’s stay in. Even if you don’t like where you’re at, it’s safe. It’s human nature for us to not want to do something new, do something that might be a little bit hard.

It’s definitely not efficient. There’s no efficient thing about 200 resumes. There’s no comfortable thing about meeting someone in an interview situation.

So it’s almost like, no wonder we want to stay in the known or in the certainty. Of course we do. That’s motivational triad.

But we can’t create change unless we do embrace that unknown or that uncertainty. And I think what captured our attention with Fox Mulder and Dana Scully in investigating these unexplained cases is that there’s an excitement.

Sometimes you say, how do you feel? Oh, I’m excited, but I’m nervous. Usually excited and nervous or anxious and excited, they’re words that kind of sometimes go together. And that is because we’re excited about what might be possible. There’s our curiosity factor. But we’re nervous because we know we’re going into a territory where it’s going to be hard and uncomfortable and efficient.

Jill Finlayson: So reframing the scary into exciting.

Andrea Liebross: Yeah, and both scary and exciting, if you think about it, are fleeting. So go back to that life plan with the peaks and valleys.

It is a peak. It is a split second. And it’s a valley. It’s a split second, a roller coaster ride. They’re quick.

So there’s excitement and fear, excitement and fear, excitement and fear. So I think in life what we’re always searching for is that happy medium, the middle, the neutral, where we don’t have to feel either excited or anxious. We can just be at peace with things. We can be content with what’s happening.

And whether that’s us solving an unexplained case or looking for a new career or job or going back to school, whatever that is, we just want to get into it and start to figure out what our day to day is going to look like, and you have to know that that is at the other side of the rainbow. You’re going to get into it. You’re going to reach a place of neutral eventually.

Jill Finlayson: And going to the S in TRUST, securing support, what is the tactical plan for securing support? Because, as you alluded to, we’re much harsher on ourselves than our friends are.

They ask us for advice. We’d be like, yeah, you can do it. Yay. But if we ask ourselves, we’re like, no, I can’t. So how do you secure support? Do you make a list of people to talk to?

Andrea Liebross: I operationalize it by saying, who do you want on your personal board of directors? And that’s a really good analogy and operational standard that you could go through.

So if you think about organizations, they comprise a board of directors, that it’s handpicked. They want someone on that board of directors who has finance experience, legal experience, depending on what the field is maybe some medical experience, running teams, whatever the organization is. But they handpick who’s on the board of directors.

So who do you need on your board of directors? Now, one person you might need on your board of directors is an ally or a friend who’s going to say, go for it, or that’s OK you didn’t get it. Better luck next time.

Yeah, you do need that ally. But you also need someone strategic that might say, yeah, the reason you probably didn’t get that is because you didn’t highlight your ability to do x, y, and z. They’re going to tell you the truth.

Or you might need someone on there that says you need to think about people skills. And are you highlighting all of the things that you’ve done managing others? So you’ve got to get really strategic on who is on your board of directors and try to fill the seats.

I look for someone who is asking you questions that’s going to lead you to the massive action or the next step or the leap. So that person needs to have skill in question asking actually. They are not just tellers. They’re not necessarily consultants.

They are more filling a coach type of role, going to motivate. They have to be really good question askers. They have to help you see the possibilities. And they have to be there with you through the thick and the thin, regardless of the outcome.

If you don’t have someone with you that’s going to stick with you regardless of the outcome, you need that person that’s going to show up week after week. Questions, showing you possibilities, not motivating you — you have to motivate yourself in the true sense — but who’s going to walk alongside you or who’s going to be a guide and who’s going to call you out too when you don’t make a good play.

Jill Finlayson: This may be a little stereotypical, but if women have been culturized to have friends and people that they can talk to about these things, how do you help the men you’re coaching find that support network?

Andrea Liebross: That’s a great question. It does seem a little bit harder in a sense. I think what’s interesting is the women usually don’t have trouble finding the commiserators and the allies. They have a harder time finding the strategic players in a sense.

Men, on the other hand, sometimes have a hard time finding the allies or the commiserators because that to them might be a sign of weakness. This is all just norms we’re talking about. There’s always exceptions. But I think honesty is really the key denominator here. So a woman has to be honest in saying, I don’t really understand anything about business finances. I probably should, and I’m embarrassed to say I don’t. So I need to get that finance person on my board of directors.

A male might say, I got to be honest. I could have all the lawyers, finance people, operations people galore, but I need to find someone that I can just really let it all out and be honest in that way. And I think those friendships are usually with men. I always say, look for the commonalities.

Who do you have something in common with? And ask. You have to ask. Are you asking them to be on the board of directors. That’s actually a great way to even put it. Hey, I’ve got some challenges happening. I’ve got some change up ahead. I need people on my personal board of directors. Would you be on it? And people are usually honored.

Jill Finlayson: So you’ve coached a lot of people. You’ve given them this advice. What barriers have people run into? And what’s the biggest stopper for them?

Andrea Liebross: The biggest stopper? OK, I would say the biggest stopper that our brain likes to come up with is time. I’d say that’s what our brain offers up the most, that time, we just don’t have enough time. We just don’t have enough time to fit everything in if we don’t have time to balance our family with our current job or occupation or business.

And we don’t have time then to insert something new, new goals, new endeavors. It just seems like we’re piling things on. So I think this is when you really have to get good at deciding what’s important, what’s urgent, what’s important but maybe not urgent, what’s urgent but not important, and then what’s neither urgent nor important. So let’s divide out what’s happening right now into four quadrants.

And you’ve got urgent, not urgent, important, not important as the labels of these axes. And when you put everything down on paper, you’re going to see that there are things there that aren’t urgent or important that you could delegate or delete or even schedule. They’re like, no for now, but not forever.

So there’s something called an Eisenhower matrix out there, and if you Google it, you’re going to find it. I think Dwight Eisenhower was the originator of all of this. But he has this matrix, and I have a version of it too, where I try to say, what do we need to plan? Plan meaning it’s still in the planning stages. You can’t really even schedule it because then the next step is schedule.

What do we need to do right now? And then what can we delegate? And if you get good at that do, delegate, delete, schedule or do, plan, schedule, delegate, however you want to label those things, you’re going to see that you do have plenty of time.

Jill Finlayson: You’ve called yourself a life-balance architect. So when you think about this idea of these multilayered problems, how are you helping people balance their life? They’ve got your current job. You’ve got the goals for what you want to have as another job.

But you might have elderly parents to take care of or children or pets. Or you got to repair the cars or get it smog checked. There’s a lot going on in everyone’s lives. How do you help them think about planning this career goal trajectory in the midst of all this messy middle noise?

Andrea Liebross: Yeah. How many of those things on that to do list align with that five year from now future you? How many of those would future you be like, yes, you definitely need to do that today? Do we really need to go to Target?

Is that the most important thing? Or do I need to send out 10 more resumes versus just picking up the phone and calling one person that might get us further faster? So you have to take a different set of glasses, look at how you’re spending your time, and honestly on a daily basis get that granular.

And are the things that you’re doing, would future be applauding you? Or would it just be like eh? And that’s how you have to decide where to put your energy.

Jill Finlayson: When you think about the idea of manifesting, like, I can see it, I can make it happen, if you don’t have that kind of vision, it’s hard to do that prioritization.

Andrea Liebross: It totally is. So one of the things I do with my clients, I call it a vision-into-action intensive, and it lays the foundation for the work we do together. And I get some pushback. People are like, I have a plan. We can skip that step.

But after I do that, I get many thanks because it’s creating space. It’s creating that strategic pause for you to really dig deeper into what you want, what you’re envisioning for your future, and then ensuring that how you’re setting yourself up, what you’re doing today, the actions, so vision into action, the actions that you’re taking really are in line with that vision because too often we just can go down rabbit holes or lots of shiny objects or things you think you definitely, definitely need to do.

Yet really do you? Does it align with where you want to go long term? And that’s why I think it’s so important to get your vision out there and then decide from there what your actions are.

Jill Finlayson: Yeah. I think sometimes we hope that things will just fall into place or fall into our lap, but typically that doesn’t happen. And so do you have some final tips on thinking big? Where do they start?

Andrea Liebross: I think a great place to start is this visioning. It’s hard to do by yourself because our brain wants to come up with all the excuses, like we talked about, of why things aren’t possible. Or I get the question, do you want something realistic? Or is this really in my wildest dreams?

And I think you have to go to in my wildest dreams. And that’s hard to do on our own for more than 10 seconds. So I would say grab a friend, grab a friend or someone on your board of directors and plan an hour. And you can do this while you’re on a walk even.

I recommend that you put it on paper. But if you’re walking with your phone, talk into your phone. There’s so much AI out there, too, that you could use. Talk into your phone, but have another human on the other end at least.

And have that person asking you, why this? Why that? What does that look like? What’s it going to feel like? And get it out. But give yourself a 60 minute block of time, even while you’re moving — sometimes while you’re moving, it comes out better — to get that vision down there on paper.

Jill Finlayson: Give me three prompts that I could go ask myself.

Andrea Liebross: What do I want to feel like in five years? And how does that differ from today? How do I want to be remembered? My funeral is tomorrow. How do I want to be remembered? That’s really important.

And then how do I want to show up on a daily basis? How do I want to show up for my family? How do I want to show up for my colleagues? How do I want to show up on the soccer field? How do I want to show up when I’m hanging out with friends on a Saturday night? How do I want to show up?

Those questions are not profession specific. They’re not business specific. They’re not career specific. But they’re going to give you an outline to figure out what that path looks like.

Jill Finlayson: They’re going to be the foundation. Give me a closing inspiration. How do we know this will work?

Andrea Liebross: You have to go back to our belief plan because how would we know it won’t work? I guess is a better question. What does not working look like? If you go back to my story, there are all those times when I was like, yeah, I decided I didn’t want to do that anymore.

Well, there was a time when I decided it was the best thing ever, right? And I said yes to it. So something doesn’t work only after it does work. You’ve got to be open to those possibilities.

You have to believe that it will work. And you have to believe that you’ll know when it’s no longer working. So I think it goes back to that belief plan.

Jill Finlayson: Well, thank you so much, Andrea. It’s been great chatting with you today.

Andrea Liebross: Thank you. Thanks for having me. It’s been a pleasure.

Jill Finlayson: And with that, I hope you enjoyed this latest in a long series of podcasts that we’ll be sending your way every month. Please share with friends and colleagues who may be interested in taking this Future of Work journey with us. And make sure to check out extension.berkeley.edu find a variety of courses and certificates to help you thrive in this new working landscape.

And to see what’s coming up next at EDGE in Tech, go ahead and visit edge.berkeley.edu. Thanks so much for listening, and I’ll be back next month to continue our Future of Work journey.