Getting Career Clarity in Uncertain Times

Career clarity in volatile professional environments requires a shift from traditional, linear career models toward intentional self-reflection and experimental planning. The primary challenge addressed is the obsolescence of the "company as family" model and the difficulty of obtaining actionable advice in a globalized, rapidly changing job market where automation and disruptive technologies frequently alter professional requirements.

The approach utilizes a series of structured reflection frameworks to decouple perceived wants from actual needs. The first technique, the Five Whys, adapts a system reliability engineering post-mortem method to career goals. By iteratively asking "why" a specific objective is important, individuals move past superficial desires to identify core needs. This is followed by Odyssey Planning, a method from the Designing Your Life framework. Participants map three distinct two-year trajectories: a continuation of the current path, an alternative path necessitated by a sudden disruption (such as a layoff or automation), and a "wildcard" path assuming unlimited financial resources.

Key takeaways emphasize the importance of identifying behavioral blockers—habits or tasks that align with a past version of the self but hinder the desired future trajectory. The process concludes with the creation of a concrete action plan with deadlines to avoid "autopilot" mode. Additionally, the concept of the Data Diplomat highlights that for technical professionals in leadership or data-centric roles, diplomacy and stakeholder management are as critical to career progression as technical proficiency.

This description was generated by Open-Source AI using the transcript of the session and the original submission contents.

This session took place in track Education, Career & Life.

Submission

The proposal as submitted by the speaker before the conference.

The data & AI field is evolving faster than ever. New tools, new roles, and constant “next big things” can make even experienced professionals feel unsure about where they are heading, and how to make intentional career decisions in the middle of all this change.

You might be doing well, feeling comfortable. Interesting work, steady progress, recognition. And still, there’s that question in the background: Where is this actually going?

A lot of career advice in tech assumes there is a clear path to follow. In reality, most data & AI careers don’t work that way. Roles shift, organisations change, and what used to feel like a logical next step often isn’t anymore.

In this workshop, we’ll slow things down and focus on direction rather than decisions. The goal is not to figure out “the next job”, but to get clearer on the kind of work you want to do.

This is a practical, hands-on session.

We’ll use exercises such as odyssey planning to explore a few possible future paths you could take from here.

You’ll work through: • Different ways your career could evolve • The trade-offs each direction comes with • What feels worth exploring further, and what doesn’t

And, just as importantly, how you feel about these plausible futures.

You’ll leave with a clearer sense of what matters to you now, and a stronger sense of direction

By the end of the session, you will: • Have more clarity about the kind of work and influence you want going forward • See more than one possible future, instead of feeling stuck with a single “right” option • Feel more confident navigating uncertainty without rushing into decisions

Who this session is for • Data & AI professionals with a few years of experience or more • People who feel “in between” stages, roles, or directions • Individual contributors and leaders alike • Anyone who wants more intentionality in their work

Transcript (auto)

Auto-generated from the recording utilizing Open-Source AI. Speaker labels (Speaker 1, Speaker 2) reflect diarization, not identity. Timestamps refer to the recording.

Speaker 1 [00:00]

Everybody, welcome to our next workshop, Getting Career Clarity in Uncertain Times, from Teresa Jovchuk. A big round of applause. Thank you. So, good morning, everybody, and welcome to today's workshop. i just to because there's a lot of people i mean i obviously uncertain times are there for everybody so just a little bit disclaimer this workshop is like very much about self-reflection so if this is not your thing today and you usually you are used to do chat gpt reflection then this is going to be really hard for you, so I do invite you to take the time to stay and do this, but if it's not your vibe today, that's totally fine. There's a lot of AI talks outside. Okay. So maybe for the first question, and there's post-its, and think for yourself while you're Here, maybe just a question for everybody. What are you pretending usually not to know? Maybe take two minutes. That's at work, in life. I can give you an example. At some point, you're the only one who knows how to fix a computer, so it's also very valuable to pretend you don't know how to fix a computer. But maybe at work are things that you pretend not to know so you don't get to do them. I feel like I tend to pretend to know something more than pretending not to know something. So some people say pretending to know more, yeah, that is a very valuable skill to have. I think especially now when everybody, we're navigating, there's a lot more people pretending to know things. And I think sometimes it's also valuable that everybody is aware of that and that we also do it. Jessica? So, a comment from Jessica is that actively pretending not to use coding assistance in in order to not normalise that that's how we should work, or are expected to work, okay? So this is going to be a little bit of moving around in the room, so I hope you are comfortable, but feel free to expect to move around, and if you still want to share what you know with everybody, you can take post-its, and at some point you can write it and put it on the pretending not to know wall for later. And we have more pens. Thank you very much. So a little bit about me. I am coming from Bucharest, which is in Romania, in Europe, and I studied computer science. So I did really do the traditional path to data science, studied computer science, and then did a random PhD in computer science. And then I ended up with that in Germany, And then I somehow stayed. I was not really planning on that either. And I've worked at several companies like Sync, Freenow, and I've been doing a lot of teaching. And then since last year, I've transitioned to freelancing. And one of the things that I do is also leadership and career coaching. And this workshop is from that, from a framework that I developed end of last year called the a data diplomat and this is the phase of that called strategic planning so this is what we're doing today so a little bit of introduction to what is career and I think this is maybe something that we are struggling with addressing sometimes because we are used to career being from everybody in our family that is like a generation older career is this nine to five and a solid paycheck that solves all your life problems and you have safety you have the ways you're working are not really changing um this company as a family is something that kind of died already a decade ago but there are still companies that say we're like a family until they're not and um and honestly the generation before us all they had to do i mean also some of us obviously all we had to do was learn how to use the Internet. That was the most disruptive thing that happened in the last 20 years before five years ago. And now it's like career, you talk to five people, they have different definitions of what career is for them. You cannot just go to a random person and ask for career advice because their life is so different than yours that whatever they tell you is not going to make sense to your life. And we all bring, we have also globalisation, everybody's moving around, so with a migratory background you cannot compare yourself with someone that grew up in the same country as where they're working. So all of these things make it very hard to get actionable career advice for you from a random person. And then we end up having to unlearn everything that we heard and, like, just try to not assume that the things how we expect them to work are how they're going to work. And the world is changing so much faster that our brain usually is not really equipped to deal with that. So take a moment and let yourself be fine with the fact that you're not fine. That's totally normal. You're not supposed to be fine in these times. So basically, today's exercise is a little bit what we're going to do is a little bit trying to let go of whatever path we think we should be on. And just try to experiment with, like, what if we don't do that thing that everybody... Going with the flow, where life takes us now. What if we take a little bit of action to go away from that? So we're going to start with an exercise. It's called the five whys. If you're working in system reliability engineer, you probably know this. You've done postmortems. If you're not, this is a fun exercise. So take a moment. You can have paper. You can use post-its if you don't. So you have everything you need here in front. So try to you can also use electronic format if that works for you. Take five minutes and list five things that you feel like you want to have to have in in your career. And don't overthink it. Just write. It doesn't have to be I'm going to Can you put back the instructions on the screen for the reason my screen disappeared? needs post-its around here. There you go. I will definitely need some of this for the next exercise Does anybody need more time? Thank you. Thank you. We are going to only pick one today, so everybody, if you look at your list, think of which one is the one that you want to explore, and we are going to go into pairs so you can, for For simplicity reason, just turn to the person next to you. If you have someone. If you don't have someone next to you, find someone next to you. Move around. There's some... And people... That's also a very good way to meet new people. And you're going to... We're going to take ten minutes, and you're going to take turns, and you're going to play the game with asking yourself five times, why do you want this? So, and be insistent, you know? So first person says, I want to, you know, become an astronaut, and the other person is like, why is that important to you to become an astronaut? And it's like, I don't know, I always had a dream to go see the stars, and why is that important to you? And continue exploring this until ideally you get to something that is something that the person can say this is something that I really need to have in my life. And then swap roles. And you have We have ten minutes. Find a partner. This is my, like, topic, success, success. So, why is this important to you? Hi. Hi. Sorry. So the exercise now is to take a couple of minutes and write for yourself. do you want to have in your career and then once you're done you you go into an interview mode with each other and you ask yourself why do you want that why is that important why is that important like five times I will shortly put the previous slides so you can take a look. Thank you. Sorry, I just need to take this one. Thank you. Thank you. Thank you. Thank you. So, if you haven't switched yet, this would be a perfect time. Thank you. And the business perspective also. All round and then come up. Thank you. Thank you. Thank you. So, there's one more minute left, so you can slowly wrap it up, and then write it down. I made a wall here where you can place on the wall what is the need to that you why behind all those five questions there's like ideally you got to a point where you have a little bit more clarity on something that you actually need at work and in your life and you can like post it on that wall on the left and ideally you find ways if somebody has the same need you put it next to theirs and then just stay close and maybe we see that there's some common ground or some clusters happening. It is still like a PyCon and PyData conference, so there has to be some data analytics going on. Yeah, these are sticky tapes. And I distributed some also on the sides. So this is the need wall over here. Yeah, that's also fine because that's something that's going to be needed in a second. I'll just put some of the sticky tape in a pen here if someone needs more. There's also Sharpie there, if you need to. Thank you. Thank you. Yes, it was planned in the afternoon, but then the panel was also in the afternoon. There are more sticky notes in the space of the Feminist AI Party, the LAN party. If you are sitting on a pile of sticky notes in your space, please bring them here. And there's more sticky notes here at the front as well. Here's more sticky notes. Yeah. Come with me. Yeah, and the next one is without sticky notes. We have three more minutes left. There's a whole wall. Use the wall. You can also use the fire escape. I so agree with that. Yeah. Yeah, that's... Because I did the... Teresa was doing the coaching. I joined her coaching earlier this year. Oh, cool. Yeah. Maybe a bit early for me, but it was very insightful. No. No. Thank you. What did you get? Very few people left. So, for everybody, this five whys, it's an exercise that you can also use it at work. When something fails, this is a useful exercise to kind of do the postmortem, why it failed, and to make sure that that failure doesn't happen again, so every framework is reusable in all sorts of contexts. Now we are moving to the second. I noticed that nobody wrote that they need the AI. Has anybody seen that? No? Hmm. Anyways, it doesn't mean that we don't use it, but it's just that it's not really a need at the moment. Fun facts of life. Okay. So the wall stays there, and at the end of the exercise, at the end of the workshop, you can all just maybe take a photo, screenshot, and analyze it. So we're moving on. And so the idea of this exercise is a little bit, this is my opinion now, that sometimes we are at, we think we want something, but that is not exactly what we need. And maybe here the question is, how often did it happen to you that you wanted something and after you got it, you weren't happy for long? It could be, of course, a new pair of jeans, a new bag, but, you know, for the shopaholics, but it can also be the last salary raise, you really fought for it, and at some point you fought for it so hard that by the time you got it, you were like, well, now I need another one. Anyway, and then the last promotion, and in the end, it just, I think, because we don't really, I mean, maybe like a quick question for the room, how many of you has ever gone to a therapist. Okay, there's quite a lot of you here, so that's actually good, because these are places and conversations where these conversations are happening to try to find out what is the need that you actually have, and because us as humans, we don't really reflect that much. There is not a lot of time to reflect at work. We have to move fast, break things fast, try AI, try cloud code and all that, and then at the end of the day, we realized that we actually wanted to do something else completely, but in the end we got pulled with the flow. So you can continue this five-wise exercise at home and go deeper in the other ones that you had and talk to yourself. And here may be a question that, like a reflection for you, a little bit of how did you feel when you got interrogated? At what point did you answer, when you started to answering, did it feel uncomfortable for you? Or you noticed when you were asking the other person that they were struggling to answer. And this is a sign that you need to do this more often. So do it as often as you want. Set yourself however habits tool. Of course, you can read the Atomic Habits book or the summary of it. Find your ways to get there. Okay, so the next exercise is called the Odyssey's Planning. It's from a book called Designing Your Life. And maybe a quick question, has anybody ever done this one? Okay, so this is not something that, it's a problem if you do it again, right? So you are fine if you do it again, because the more often you do it, the better it gets. It's not about planning and then stick it to the plan, it's just the activity of planning. So how do we do it? It's going to have like three stages. First, we are going to do the solo part, then the talking about it, and then the group debrief, which is going to be on that wall. So how it works, we will get paper in a second, but the idea is that you are imagining three possible futures that you can see in your life and thinking a little bit on how they feel. And what I would like to invite you today is to try to practice thinking about the possibilities and not focus so much on but how can I even get this done? You know, it's like don't think too much about what are the steps that you would have to do in order to do that. Because that's kind of a way how we stop ourselves from doing fun stuff sometimes. We kind of think oh, but I can never get this done. I can never do that. I don't even know how to get there, you know. This is a little bit of an exercise on, like, just what would you do? What would you want to do? And how would that look like? So we are going to do only two years. So this official exercise is about five years. But I don't know when is the last time that it made sense to plan your five years. So you see, this is not like a book written in the 1900s. It was written, like, maybe, like, some years ago. But it's already, like, five years. It's already too long. Okay. So think about your personal, both, so this is, again, not a place necessarily where you split the personal from career, so, you know, we cannot be like one person at work and one in our life, so it's together, and you can have different consideration, where will you live, maybe move, what will you be learning in that kind of life, what is your life going to look like, what role would you have, what feels scary or possible in that alternative, and what would you be happy about? So ask yourself these questions. You will have 15 minutes, and the three plans are, the first one is plan, I call it one, you can give it a name. If life goes on like it is now, what's going to happen in the next two years? It's just going with the flow. The second one is, what if what you do in this life number one is no longer possible? For example, you can get laid off, or something happens in your family, you have to move to another country. All sorts of things can just happen in your life that can happen. Or your job gets automated, of course. So what will you do if you can no longer live the current life? And the third one is you have all the money in the world. Isn't this amazing? You have all the money in the world. You don't actually care about your financial security or any kind of problems. what would that life look like in the next two years? So this is what I just said, but put here so nobody forgets anything. And if you don't have a piece of paper, grab a piece of paper and you make these three boxes maybe on three halves of paper or if you have more paper and you have 15 minutes, I will remind you when every five minutes is done so that you can move on to the next plan or time manage. So we are at 10.51, and this is going to run until 11.05, 11.06. If anybody needs more paper or pens. There's more. Yes. You're welcome. You're welcome. You can also do it in electronic format, of course. You're welcome. How's it going? Good night. you Thank you. you Thank you. Thank you. Thank you. So five minutes have passed. Ten more minutes. Thank you. Thank you. You're welcome. You're welcome. Thanks. You Thank you. Thank you Thank you. Thank you. Thank you. And five minutes left for the last plan, if you haven't started. And of course, if you're done, you can go grab yourself something to drink, coffee and be back in five minutes. No, I'll have water. Thanks. Thank you. Thank you. Thank you. I am. Thank you. Thank you. One minute. Go, go. Okay, so hopefully you're all set with the planning because now comes the part where you're going to pair up. You can decide whether you want to use the same pairs, conveniently wise, if you sit next to someone. So we're going to have another 10 to 15 minutes where you take time to share your reflection and tell the other person what your plans are. Walk them through the three plans. Take turns. And the person who listens, try to listen and then notice the energy the tone of the other person where do they hesitate where they're excited because you want to write on a piece of paper which you're going to fold what do you think the favorite plan of the other person is without asking them what's your favorite plan So it's going to be plan one, plan two, plan three, and at the end of this session's part, you just give the person the piece of paper folded with their plan, and we are going to use that in the next round. So take turns, one side listen so you have the time to split it up. I will let you know when we are at half time. Find a partner. And tell them about your three plans. And then take turns. Oh, yeah. Take, take. Thank you. Yeah, and it's also recorded. Thank you. Thank you. Thank you. Thank you. We are a bit at halftime. So everybody, we are a little bit at halftime. So be mindful that everybody gets a chance. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Just working all the time or just learning all the time. Thank you. Thank you. All right. Okay. So we are at the time. I hope everybody got to share everything. If you haven't written down what you think the favorite plan from how you heard it of the other person is, please write it down and give them the piece of paper with your opinion of what their favorite plan is. This is a fun exercise. I'm not sure if you've ever played that German old game. It's a board game called therapy. It's really cool. It's from the 80s or something. And you kind of have to guess what other people think. It's part of the game. Anyways, so do that because in the next step, you can take that piece of paper and you can walk to the wall there's three areas and then just walk to the place where your partner said you should go to you know it's like someone else deciding your life what else is new so the plan one is the yellow post-it the plan two is the pink one and so you don't need to do to put post-its there it's just walking there and then first take a moment to think whether you agree with the conclusion of your partner and after that, we can go all to the plan that you actually feel like you want. I haven't seen. No. But you can get another one, I'm sure. I think I lost it in this room. That's why maybe someone had found it. And if anybody found the badge, please bring it here. So, this is where you were told to go, and now maybe you can move to where you feel like So if you feel like you were read wrong, you can still take the moment to go to the spot where you feel like you actually... Okay. So this was the first exercise, was to go to where you were told to go. And now you can go to where you feel like, if you feel differently than how you got read. then you can change to where? Because I think this is a point you can talk to your, in the group where you are, maybe exchange a little bit like, what surprised you when you did all this planning today on the Odyssey planning? Is there something that you learned? And just find, look at the people that are on the same opinion as you are. And you can also be between plans. That is allowed, obviously. That is a valid state. Do you feel like you want to have, yeah? You don't know? That's a valid state. What did she think? She chose the first, okay. Okay. Did you? Yeah. What did she choose for you? She said to me I should do like new job or quit and heal and then nailed it on like oh your job is like going against your values. She thinks the same. She's told me many times. I mean in the end we're the only ones who are accountable to ourselves. also a timeline that feels like less scary yeah yeah i think also having a timeline it's like when i did the coaching at the start of the year that was the main thing for me like having a timeline and being like And, yeah, instead the pieces in motion. Yeah, maybe, but give yourself a deadline so you don't end up just staying because it's coming on and on. I mean, with my husband, I never gave myself a deadline, and just something happened that I needed to leave, and that was it. And it was like, you know, middle of the night, weekend, calling in my friends, help me pack, I need to, I need to leave. And it's like, yeah, well, I know I'm better for it, yeah, but it's, it's like not, like you don't, Thank you. You moved? You moved to plan A. Good, good. How is it? Did anybody move? No. It was a good experience to do it. Because I discovered that, yeah, Yeah, I don't have to push myself to the what-if. What if I have to work again or I have to... I would rather be more happy that I used the time where this was not the case. I agree. We have to... I think we are kind of super pressured into needing to have clarity like 20 years down the line But we just have to accept that maybe it's fine not to know what's going to happen Yeah, I think me, I have it a lot Because I plan, I do And at the same time it made me feel... It's fine if it happens But right now I want myself to be in where I am right now Good. Yeah, you're welcome. Thank you. Okay, so I'm going to break the part. So I will break the party for the last exercise. We do have one more exercise. It's a very short one. Very short. So I hope you all noticed the distribution. So a lot of people in one, more people in two, and many more in three. I wonder what this tells about things. So for the last exercise, it's a little bit about designing, like, thinking about future me. What do you need to do? Hi. Oh. We're, like... She's sick. Yeah. I'm just finishing the last exercise. You can stay for it. Yeah. I'm just finishing the last exercise. You can stay for it. It's an exercise. Okay. So for this last exercise, it's a little bit about behavior. So I think this is a take five minutes to think about now that you know kind of what life plan you would like to have. And think about what is something that your future version doesn't need to do anymore. Because you know, like, if you want to change something, you need to let some things go. Maybe what is the behavior that is stopping you from doing the thing you want? What is the behavior that if you continue doing, it doesn't actually work well with your future plan? So I'm here also tasks that take time. So think about for yourself what is something that if you would be on that new path that you said you want to do, what is something that you would definitely not do anymore? Whatever your desired life plan is, life setup, you're welcome. Thank you. Thank you. Thank you. Thank you. Thank you. And then, for the last, maybe, again, share with your partner what is a behaviour, you can say I noticed this behaviour, it makes sense to me that I'm doing it now, but, and Maybe the partner can ask you what are the consequences if you keep doing this, or why is it important that you change this now? And just have your last conversation with your new PyCon friend. But we're not going to do this for ten minutes. going to be like five, six minutes. And whoever is interviewing, you know, don't let the person and get away with, you know, half answers. Where are you going to be for lunch? Thank you. You're welcome. This is the, we are not done yet with the previous talk. Thank you. Thank you. Thank you. Thank you. Okay. I hope everybody got a chance to I mean, there's going to be lunch, coffee time outside so you can continue the conversation, obviously. Putting it all together for you for home, Maybe you can write it down for yourself, take like 30 seconds, not five minutes. So at the end of all this, you want to reflect on your wants and your needs and what is your favorite trajectory in life and a future behavior that ideally enables that and keeps you away from going into regressing, into behaviours, into ways of living that you have outgrown. And maybe ask for yourself what else can help you push towards this trajectory. Finding your allies, finding opportunities, saying yes to things that you normally don't say yes to things. And so on. And also a question for yourself is how would you implement this desired behaviour that you chose? So make a plan, you know, not just saying, oh, yeah, that would be nice if I continue to do things like this, but actually give yourself a little bit of a deadline and an action plan. If you want, you can take a picture of this and then when you're home or later, go through this and then ask yourself these questions. And I hope that you got a little bit of the reflection bug. You don't have to do it alone. You can always ask a friend to co-reflect. Reflecting on our own is usually sometimes hard for most of us. So that's the wrap-up and a little bit. Thank you very much for attending my workshop. I hope you learned a lot about yourselves. And this was an extract from the data diploma study group that I've run this year. And if you want to join the waiting list for the next iteration, I usually do very small groups of people for this. You can check the QR code. And, of course, you can connect with me on whatever platform you want to connect with me. You will find me. And, yeah, wish you all a wonderful conference and he has if there are any questions Currently there are no questions submitted to talks.pycon.de Are there any questions left open in the room? Thank you so much that was a brilliant session I got lots of questions but one was about how you stay grounded in a world that doesn't really give you conditions for doing that very easily except for it seems very elite tech bros who seem totally fine how do you kind of find you know your community in this strange world that we're in I think the word that you said there is correct seem fine I think a lot of us are great at pretending to be fine. So including the tech pros, I'm pretty sure that they have issues. Everybody has issues. So I think on one side we have PyLadies communities and there's local communities, online communities, and also trying to connect at events like this with people on another level than on the technical level there is also a space for that and yeah look for opportunities to find a space to that enables this like you came to this workshop there's I think in the afternoon another session on several sessions on career and and in the end And it's a little bit, I think, again, coming to self-reflection to kind of notice, like, when you're doing things on autopilot and try to, I mean, even Cloud and all of these tools, they have planning mode and autopilot mode. So we should apply to ourselves a little bit that we first kind of are intentional about what we want to do versus just do things all the time and going in autopilot mode. Otherwise, we use all our tokens. Oh, my gosh. I think we have time for one more question. Thank you for the workshop. It was a really fun experience. I'm curious about the name Data Diplomat for the study group. I don't know. How do you use data there? and yeah, the diplomats. I think, yeah, thank you, Sara, for the question. So yeah, so I think my study group, because I usually try to work with people that are in close to leadership roles that are around leadership, but also working in data topics. And I think it's a little bit, I think this kind of came up to me like several years ago that the most important skill when you work in data departments is diplomacy, because you have to interact with stakeholders from so many other levels, disciplines. And if you do this intentionally, you can get quite far in your career or you might make mistakes and also learn, but maybe it's not as quick. So a little bit, that's the diplomacy part and the data. It's time to wrap up. If you have any more questions, please approach Teresa after her workshop. But thank you again, Theresa, for your wonderful workshop. A big round of applause, please. And thank you, all of you. I hope you take stock about what an incredible effort is to spend an hour and a half in self-reflection and be proud of yourself for that.

Tereza Iofciu

Tereza Iofciu is a data and AI expert, leadership coach, and PSF Fellow with 15+ years of experience leading data and product teams at neuefische, FREE NOW, and New Work (XING). She helps professionals lead and adapt in the age of AI through her Data Diplomat Framework™, bridging technical depth with human leadership.

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