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Career Growth Roadmap - De-risking Your Career By Understanding Your Vulnerabilities

Summary

This episode introduces a framework for understanding how various aspects of your life exert power over your career decisions. The host explains that everyone has a list of things—whether financial obligations like credit card debt, personal relationships, health concerns, or professional aspirations—that can significantly influence career choices, sometimes limiting options or creating vulnerability.

The exercise involves identifying these sources of power in your life and assessing which ones you want to maintain (like meaningful relationships where vulnerability is part of the connection) versus which ones you want to reduce or eliminate (like financial burdens that unnecessarily constrain your career mobility). The host emphasizes that these vulnerabilities aren’t necessarily bad—they often align with what you value—but they do have leverage over your decision-making process.

De-risking involves strategically reducing these vulnerabilities to gain more autonomy. For example, paying off credit card debt removes a financial constraint that might prevent someone from taking a more fulfilling but lower-paying job. The process requires shifting control—giving up certain comforts or spending habits in the short term to gain long-term career freedom. This creates a virtuous cycle where reduced vulnerability leads to clearer perspective, better alignment with personal values, and more purposeful career decisions.

Ultimately, the goal is to create enough agency in your life that you can make career decisions based on principle and alignment with your values rather than being forced by external pressures. This approach not only reduces career risk but also enables more meaningful professional growth and satisfaction.

Topic Timeline

  • 00:00:00 — Introduction to career de-risking — Jonathan introduces the episode’s focus on de-risking your career by understanding vulnerabilities. He explains that reducing risk often aligns with career growth and sets up an exercise for listeners to identify what influences their decision-making.
  • 00:01:26 — Identifying sources of power in your life — The host guides listeners to think about what drives their decisions—money, relationships, health, debt, etc. These are things that have ‘power’ over decision-making. Some are positive (like valued relationships) while others create vulnerability (like debt). The key is recognizing which vulnerabilities you want to maintain and which you want to reduce.
  • 00:05:44 — The de-risking process explained — Jonathan explains that de-risking involves gaining agency over decision-making so vulnerabilities have less leverage. This is essentially a ‘pre-mortem of career failure’—anticipating what could go wrong and proactively addressing it. The goal is to understand what has power over you so you can make career decisions with more autonomy.
  • 00:07:54 — Credit card debt example — Using credit card debt as a concrete example, the host shows how financial obligations can limit career choices. Someone with significant debt may feel unable to take a lower-paying job they’d prefer. Paying off the debt removes this constraint, allowing more career freedom. This illustrates how de-risking one area (finances) creates opportunity in another (career options).
  • 00:11:41 — Shifting control for more autonomy — The discussion turns to how de-risking involves shifting control—giving up certain comforts or behaviors to gain autonomy elsewhere. For instance, changing spending habits to pay off debt means less purchasing power now but more career freedom later. This control redistribution helps reduce feelings of constraint in decision-making.
  • 00:13:29 — Benefits of reduced vulnerability — Jonathan explains how reducing vulnerabilities leads to clearer perspective, better alignment with personal values, and more principled career decisions. With fewer external pressures clouding judgment, you can make choices that truly align with your purpose rather than reacting to immediate pressures or fears.

Episode Info

  • Podcast: Developer Tea
  • Author: Jonathan Cutrell
  • Category: Technology Business Careers Society & Culture
  • Published: 2026-01-20T13:00:00Z
  • Duration: 00:15:19

References

Podcast Info

Transcript

[00:00:00] hey everyone and welcome to today’s episode of developer t my name is jonathan cuttrell

[00:00:04] and my goal on the show is to help driven developers like you find clarity perspective

[00:00:07] and purpose in their careers and in today’s episode i want to talk about ways of de-risking

[00:00:14] your career on your career growth roadmap and interestingly the flip side of de-risking

[00:00:21] also tends to align with career growth we’re going to talk a little bit about how that works

[00:00:27] the first thing i want you to do if you’re listening to this episode is to either pause it

[00:00:34] or you know take take a minute after the episode to run through this exercise it’s not very

[00:00:40] complicated the exercise is very simple i want you to think about the things in your life the

[00:00:49] people uh you know maybe the situations maybe the the literal physical things

[00:00:57] that drive your decision making right so for most people of course one of the things on this list is

[00:01:03] money but it usually shows them shows up in different ways specifically how would you use

[00:01:10] the money that you make how do you currently use it you can look back and see how you have

[00:01:17] made decisions around money what kinds of things are on this list but secondly i want you to think

[00:01:26] about what kinds of things are on this list and what kinds of things are on this list

[00:01:27] what kinds of things would change your decisions

[00:01:31] what situation could occur that would shift your decision making that would shift your behavior

[00:01:39] that would change how you spend your time maybe it would change how you spend your money uh and

[00:01:47] you develop this list of of things that are uh are very powerful and have a lot of uh um kind of

[00:01:57] value over your decision making this list is very important for you to be aware of because while

[00:02:05] this list is ultimately probably fairly well aligned with things that you value there are also

[00:02:13] things on this list that could hold you hostage right now i don’t necessarily mean in a hostile way

[00:02:22] um more what i mean is

[00:02:25] that you could end up

[00:02:26] making decisions that you otherwise would not have made, had it not been for some aspect,

[00:02:34] something on this list that kind of pushed you that direction. So basic examples of this might

[00:02:39] be large amounts of debt, right? You know, the kind of the positive versions of this might be

[00:02:46] relationships that you care deeply about, whether that’s family or friends, or whatever is on that,

[00:02:52] you know, on that vertical for you as well. Your personal health, you know, at some point,

[00:02:59] your personal health, you wouldn’t have a choice, right? But to be held, you know, essentially

[00:03:04] hostage. But you could also look at maximizing your personal health. Maybe that’s something that

[00:03:10] you value very, very much. And so that’s not necessarily a bad thing to have on this list.

[00:03:18] But the important thing that you need to recognize here is that

[00:03:21] when we care very deeply about something, or, you know, when we care, you know, about not losing

[00:03:29] something, right? Like, for example, if you didn’t pay your debts, you may, your credit score may

[00:03:36] drop, you may lose out on future potential of owning things, you may have something repossessed,

[00:03:41] your car, your home. These are all nightmare scenarios that are probably for most people on

[00:03:46] this show, or listening to the show, rather, it’s unlikely for you, right?

[00:03:51] But they’re not things that could never happen. In other words, that was kind of a double negative,

[00:03:59] wasn’t it? So it’s these, these are situations that could, theoretically, if you didn’t pay

[00:04:05] your bills, you could lose your home, you could lose your car. So what this list highlights for

[00:04:14] you are things that are powerful in your life.

[00:04:21] To you.

[00:04:23] And as a general rule, these are the things that you’re going to make most of your large decisions

[00:04:30] around.

[00:04:32] Whether that’s managing your debt, maybe it’s aligning your time so that you can spend it with

[00:04:38] friends, maybe on this list is something as as simple or as critical as the domain that you want

[00:04:46] to work and you care very much about working in some kind of domain. And so

[00:04:50] If your organization, let’s say you join a company and you find out that they’re moving

[00:04:58] away from a particular domain, that may have enough leverage over you that you decide that

[00:05:02] you’re going to leave that job, right?

[00:05:05] So what you want to understand here is that this list, the power that these things have,

[00:05:11] the values kind of cut both ways.

[00:05:14] And so it makes sense to de-risk yourself in as many of these areas as possible.

[00:05:22] How can you gain enough agency over your own decision-making so that these areas have less

[00:05:31] leverage, right?

[00:05:33] What would have to be true, for example, for you to not go, you know, into the red on your

[00:05:41] mortgage?

[00:05:42] And this is the basic de-risk.

[00:05:44] The de-risking process, right?

[00:05:45] You’re, you know, everybody makes different decisions with their money.

[00:05:48] Everybody makes different decisions with their time, with their careers.

[00:05:52] And what we’re really trying to do is kick off kind of a pre-mortem of career failure.

[00:06:01] That’s really what this exercise is.

[00:06:03] But it starts with trying to recognize the sources of power in your life.

[00:06:09] When I say sources of power, I don’t mean anything mystical or magical or new.

[00:06:14] I mean, very simply, the things that would have the power to change your decisions.

[00:06:22] Situational, relational, whatever it is.

[00:06:25] These are things that have power over your decisions.

[00:06:28] And so these matter because in order for you to gain as much autonomy as possible,

[00:06:33] in order to make decisions about your career that you want to make,

[00:06:38] you need to have a clear awareness of the things that have power over you.

[00:06:44] Right?

[00:06:45] And identify the ones that you are, you accept, right?

[00:06:48] So for example, you know, in some of those relationships,

[00:06:52] part of what keeps the relationship in a positive place, right?

[00:06:57] Part of kind of the definition of that relationship is vulnerability.

[00:07:01] And so you’re vulnerable because that person has some power over you

[00:07:05] to change your decision-making, right?

[00:07:08] If I de-risked my, you know, reliance on my relationship,

[00:07:14] with my wife or my children,

[00:07:15] that would probably create some distance

[00:07:19] because it would eliminate some of the vulnerability that we have with each other.

[00:07:23] And that’s not something that I want to elect to do.

[00:07:26] But I don’t need to be vulnerable with my creditor, right?

[00:07:30] I don’t really want to have that vulnerability.

[00:07:33] In fact, as soon as I can close out that relationship,

[00:07:36] that’s what I want to do.

[00:07:38] So, you know, ways of de-risking those situations,

[00:07:42] create more autonomy.

[00:07:44] And create more opportunity for me to make decisions in my career

[00:07:50] that may otherwise feel too risky, right?

[00:07:54] I may go and join a company.

[00:07:56] This is how this ultimately ends up playing out, right?

[00:07:59] So let’s take credit card debt, for example, okay?

[00:08:04] I could either choose to continue on with credit card debt,

[00:08:09] hanging over my head,

[00:08:10] and build that bill up,

[00:08:12] increase my debt,

[00:08:14] and ultimately, I’m beholden to paying that debt off.

[00:08:18] And so therefore, you know, I need to have a job that allows me

[00:08:21] that I have enough income to pay that debt off.

[00:08:23] Okay, so that’s the basic calculus, right?

[00:08:27] And so with that debt, I’m unlikely to take a pay cut

[00:08:31] to go and work for a company that I may really want to work for,

[00:08:36] but they just can’t quite pay me enough to deal with this other vulnerability.

[00:08:43] And so,

[00:08:43] my credit card debt has power over my decision-making about where I work, right?

[00:08:49] So, and this can even be, you know, jobs that pay decently well.

[00:08:55] So, and that’s a very common example, right?

[00:08:58] So instead, what can I do in order to improve my autonomy

[00:09:04] and ultimately give me more agency in my career

[00:09:08] and potentially allow me to take more risks in my life?

[00:09:13] I allow myself to take more risks in my life.

[00:09:13] I eliminate other risks.

[00:09:15] So I may buckle down, you know, save what I need to save

[00:09:18] in the higher paying job in order to pay the credit card off entirely.

[00:09:22] And now that vulnerability is reduced in my life.

[00:09:26] You know, money isn’t always the answer.

[00:09:28] Sometimes it’s as simple as, you know, trying to square with

[00:09:33] the risk of not paying that debt off.

[00:09:38] You know, how can I, what happens in my life?

[00:09:41] And am I okay with that?

[00:09:43] You know, very similarly, we may need to, you know,

[00:09:47] do some introspection and figure out how we can relate differently to our, to our jobs.

[00:09:52] Some of the parts of our job that we previously may have called non-negotiables.

[00:09:57] Now we adjust our, you know, we do again that introspective work to figure out,

[00:10:02] okay, what is actually important to me here?

[00:10:05] You know, what are the real risks that I’m trying to mitigate, for example,

[00:10:09] versus the ones that I’m imagining?

[00:10:12] Am I creating?

[00:10:13] Am I creating a problem where there doesn’t need to be one?

[00:10:16] And so if that’s the case, then I might be, you know, less likely to leave a job, right?

[00:10:22] Less likely to leave a company just because of some small failure or some small misalignment.

[00:10:30] Maybe the leadership at the company, I don’t have perfect alignment with their personal values.

[00:10:35] Can I relate to that situation differently so that I’m not constantly seeking

[00:10:42] a company that I’m not constantly seeking?

[00:10:43] Maybe the leadership at the company, I don’t have perfect alignment with their personal values.

[00:10:43] Maybe the leadership at the company, I don’t have perfect alignment with their personal values.

[00:10:43] Where everybody in the company has exactly the same values that I have,

[00:10:47] exactly the same belief system that I have.

[00:10:50] If I can find a way to relate to that differently, then I’m de-risking that, right?

[00:10:55] I’m taking some power out of that, some power that it otherwise would have had over me.

[00:11:01] I’m kind of reclaiming that, right?

[00:11:04] And now I have a little bit more agency to make my own decisions about those situations.

[00:11:11] So really what you’re doing here is you’re trying to,

[00:11:13] you’re trying to figure out, okay, what are the things that would change the way I make decisions?

[00:11:18] And, you know, do I want to keep that vulnerable relationship?

[00:11:23] Do I really want to be beholden to that particular value set?

[00:11:28] You know, do I want that thing to have that power over me or do I want to shift it?

[00:11:32] And if so, what way would I like to shift it?

[00:11:35] How should I change my relationship to that thing so that I have more agency autonomy?

[00:11:41] What this ultimately,

[00:11:43] what it tends to look like and why it usually leads to growth.

[00:11:49] This usually means that we’re trying to take control of certain aspects of our life in a different way.

[00:11:59] So we give up control in one area and we take control in another area, right?

[00:12:05] So in the example of the credit card debt, instead of,

[00:12:12] you know,

[00:12:13] continuing on having debt,

[00:12:14] then I’m going to take control of my current finances so that I can pay that debt off.

[00:12:20] You know,

[00:12:20] I’m going to try to change my spending habits for some amount of time.

[00:12:24] I’m adding control in one area and I’m potentially releasing control in another area.

[00:12:32] So in that example,

[00:12:34] you know,

[00:12:34] you might be releasing control over the things that you were able to buy with the credit card.

[00:12:43] All right.

[00:12:44] So no longer are you going to have,

[00:12:47] you know,

[00:12:47] that much purchasing power.

[00:12:49] Maybe that behavior has to change.

[00:12:51] And so you’re,

[00:12:52] it’s a control system and you only have so much of that agency.

[00:12:57] But if you route it to the correct things,

[00:12:59] then you can de-risk your situation.

[00:13:01] So you’re less likely to feel constrained in your decision making.

[00:13:08] And as a general rule,

[00:13:09] that doesn’t necessarily mean that you’re going to feel totally free to make any decision.

[00:13:14] It also doesn’t mean that you’re going to end up in a financially better off position.

[00:13:19] All this really means is that you have more autonomy over your decision making without violating any of your relational vulnerabilities.

[00:13:29] Right.

[00:13:31] And so with that autonomy,

[00:13:34] you may be able to make a more kind of principled decision that aligns with your personal values,

[00:13:41] your clarity,

[00:13:42] perspective and purpose.

[00:13:44] You’re able to get a little bit clearer,

[00:13:46] right,

[00:13:47] on what you care about and how you want to operate about what you care about.

[00:13:53] You’re able to have certainly,

[00:13:54] this is the biggest one,

[00:13:56] a different perspective.

[00:13:57] Right.

[00:13:59] If you have a bunch of things that are clouding your decision making that you feel like you have to respect or that are that are kind of influencing your decision making and your perspective is probably lacking.

[00:14:14] Right.

[00:14:14] And finally,

[00:14:16] because of that,

[00:14:17] because of these,

[00:14:18] this change in your clarity and perspective,

[00:14:22] you’re able to more directly align with what you hopefully have identified as a purpose driven approach to your career.

[00:14:33] Thank you so much for listening to today’s episode of Developer Tea.

[00:14:35] It’s kind of a different discussion about values,

[00:14:39] really looking at how you,

[00:14:42] you know,

[00:14:43] what level of freedom do you have based on how your values shift your,

[00:14:48] you know,

[00:14:49] not just your values,

[00:14:50] but how different kind of responsibilities or burdens,

[00:14:55] how they change your decision making.

[00:14:56] So hopefully this gives you some idea and I hope this exercise gives you some value yourself.

[00:15:03] If you enjoy this discussion,

[00:15:05] please subscribe and whatever podcasting app you’re listening to.

[00:15:08] Of course,

[00:15:08] this is also on YouTube.

[00:15:09] Now we’re continuing to invest in the quality of our YouTube.

[00:15:13] So you can expect that to get better and better.

[00:15:15] Thank you so much for listening and until next time,

[00:15:17] enjoy your tea.

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