Ep. 32: Negotiating Your Next Career Move: Leverage, Timing, and Strategy with Debra Osofsky
What do you do when you land the job you worked toward for years and realize it still doesn’t work for your life?
In this episode of The Pivot Point, I sit down with Debra Osofsky, a deeply experienced negotiator, attorney, and negotiation trainer, for a grounded conversation about making thoughtful career decisions when the path you’re on no longer fits.
With more than 35 years of experience and 15 years running her own consultancy, Debra has spent her career negotiating complex agreements, advising clients on how to prepare for negotiations, and teaching professionals how to think clearly under pressure. She shares what it looked like to leave a prestigious role intentionally, without panic or financial chaos, and why taking time to work through both the emotional and practical sides of a decision matters.
We talk about what it really means to be ready to walk away, how to evaluate your options before making a move, and why exploring flexibility inside your current role is often the smartest place to start. This episode is about discernment, timing, and making career decisions you can stand behind later.
If you’re accomplished, capable, and quietly questioning whether your current setup still makes sense, this conversation offers perspective, language, and a steadier way forward.
What You’ll Hear
✔️ What a BATNA is and why it matters when you are thinking about a career move
✔️ How to approach a conversation with your current employer when you are considering a pivot
✔️ What it really means to be ready to walk away, and why that clarity gives you leverage even if you stay
✔️ How Debra transitioned out of a prestigious role without financial chaos
✔️ Why being willing to say yes before you feel ready can open unexpected doors
“You are in your strongest negotiating position when you’re genuinely prepared to walk away.”
If this episode gave you language for conversations you’ve been avoiding, share it with someone who needs a smarter way to approach their next move.
Grab your free Heart-Aligned Career Transition Starter at
👉 https://www.leadintact.com/freebies/heart-aligned-career
And if you want support navigating your own pivot — strategically and sustainably — book a free 20-minute call here:
👉 https://leadintactwithlaura.as.me/free-consultation
To connect with Debra Osofsky, find her on LinkedIn or email her directly at debraosofsky@gmail.com.
Success should feel good — and make sense.
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You are listening to the pivot point where we unpack the defining moments that shift careers and lives. I'm your host, Laura Dionisio, a founder of Lead Intact, and my mission is to spotlight the raw real stories behind career pivots, the fears, the hopes. The messy middles and the bold decisions that follow if you're feeling stuck or quietly wondering what's next?
I hope these stories help you see yourself a little more clearly and inspire you to start moving toward your own dream life. Let's begin.
Laura D: . Deborah to the Pivot Point Podcast. Thank you so much for being here. How are you today?
Debra Osofsky: I am delighted to be here and all, all is well.
Laura D: I love it. We were just chatting before we hit record. You're in for a treat. I had to like pause Deborah. 'cause I'm like, no, no, no. We have to record this because already you are giving some gems that I think everyone who's listening right now could, could really learn from, not just from me.
Laura D: But before we get started, I'm gonna read Deborah's very impressive bio. Debra Osofsky is a deeply experienced negotiator and contract expert, a formidable attorney, and a highly engaging trainer. With more than 35 years of experience. negotiates on behalf of clients and advises clients how to improve their skills to effectively prepare for negotiations, negotiate great deals, and draft clear contract language. Debra has been running her own consultancy for 15 years offering clients. Expert negotiating assistance. She leads negotiating teams of all sizes and composition in structured and unstructured scenarios, and also engages as an advocate in one-on-one negotiations. times, Debra assists clients as a negotiation whisper.
Laura D: I love that we're gonna talk about that. Helping them in challenging circumstances to refine their negotiating strategy, create and respond to proposals and reach successful agreements, all while remaining invisible and allowing the client to take public credit. Love that too. Debra regularly teaches in Cornell University's public programs and in virtual and onsite professional education programs independently and through Marcus Evans, including fundamentals of negotiation. bargaining and agreement writing. Debra received an undergraduate degree from Cornell University and a juris doctor from Harvard Law School. She's really smart years of experience as a litigator, as well as a negotiator. Allow her to utilize adversarial and collaborative modes of problem solving, whichever is appropriate to the circumstances, and to help others to strengthen their ability to do the same. Wow. That's amazing.
Debra Osofsky: you.
Laura D: know what? I am, I am like, I'll tell you the things that really stood out to me. Negotiation whisperer. I would like to know more about that. And I love how you said allow her to utilize adversarial and collaborative modes of problem solving.
Laura D: So let's, let's talk about that. What is a negotiation whisperer and what do you mean
Debra Osofsky: so right. So.
Laura D: Okay.
Debra Osofsky: so it's important for me to make it clear for people in negotiations. You either have a collaborative negotiation or competitive negotiation. Some negotiations are a mix of competitive and collaborative, but the competitive is kind of a very aggressive negotiation where for me to win you must lose, right?
Debra Osofsky: And that I must, I must beat you. And try to get every last penny out of you every last. A bit of value from you that's a competitive or adversarial or traditional negotiation that's on one side. On the other side are collaborative negotiations. In a collaborative negotiation. Um, we're often, we might call it interest-based negotiation or problem solving negotiation, where the goal of the negotiation is to try to find solutions.
Debra Osofsky: Where I definitely get what I want or as close to what I want as I can, or as much as I can get. But also I'm perfectly happy for you to get something. And in fact, um, we might try to solve my problems and your problems and both of us be successful and to try to find ways even that we can, the collaboration can allow us to both be successful.
Debra Osofsky: Sometimes redistributing between us what one of us cares more about and the other cares less about. And so, sometimes. Collaborative negotiations make perfect sense. Sometimes competitive negotiations make perfect sense and a lot of what I spend my time working with people on is what kind of negotiation are you in?
Debra Osofsky: Whether you should be collaborative or competitive, or at what portion or what pieces of a negotiation should you be collaborative or competitive? If you create a huge amount of value between two people, if you and I start something together and we create lots of value, we still have to divide.
Debra Osofsky: The profits, the value that comes out of it. So there tend to, we tend to go back and forth, even in a collaborative negotiation. Sometimes we go to competitive and being sensitive to when should you be doing one or the other. And I spent a lot of time training people on this one-on-one and teaching this in classes.
Debra Osofsky: And so yes, I spent years as a litigator, um, which is about as adversarial as you get. So if somebody needs me to come in and help them, beat the heck outta the other person, I will do that. But my personal goal is whenever it is available, let us try to be collaborative. Because collaborative negotiations tend to create much more value.
Debra Osofsky: People tend to be much more satisfied with the outcomes, and people tend to when they get to a contract or a deal, they tend to follow or obey the deal. They tend to, rather than trying to. Unravel it or undercut the other side. So collaborative negotiations also have the value of being sustainable that people who feel like they've been collaborative, collaborated with and feel that they got value from the deal are much more likely to actually complete the deal as promised in the original negotiation.
Debra Osofsky: And so that's my preference, but. If the other side doesn't wanna be collaborative, we can be adversarial if we need to. And so that's yeah, that's a lot of what I do in much more detail.
Laura D: Okay.
Debra Osofsky: so should I go on to negotiation? Whisper? You wanna hear about that? Or more about collaborative and competitive?
Debra Osofsky: What's good for you?
Laura D: what, I'm already
Debra Osofsky: I.
Laura D: sense, I, I am starting to understand why you're the negotiation whisper. 'cause just the way you describe, like, ID don't know much about negotiation other than negotiating my salary perhaps, but like, so I never think about like. In business or in contracts. I am curious, I'm assuming somebody started calling you the negotiation whisper, is that right?
Debra Osofsky: I had somebody who started calling me a negotiation, asked, asked me to be a negotiation whisperer. There's a dog whisperer. So it's, I think it's just that concept. So, yes. So I started doing negotiation whispering. Actually in kind of a fascinating scenario, an international, actually multinational corporation wanted to take an action within the US in a labor context.
Debra Osofsky: And, the local. Us portions of this corporation were saying we cannot, this will destroy our company. what the multinational corporation wants to do. And I was invited into a room. I felt like I was working with the CIA walk in. All cell phones have to be dropped. I can take no notes.
Debra Osofsky: They would give me no materials. It was all projected on a screen. I could take no notes. I, and they were, and it was pretty intense because it was a confidential. Issue and a corporation needed to know was a major move that they were planning to make. How dangerous was it? On the, you know, kind of on a scale how dangerous and to the extent that I considered it dangerous, what were the dangers?
Debra Osofsky: And so that that happened and then it started happening more,
Laura D: Mm.
Debra Osofsky: people would invite me in sometime in these very clandestine matter of you can come and give us advice and we'll all pretend we never saw each other before. And other instances where on a much more. Ordinary basis, I'll work with people in an employment situation or in a, at a not-for-profit or in a corporation where they're in negotiations and they're stuck and they don't know why, and so I will.
Debra Osofsky: Debrief with them, learn what's going on, make recommendations, and help. And that's, you know, help people to be successful. And nobody will ever know that there was an external person, me helping them figure, figure out how to solve the problem. I don't need glory. I'm, I'm delighted to help people get to better.
Debra Osofsky: Contracts to get to better outcomes, and I don't need my face ever to be seen. And so as a result if someone wants me to come and stand in the front and be the negotiator to be seen in the room, to be seen on the zoom, absolutely can, can do, do, do, will do. But often people. Are uncomfortable or embarrassed.
Debra Osofsky: They don't understand why they haven't been successful in a negotiation and or they simply don't know where to start even on contract you know, their employment negotiations. They don't understand why they're not doing as well as they think they should be, and then helping people to understand how to be successful in negotiations.
Debra Osofsky: And I help them prepare so that they can go and do the work and then be successful. So I negotiation, whisper at some, some fairly sophisticated levels and then some, you know, fairly ordinary. And, but either way, I don't need glory. I love. To help solve the problem and make people more effective, including someone who's trying to be really collaborative and the other side is being competitive against them.
Debra Osofsky: They keep on losing. If you are collaborative, and I am competitive, I will eat your lunch.
Laura D: Hmm.
Debra Osofsky: Right? And so sometimes we have to go against our personalities. A collaborative person has to be competitive. Or a competitive person would be better off being collaborative, and that's how they'll come out with a better outcome.
Debra Osofsky: And often people don't know because there's no one to tell them. You know, you might not be matching your negotiation style to the actual negotiation issue in front of you. And so I whisper.
Laura D: love
Debra Osofsky: And if I need to, you know, whisper when we need to, we whisper there. And if I need to in other context, not whisper, then I can also get loud.
Debra Osofsky: But I find it much more effective to speak reasonably with people if I can.
Laura D: Yeah, I, I love this, Debra. And you know what's fascinating to me is, is when you started explaining how the negotiation whisperer, phrase, came about, it
Debra Osofsky: I.
Laura D: correct me if I'm wrong, but you didn't always have your own consultancy agency, you said, like, it's just started happening.
Laura D: You started getting invited to these types of meetings and, and it seems like it started as word of mouth. So can you walk us through what were you doing before. how did you realize like, oh, I can actually be a niche in this negotiation things, and then how did it go from there to then starting your own thing?
Debra Osofsky: Right, so it's a great question. I worked as a private. Law firm attorney. I, I went to law school. I took the bar. I practiced as a, uh, as an attorney in a private law firm doing business negotiations, uh, real estate, a lot of real estate transactions. I had a small portion of my work was airlines.
Debra Osofsky: I did some airline commercial, airline work, uh, aircraft work. And then, uh. My, I switched to Airline Pilots Association and I ended up working with the Airline Pilots Association for 10 years, and I did a lot of collective bargaining kind of negotiations, labor and employment negotiations. Worked at other ran faculty union at University of Medicine and Dentistry of New Jersey.
Debra Osofsky: I then went to a job that was a very. impressive job. I think similar to the one I hear, I hear from you and I see in your materials that a lot of the people that you work with are people who get to a job and say, I have the job I always dreamed of. So I was the director of news and broadcast for the, american Federation of Television and Radio Artists, which is now SAG aftra. I had a job that if you had told me 15 years earlier, what would you like, could you, would you, you know, what would you choose? I'd say, I want that one. And so I was in a job that I thought was. Really fabulous. And it was really great in a lot of ways.
Debra Osofsky: I was able to be relevant for news broadcasters and all of radio, radio DJs. I had a very big portfolio. It was very exciting work. I had wonderful colleagues. I loved the mission of, uh, of aftra. There was a lot that was really great about it. Uh, and.
Debra Osofsky: I felt like I had, uh, no control over my work life, that I was endlessly putting out fires and that my work hours were more than I wanted. They were required by the job. I did try to. Rearrange the job descriptions so that I could have some more flexibility for myself. But I wasn't able to get to that place and I also felt like I was often.
Debra Osofsky: You know, the fireman position, firefighter position where you're putting out fires rather than on mission, rather than fixing problems and making things better. We did make some things better, and I'm very proud of the things I was able to do, but way too much of my time was taken over with solving problems that I felt, or, or I'm taking over with tasks that, popped on my desk.
Debra Osofsky: You know, I was supposed to spend my day trying to figure out policy and instead I was dealing with immediate needs and not thought work. And I wanted, so a combination of things, both as to work and as to personal life. Uh, I wanted to have more control over both my time working and my time off.
Debra Osofsky: And also, the kind of work that I did. I had a fabulous job, but I and I had to think really hard about moving.
Debra Osofsky: And I guess, uh, as to tips for your listeners, um, one of the tips I would want to give is it can be very hard to leave that job that looks really fabulous to you and to others. It's hard to explain to ourselves, nevermind other people, why would I walk away from this job?
Debra Osofsky: This is the job. People get in them and they stay for the rest of their lives. And so I, I think finding finding a way to work through that question, whether it's with a therapist or a spouse a work group, um, a group of like-minded friends whether you meditate, right? Finding a way to think, understand that it's a.
Debra Osofsky: That there's an emotional component, um, and a psychological component so that you don't regret the move later. To move deliberately through the process. Thoughtfully, carefully, you know making, vision boards or pros and cons lists, but taking the time to work through the process so you understand not just what you're leaving, but what are the options for what you're going to and understand emotionally.
Debra Osofsky: Lots of people will give you pushback and a remarkable number of people will say. Why are you doing this? Wait, you left this job with this money and this prestige, and isn't this what you work for? And so understanding really well, working through it the way that is appropriate, uh, to work through it and to give it some time.
Debra Osofsky: I don't recommend the take this job and shove it approach, not in anger one day, but through very careful thought and deliberation. And then I'm gonna say from a negotiating standpoint. If you're in a job and it's not working for you and you're visioning what you might wanna do next to me, the first stop is to your current employer to say to the current employer, this is how I feel.
Debra Osofsky: This is what I'm interested in, and can you structure work for me that will make this. That, that will be useful. In other words, if you, if your issue is you simply want to spend half the year cycling and the other half working as a chemical engineer, probably your employer is gonna say no. But if you're planning on doing that anyway, say to your employer, I understand this is not typical, but this is what I'd like.
Debra Osofsky: Can we work it out? And, you know, you're in your best position to negotiate when you're ready to walk away. Truly. Then why not raise that question to suggest how it could work? Right. I would love to do this, but I also wanna, I had a colleague once who wanted, took a cooking class in France and wanted a, a, a long-term cooking class and wanted to work at night and so on before, it was, before Zoom was before COVID, before everybody zoomed from everywhere said, look, I wanna be able to do this.
Debra Osofsky: Can you accommodate me? And so there is a value of asking where you are, but I am gonna say as a tip to your listeners understand that it's a big emotional move and, and a approaching it with thoughtful deliberation. Your emotions, your emotions are real. Your feeling about it is real. If you're uncomfortable and you think there's something to address, there probably is, right?
Debra Osofsky: But that doesn't mean that the how to handle it is purely emotional. And use your resources, therapist, religious counselor, parents, friends, siblings, colleagues, whoever figure it out and work it through as a process. Think about it so that. If you have a hard time, two or three or six or months in or a year in or whatever, go, oh, but I made this decision thoughtfully, carefully, reasonably.
Laura D: Deborah. That's so good. That's so good. I'm just gonna
Debra Osofsky: Okay. I'm glad.
Laura D: What I wrote from what you said is move deliberately, thoughtfully, carefully, acknowledge your emotions make use of your support, tools you have, like meditation and such. And this one, I think my listeners would really appreciate this. The best position to negotiate is when you're ready walk away.
Laura D: Can you talk a little bit more about that? I am thinking of the listener who was so, like exactly what you're saying. Maybe they're burnt out, maybe they were passionate about the job, but they keep being firefighters instead of doing like the thought work. But then they, maybe they feel a little stuck though, like the thought that you were just saying, but I've worked so hard to be here. This was my dream job. Imagine a listener like that, and it sounds like the thing to do, like you said, is
Debra Osofsky: Yeah.
Laura D: to manager. What would you say to a listener who is exactly in that position feeling that way?
Debra Osofsky: Right. So I'd say the first step is to have an actual real life alternative. We call it in negotiations, A batna, a best alternative to a negotiated agreement. So BATNA is the language. And what that means is, so for example, if you're negotiating over salary with your job, if you have another offer from another place for a higher salary and a better job, that's why.
Debra Osofsky: You know, people say, well, I've been, I had a headhunter, I don't call them, but a headhunter called me and told me I could have a job at such and such organization with such and such salary, and you bring that into your employer to get a better offer if it's a real job that you would go to. Sometimes if you say that to your boss, they say.
Debra Osofsky: I hear that, and that's really great. And if you wanna leave, you can leave. And so we, this is not a bluff, this is not, we don't do it if we're bluffing, but we do it when we've really thought about what we want to do and if we're leaving for another job, or if we have already saved our money and have our nest egg and are ready economically to move.
Debra Osofsky: And we have a plan for what we will do if we simply turn, you know, turn that key and leave when you are ready. For that, when you really have a re truly ready to leave and have another alternative so that if your boss says, that's all very interesting. It's been nice knowing you that you are happy. It isn't a bluff.
Debra Osofsky: You really right. We're ready to leave. But you go to your boss and you say, look, I'd really, I really love working at this organization and here's what, here's, I really love to work here. I, I'm planning on this other alternative, but I wanna give you a shot to try to work this out. I can work with still at my organization, but here are the things that I need.
Debra Osofsky: And then to be very clear what that is, clear about what it is, and clear about where the flex points are and aren't. Right. The I'd like to work fewer hours overall. I have my current, I've been working 70 hours a week. Um, here, here's my records that show that this is what I'm working, um, I would be interested in.
Debra Osofsky: I'm happy to continue working, but I want to be able to do that. Really not, you know, between 40 and 50 a week, right? Or some weeks might be 70, but I want an average over the course of the full year where I'm fine to work during tax season or whatever. Extremely busy. But when we're not busy, I wanna be able to work from Portugal.
Debra Osofsky: Right. Whatever it is that could work for you to talk about what those options would be and always to think ahead about what it is that the other party would want. When you think about, they're just gonna say no. Well, what is the hesitation and concern that they have? Right? So if the concern is, well, yes, we could say yes to that, but what about the week that we are in convention?
Debra Osofsky: We need you there. Okay. I can tell you ahead, I know convention is always an issue. I can tell you that even though I wanna work this or that, or be from Portugal, I'll come back from Portugal, right to, to anticipate. When you hear the no from your employer in your head, don't stop at the no. Go to the, why are they concerned and what are the things that I might be able to offer that I can get what I want and solve the problems that.
Debra Osofsky: That my manager's gonna be concerned about. Yes, that could work. But what about this client who, whatever, whatever you hear, think about how you can get what you want. They can get what they want. Even if that means sometimes we do it this way, sometimes we do it that way, right? On 30 weeks outta the year, we'll do it this year this way.
Debra Osofsky: But you know, the other 22, you know, we'll do it the other way. So thinking about what your boss will be concerned about and then coming up with some solutions and being open enough to say, look, you know, this is, I see these at your issues. And also to say, once they're saying no. I hear you, but tell me why that, where there's a no, and also be ready that, you know, you may be leaving and you may really be leaving, but take your swing at it.
Debra Osofsky: It's a great moment to negotiate when you're really ready to leave.
Debra Osofsky: And a lot of people have an emotional problem with that. They're like, I just spent all this energy to getting emotionally ready to leave and now I'm gonna go have a conversation with my boss. The answer is, yeah, because if you can get what you want.
Debra Osofsky: Without taking the risks of going out on your own, if you really can get what you want, give it a shot or even plan. Look, let's give it a shot. If your management says yes, you also wanna put a limit on it. You wanna say to yourself. I'm trying this for a year. That's what they're saying to themselves as well.
Debra Osofsky: They're only trying it out to see if it works. Even if they say yes, they're just trying it out. And you could try it out and say, we thought it was gonna work, but it didn't really, and then be ready at the end of the three months, six months, year of the, you know, of the tryout period. So I, but I do think it's a great moment to negotiate.
Debra Osofsky: Yes. And, and, you know, I help people do those negotiations. I've helped many people do those negotiations.
Debra Osofsky: Um, sometimes even just as a segue that it's not even meant to be a permanent job, but that they're doing, they're working on an important project. I don't wanna leave now because we're in a five year project and Right.
Debra Osofsky: I wanna be able to stay with it until it's done well, you could make an arrangement where you change from a full-time employee status to a consultant status. That allows you, that could almost be perfect, right, where you, if you are trying to build a new business that you work for your previous employer.
Debra Osofsky: First 70% time, then 60, then 50, then 40. And that decline from your current employer allows you to build a new practice or a new idea of your own. So it doesn't have to be a sharp break. It might be, but it doesn't have to be
Laura D: that.
Debra Osofsky: better chance, often with, with that, with a small and medium sized corporation, right.
Debra Osofsky: Or business. Corp. You know, big, big corporations sometimes are like, oh, we'll just get another one to replace you. But there's, there's opportunities to do it. And I've seen people negotiate for a different work life, either in the long term or for a a, a temporary period. Temporary sometimes in years.
Laura D: Deborah, like, I honestly,
Debra Osofsky: else?
Laura D: you know what's crazy?
Laura D: I feel like I could end the episode here, I won't because I still wanna ask at least one more question. Like,
Debra Osofsky: Okay.
Laura D: was so helpful and I, I wish I'd known you like, when did I nego like three, three years ago? Because they probably would've shortened the time.
Laura D: What I'm hearing is be clear, be prepared, and be ready if you need to leave. What I love that I didn't even think of is the mind shift of like a tryout period. You know, you may not say that, you know.
Laura D: To the manager, but like, that didn't
Debra Osofsky: Right.
Laura D: occur to me. And I'm sure this has been true for the clients you've worked with, but at least for me, sometimes I get into that mindset of all or nothing that if I decide to stay with this company, that means whatever other alternative I was thinking is forever gone.
Laura D: And I just love that you said no, it could be a, a tryout period. So
Debra Osofsky: Right.
Laura D: yeah. Thank you. I. Yeah.
Debra Osofsky: Yeah.
Laura D: That's so good. I wanna shift over because aside from like the negotiation stuff, like the part that we were talking about before, listeners, I'm telling you Deborah has a lot, a lot to say. I'll give resources on how to contact her in the show notes.
Laura D: Don't worry. Everyone's like, stop talking, Laura. Let her talk. Would love to hear more about, because.
Laura D: You mentioned you started off like in broadcasting and then you were a lawyer, and then you became the negotiation whisperer. What was that shift like for you?
Laura D: Talk us through what that was
Debra Osofsky: Right. So I'll talk about that. So the shift, so I made my decision when I was at, uh, was the National Director of News and broadcast for aftra. I made my decision that I wanted to move. I did have the conversation where I was and. What it led to is a very long notice period because I was involved in some very time sensitive matters and I didn't want to leave AFTRA and the people I had worked with in the lurch.
Debra Osofsky: And so I. I think from the time that we decided that I wasn't going to stay, it was more than six months where I was finishing up work. And so for me that was emotionally, I was able to begin thinking about what I wanted to do next.
Laura D: Hmm.
Debra Osofsky: we did something quite valuable. And this is, I would say, uh, you know, maybe a tip to your listeners as well.
Debra Osofsky: We created some economic stability in my house. My husband, I've my husband's still married to him. Our daughter who's now 26, was at the time, let's see, 10 years old actually. Uh, and so we, my income was relevant in our family, and so we created, uh, we decided we, we were gonna refinance our, our house anyway.
Debra Osofsky: We took a year of my W2 out of, um. Out of the house and we decided that I would have a year sabbatical. My husband is a professor, so we decided I had never had a sabbatical. We were gonna create a family sabbatical for me to be able to economically do this, we could have done it other ways. We had, you know, whether people save money.
Debra Osofsky: I've, I've known people who've moved back in with their family, or they've moved into different living arrangements to save money. To have the economic base to be able to try out something new. But having, uh, we created an economic environment and I thought I was going to, I was debating how I wanted to work.
Debra Osofsky: Um, I, I thought I was going to do a lot more work on. Advising on contracts. It took a long time for that part of my practice to build. And at the beginning I did a lot of project work.
Debra Osofsky: So I haven't, I've been doing project work now for 15 years, project work or work for individual clients now for 15 years.
Debra Osofsky: At the beginning, I found pieces of work that. Gave me some stability. So for example, there was a union that was reorganizing itself and I worked with them two days a week. For about 18 months. That was perfect for me. I had two days of steady income, right? And then I had other, and I also started teaching a class at Rutgers.
Debra Osofsky: That was my first place I wanted to teach. I taught at Rutgers, then I started teaching with Cornell. But essentially little by little I built my my practice from lots of different pieces. And so. It was not all at once. The part about having that initial kind of two days a week steady work that I could rely on for 18 months was very useful.
Debra Osofsky: Um, and when I was done with that, I had, um, another kind of term project that I assisted another organization I made a website. And I started literally just telling people what I did. Anybody who works knows in, in a consulting capacity.
Debra Osofsky: The way work, one of the big ways work comes is you do work and you get more work. You are out there in front of people you present. Teaching is very useful for this. Teaching often doesn't pay enough on its own, although I've done relatively well that way. But teaching but puts you in front of.
Debra Osofsky: Audiences that can then hire you to do other things. And also following the work.
Debra Osofsky: So the negotiation whisperer, I didn't say when I left my television radio artist job, oh, I'll be a negotiation whisperer. I said, I wanna do meaningful work. I wanna be able to use my, uh, negotiation skills, my teaching skills in a way that is valuable for me, um, and for the world.
Debra Osofsky: I hope for other people. And I did expect to be in rooms. Uh, with my face showing, but I never expected that I'd be whispering to people in the negotiation context. And yet that's a valuable part. And some things I do are very public. I was just helping to facilitate negotiations at, um, Kaiser Permanente, a very public, I was in front of giant conference rooms of people, um, helping to facilitate negotiation.
Debra Osofsky: So I'm perfectly happy to have my face shown, but I think. Sometimes the work finds us. Like I went, I was, uh, uh, work, working with a friend of mine and a colleague, uh, on, uh, sexual harassment training because people always need training on sexual harassment, and it's a thing that I can always do. And the person I was working with was an internal investigator and during the Me Too movement, um, and Black Lives Matter.
Debra Osofsky: She said to me, I was talking to her about, well, what other, what class should we do? And she said, actually, I want you to be an investigator. And I said, I'm not really, let's talk about that. And I was somewhat hesitant, but it was great and interesting work and feed some of my other work. And I can give value and get value.
Debra Osofsky: So sometimes the things we think are gonna be our economic mainstay aren't always what we expect. But if it works, if somebody else says to you, I'd like, I think you could do this. I'd like you to do this. Try to believe them. Try to say yes. Right. A lot of, I've seen people say, oh no, I don't do that.
Debra Osofsky: You're like, if this person thinks I can, let's talk about, be honest to say, look, I haven't done an investigation since I've, you know, X years ago. You know, I haven't done it. I can. How can we study up? How can I make sure that I'll be able to give you good value? Right? But say, yes, somebody comes and offers you work for pay.
Debra Osofsky: They're willing to pay you for work. They must see something about you. Try to say yes. Think about saying yes, but I did build, I have done a lot of different parts. I do negotiations. I do them publicly and privately. I do facilitation publicly and privately. I advise individuals publicly and privately, right?
Debra Osofsky: It's a. And I do a lot of teaching in different contexts and some of it in labor and employment and some of it in pure business. My Marcus Evans work Pure Business Negotiations, because I got a, I got a contact from somebody who said, can you teach this? I said, well, I haven't taught the Uniform Commercial Code.
Debra Osofsky: You know, ever, but 90% of what you're asking, I can teach and I can learn what I need to about the Uniform Commercial code. So yes, let's do that. And then you do that work and then more work comes because you did that work and somebody else sees you and then they invite you. , I'm not sure I fully understand the magic of it, but my husband and I sat down and made a boogie.
Debra Osofsky: You know how much I have to get. Boogie or bogey, maybe it's a bogey like, and a amount of money I'm supposed to make every year to keep up my side of the bargain in our relationship. And I have, I made it every year, including COVID kind of amazingly.
Laura D: Oh my gosh.
Laura D: Amazing.
Debra Osofsky: so, but, so that's okay. So, and, but not always from the sources I expect, but that's okay.
Debra Osofsky: It meets my goals. My goals when I left was more control over my life and interesting work to do. And I spend like more than six weeks a year on vacation. sometimes eight or 10 weeks on vacation a year. I have a lot of vacation time because I make it for myself, and then the other time I do really good and interesting work.
Debra Osofsky: So does that answer your question or maybe not enough background? Okay.
Laura D: I'm smiling. So like, you
Debra Osofsky: Okay.
Laura D: like taking all these notes?
Debra Osofsky: Okay. That was a lot. You got a lot of notes.
Laura D: good. Okay. I'm gonna, I'm gonna tell you the, the things that, like, you're, you are amazing. I'm so glad that we. We connected seriously. So the first thing that I wrote down is you had an economic plan. Because a lot of the times when I have my own clients or even like friends who talk to me and they wanna switch, they wanna corporate or they wanna whatever, even if they wanna stay in corporate. And the concern is always the money. I can't, I can't leave, I'm stuck. But what I love is you're like, well then create an economic plan, whatever that looks like.
Laura D: And then you gave an example of what that could look like. And then what I really loved is you said your goal. had two goals, more control of life, interesting work to do. You did not say, my goal is to become a negotiation whisper. Like you, you weren't attached to a specific, this is what I teach. You weren't attached to a specific how and then you said be open to what it could look like. And the thing that, like really in our conversation that wasn't recorded here, but I'm glad it came up again when you said, when if somebody offers you something, 'cause they see not offers, but like asks you to do some sort sort of work. I love that you said, really, let's talk about it. You know, you said try to say yes.
Laura D: How can I say yes? Right. So when you said that to me, I'm like, oh, that's so good. And, and Debra like that happened. I like, somebody was like, I'd like to work with you, but like the package you're telling me isn't exactly it. And at first I'm like, oh, I don't know. But then I thought about it and we had our conversation and then I was like, what am I doing?
Laura D: Saying no to money. So then I went back and said, you know what? Like, I'm, I'm gonna make a special offer because, you know, like I, I can tell that you really wanna work with me and here. So then I proposed something that was not my plan. So I love everything that you said. And then you said you work then you get more work.
Laura D: So for my listeners who maybe relate to me who are sometimes like, I wanna do the quote unquote right thing and get into analysis paralysis, it's like, no, get out there and do something. 'cause it's gonna lead to the other thing.
Debra Osofsky: Right. And the something leads to the other thing and, and, and the saying, yes, I do remind another one. I had somebody early on when I was on my own, uh, I was teaching negotiations and somebody said, oh, can you teach mediation? And I immediately, it was. It's connected. It's one step over maybe for people who aren't in media in negotiations, it's all the same, but it's one step from what I was doing.
Debra Osofsky: And I said, yeah, I think I can do that. Let me, let me, uh, let me think about that and get back to you tomorrow. And I quick got on the phone and called a friend of mine who's a mediator and said, would you like to co-teach this class with me? And then. I co-teach the class. I say, I come back. Yes, we'll do that.
Debra Osofsky: I'm getting paid a little bit less because now I can only, you know, they offered me a certain amount and so we're all that economics about how that works out. But okay, make a little bit less money, but I'm going to teach the class and then I learn things 'cause I co-teach. And now one of the parts of my practice is to be a mediator and facilitator, partially because I've taught a class in mediation.
Debra Osofsky: Partial because I said yes, because I said yes because we got there.
Debra Osofsky: I'm also gonna say sometimes the economic base is something else. I had a my cohort when I first was trying to figure out how to move from being a salaried employee to making my own money, I had a lot of conversations with. Largely women.
Debra Osofsky: ' cause I did feel like that men have a lot, learn a lot from men as well. But also I had a, a, a, a particular cohort of women because I, I think that, um, sometimes we see things in a more open way. Uh, but I had one friend who literally was a summer wedding photographer. And that was the base of money that she had while she was trying to become an arbitrator.
Debra Osofsky: And she was never credited. She didn't, she didn't put out, she wasn't on a website, but she was a, she had been a wedding photographer and in the summertime, they need lots of wedding photographers. So she would do it and it would make her X thousand dollars a year. It had nothing to do with her career goals, but it was a guaranteed amount of money.
Debra Osofsky: And she did it for a long time until. Her cash flow from the, the work of her heart came across right, and there's no shame in doing that. Or , , another friend and colleague who was the bookkeeper for a small New Jersey town. It pays X thousand a year. It takes a certain amount of time.
Debra Osofsky: It's a guaranteed amount of money. And while you're trying to build the, the career of your dreams, the job of your dreams, the consulting firm of your dreams, it's okay to do these things. It doesn't all have to be on point towards your goal. Some of it is. Um, helping you emotionally deal with the question of how is my rent or mortgage gonna be paid?
Debra Osofsky: And that's legitimate and you can do that and nobody has to know. You can either put it on your resume or not that you are a wedding photographer or are the town bookkeeper for the town of x New Jersey. And that's okay. And then, but over time, you do wanna get in the spaces where people hire for the work that you do, so that over time people will hire you for the work that you want to do.
Debra Osofsky: That feeds your soul, that makes your heart happy, and also allows you to have SEP contributions to your own retirement, which. You hope one day to still be able to do right, because you, you wanna have your life, you want your current economics to work, and eventually you'll start needing to save again for your own retirement.
Debra Osofsky: Maybe not in the first year or two that you're out on your own, unless you're really great, but you, yeah, you need to be able to do that.
Laura D: Debra, this has been so good, and I honestly can probably talk to you for another hour. No, I'm like
Debra Osofsky: But your, your listeners are like enough already.
Laura D: no, no, no. They're like. I want to talk to Deborah.
Laura D: So for those who are just like, oh my God, I, I really need someone to help me negotiate, like whatever it is or who, who just wanna get in contact with you.
Laura D: How can people find you? How can they connect with you?
Debra Osofsky: Okay, so the best bet, I think LinkedIn is a great place if they're on LinkedIn. I am there. Um, I'm also fine to get an email if you send me an email to Deborah osofsky@gmail.com. Shall I spell that or do you have me, do you have it in your notes so that people can grab it?
Laura D: show notes.
Debra Osofsky: They will put in the notes.
Debra Osofsky: Okay. So, and, and that's fine if the, uh, people can get in touch with me. And I also will say this if I can't, if people are interested in negotiation assistance obviously right, I have fees that I charge. But my first initial conversation, uh, is always free so that I can learn what people need and also.
Debra Osofsky: I endeavor if I cannot help someone to see if I can send them to someone else. It's one of my theories in the world, which is I think that the world of negotiations can be intimidating and confusing to people. The words of, you know, law can be intimidating and confusing, and if, if it's not my area, I often can help people figure out.
Debra Osofsky: How to find the right person to help them. So I'm, and I'm open to being contacted by whoever your listeners are, because you are glorious and the service that you're providing. I think this idea of that pivot moment that you are, I, I'm very taken. I mean, this is why I'm talking to you, is, is that. I really wish that when I had been at my moment where I was trying to sort through this question, I was not aware of anybody like you who could help to advise and you know, manage the process, think about the process.
Debra Osofsky: And so, uh, I did. Tried to talk to career counselors who really wanted to send me back to a, a paid career with someone else. Like, let me find you a job in a corporation or a labor union, or a not-for-profit. And I was like, no, that's not what I want. And I, I didn't want a battery of tests that wa I wanted someone who wanted to help me do the thing that I already was pretty clear that I wanted to do.
Debra Osofsky: Help me kind of double check it. And so you seem to be. In the niche that I really wish I had had, I had been able to meet you, um, 17 years ago, but I get to meet you now, so that's great.
Laura D: yes. Thank you so much Debra.
Laura D: And I have one last question that I ask all my guests.
Debra Osofsky: Sure. Okay.
Laura D: this is a fun question. If you are an item in a coffee shop, so you could be a drink or a pastry or whatever it may be, what would you be and why? I.
Debra Osofsky: so I love Earl Gray Tea. I will have, they do a London Fog, which is kind of, you know, a, a a a, a high tone version of that. But Earl Gray Tea with milk, I love Earl Gray Tea for the, the flavor of it, the scent of it. And I'm also really taken when I learned the backstory of Earl Gray Tea or of Bergamot, which is the flavor in Earl Gray Tea.
Debra Osofsky: And that is. Bergamot is a flavor that comes from the rind of a bergamot orange. A bergamot orange. You cannot eat. It is too bitter to eat a bergamot orange, but. There's essential oils in the rind, and that essential oil is the scent of Earl Gray Tea. And I love that somebody figured out that you can't eat the fruit, but that the oil in the rind is gonna make this glorious scented tea.
Debra Osofsky: So I, I, I think, I, I think that. It, it doubles my pleasure in that this is an item that you kind of, how did it come to exist and I kind of love it, but the scent of Earl Gray Tea and a really good Earl Gray tea with lots of milk and sugar. Yay. I love that.
Laura D: I love that. And you know, I didn't know the story first of all, behind the scent, and I love that it, it kind of. It is like a great analogy for what you were saying about being open and like, you know, like, like say, a way to say yes. It's a great analogy. So I think that's a perfectly fitting item. You didn't even intend for that, but like, that's what I'm seeing in that.
Debra Osofsky: Oh yes. Well, right. Somebody, somebody else said yes or somebody else was thinking outside of the box. But I think that the saying, I think the saying yes is, is really important. I think that particularly when we have areas of expertise, if someone is, An engineer or a lawyer, um, if they have a specific profession, a doctor, they have been taught that there are boundaries and that we should say yes to this and then no to the things outside of there and.
Debra Osofsky: Those categories can be very useful to find the expertise that you want. And you know, I, I wanna go see a doctor who has a lot of expertise if I need to see that doctor or a lawyer or an engineer, right? If I wanna build my building safe. But when we are thinking of our own lives and how we want. To live our lives and the work that we want to do.
Debra Osofsky: We don't have to be so tied in on, on those on those categories. We're allowed to be on the edges or adjacent or maybe even a couple of steps over from, from before and those opportunities and to be, and I think really to believe people when they say, I'd like you to teach it. 'cause some, I'd like you to teach this class.
Debra Osofsky: I'd like you to do this negotiation. Sometimes we think, why me? Um. And instead to think this person sees in me a person who can do this job. So let me find a way if I can, to do it, if it really is. You know, somebody wants me to argue a divorce case. I'm not doing that because I don't have the expertise and I'll be happy to refer them elsewhere.
Debra Osofsky: But if it, if it can work, yeah. Say, say yes. Find a way to say yes. I think that that's, and yes, if my tea, my, my drink choice is, uh, double, you know, doubles up on the idea that I'm gonna say yes person. But yes, you should. I, I'm gonna say, I dunno if you can, if you wanna, it's in or out of your podcast, but there is a podcast, called Gastropod, that's all about food. And I learned a bunch about this from Gastropod. It's two women who, who talk about food, food science food history, and if you like food like I do it's another podcast. I learned it there and, uh, it's pretty fun. So anyway, anything, I think it was your last question, so
Laura D: that,
Debra Osofsky: I really am so
Laura D: Thank
Debra Osofsky: delighted that you invited me. So thank you. Thank you for having me and asking such good questions
Laura D: you so much, Deborah.
Debra Osofsky: Okay? All right. Take care now.
Big thanks again to Deborah Osofsky for sharing their story so openly. These conversations are such a reminder that no pivot is too messy, too late, or too unconventional. If something she said resonated, don't keep it to yourself. Share this episode with someone you know. Who needs it, and when you are ready to start your own pivot, head to www.leadintact.com or free resources or book a free 20 minute call with me.
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