Navigating the Millennial Success Trap [TFLP256]

Millennials are often described as the generation caught between two worlds. On one side, we’re influenced by the economic expectations of our parents’ generation. On the other, we’re grappling with systemic economic challenges that have fundamentally reshaped what success looks like.

For lawyers, these pressures are amplified. The high stakes and rigid paths of the legal profession make it hard to imagine stepping away, even when the work is draining and unsustainable. On this episode of The Former Lawyer Podcast, I unpack the “success trap” many Millennials experience and how you can navigate your way out of it.

Why Success Feels Like a Trap

One of the hallmarks of the Millennial experience is feeling stuck in the pursuit of an unattainable ideal of success. Many lawyers stay in toxic work environments because they believe they need to maintain a certain salary or lifestyle to meet societal or familial expectations.

This “trap” often stems from deeply rooted beliefs about what success should look like—ideas handed down by family, culture, or the legal profession itself. Even when those beliefs don’t align with your values or well-being, they can be hard to shake.

Rethinking Success on Your Terms

Breaking free from the success trap starts with self-reflection. Ask yourself:

  • Do I feel pressure to maintain a certain lifestyle or salary?
  • Why do I believe this is necessary?
  • Does this align with my current values and priorities?

Often, these pressures are more about perception than reality. Therapy can be an invaluable tool to help you unpack these beliefs and realign your life with what truly matters.

The Role of Therapy in Breaking the Cycle

Many lawyers I’ve worked with discover they’ve internalized the idea that suffering is a prerequisite for success. This mindset often leads to burnout and disillusionment.

Therapy helps untangle these narratives and introduces a new way of thinking: valuing your well-being as much as your achievements. By addressing the systemic and personal factors that contribute to the success trap, you can start making choices that reflect your true priorities.

Moving Forward

You don’t have to stay stuck in the success trap. Recognizing that your worth isn’t tied to external markers like salary or job title is the first step. From there, you can redefine success in a way that supports your mental and emotional health.

If this resonates with you, take the next step by downloading my free guide, First Steps to Leaving the Law.

Let’s explore what’s possible when you break free from the success trap and build a life that aligns with your values.

Hi, and welcome to The Former Lawyer Podcast. I'm your host, Sarah Cottrell. I practiced law for 10 years and now I help unhappy lawyers ditch their soul-sucking jobs. On this show, I share advice and strategies for aspiring former lawyers, and interviews with former lawyers who have left the law behind to find careers and lives that they love.

Today's topic is maybe a little controversial, but I have a lot of caveats, so listen to everything before you think, "Wow, Sarah, you've really gone around the bend." This is something that has come up frequently, especially with my clients who are my generation and younger.

I am an elder Millennial, also known as a Xennial, born in that micro-generation between '77 and '84. One of the hallmarks of the Millennial experience for many people—and there are all sorts of data out there—is about how Millennials are the first generation who are economically struggling in all these different ways more than previous generations.

I was reading another article about this or probably some meme on Instagram Reels like the 41-year-old that I am and it made me think about several conversations that I had had in the past couple of weeks with clients and with some members in the Collab about the challenge that people run into feeling like they need to maintain a certain standard of living.

They need to stay in their law job and maintain a certain standard of living, not necessarily even because they objectively feel the need to maintain that exact particular standard in every respect, but because they have this very deep-seated sense that they are supposed to have at least as much, but ideally, more than their parents had economically, etc.

I think there are so many complex questions that go into the way people think about this, so many things related to your family of origin, what was expected, how lifestyle and economics were presented and talked about, and all of these sorts of things. But fundamentally, there is this sense of even if I was willing to take a step back economically or career-wise, it feels wrong because it feels like I need to maintain a certain earning power and earning potential, and also that I need to maintain a certain lifestyle or way of existing in the world that reflects or is equal or greater to what I saw in my upbringing.

To be clear, I'm not saying, “That's just ridiculous. Why would anyone ever think--” because first of all, hello, we're human and that is actually quite normal, also, I think there are lots of reasons that people feel pressure to maintain a certain economic status, and many of those things are intrinsically tied to a sense of security and safety, which security and safety and its relationship to money and economics is something that comes up so, so, so often in career coaching when you're talking about changing careers or even when a lawyer is thinking about potentially changing careers in all sorts of different directions.

I don't necessarily mean only, “Oh, you're always contemplating a pay cut,” because that isn't true, but it's just the economics of it all are fundamentally bound up in the decision. I'm not here to tell you, “Who cares? It doesn't matter, throw any of your preferences around your economic situation in the trash because it's not as important as anything else.”

No, I'm not saying that. But it struck me as I was having these conversations and being a Millennial myself and obviously having many, many, many friends who are Millennials and younger. I think it is really worthwhile to think about whether or not this particular set of beliefs is operating for you.

By which I mean, I think it is really important to ask yourself, “Do I feel pressure to maintain a certain lifestyle, to maintain a certain salary, to maintain a certain whatever [fill in the blank]? Why is that? Do I want that to be the case? If not, what do I need to shift?”

Of course, this is when I bring up therapy and tell you yet again that if you're a lawyer who's thinking about making a career change, I truly cannot recommend therapy enough because it does touch on a lot of these fundamental questions.

But I think it really is important, even just to notice like, “Oh, what do I believe about how successful I should be?” Successful in whatever way you define success. Even what do I think success is? Success in life, success in business/my career. Where do those ideas come from? Are those ideas consistent with my values as of today?

If they are, how can I lean into them more? If they're not, what do I potentially want to shift? Because I have found that it is true that some people recognize that they've created an artificial trap for themselves, or they have set up this idea of what they're supposed to be doing and what expectations they should be meeting.

Those aren't necessarily shared by even the people who think that they derived those from like their parents. Even if they have a completely accurate perception and their parents or their family really do have a certain sense of what their life should look like, there are still some really complex questions to think about around those things, among other things for someone, of course, there are many people for whom this is the case, for someone whose mental and physical health is being negatively impacted by the lawyering experience, I think there needs to at least be a consideration of, okay, there are actually competing interests here.

There are competing ideals, there are competing values in the sense that I have the sense that my life needs to look a certain way, my achievements need to look a certain way, my career needs to look a certain way, but also it is causing me extreme distress. I talked about this a couple of weeks ago on another episode, but I think one of the things that is really important for lawyers to learn to do—because many lawyers did not learn to do this in their upbringing—is to value their own distress.

In other words, to say, “It matters that this is causing me this level of distress. How do I balance the reality that I do feel that certain things are necessary in terms of what I'm supposed to be pursuing in terms of lifestyle, career, etc., and the fact that I am a human person who deserves not to suffer?”

Side note, if you do go talk to a therapist, I have found that many, many, many people who have become lawyers also believe that there is some element of like they should suffer in order to achieve and therefore that's part of why it is so hard to even see their own suffering as something that merits some sort of consideration. Just stick that in your back pocket and take it off to your therapist if that resonates. If it doesn't, just let it go.

Okay, in conclusion, such as it is, if you're a millennial or younger and you find yourself trapped in this headspace of, “I need to be certain things because of some external marker like my past history or experience or expectations or whatever,” again, I'm not saying, “Throw it all in the trash. Who cares?” But I do think it is really worthwhile to think through like, “Okay, why do I think that? Is that consistent with my values? Are there ways that I might want to make a shift and what would that look like?”

Also just recognizing that we're talking about very broad systemic economic trends here. I think every lawyer feels like they should be the exception to the rule, it's like the mind over a matter thing. But the reality is that you are, among other things, a product of your time and your generation.

If you find yourself feeling trapped in a scenario where you are struggling to meet what feels like the expectations of what your economic life should look like because it doesn't look like what your parents look for example, that isn't a personal moral failing.

I’m laughing a little because the vast majority of lawyers, if they aren't doing something that they think they should be doing, almost always assume it's because they're failing in some way, they've done something wrong. The reality of much of this is far broader than any one individual, like these economic trends we're talking about.

That's just some food for thought for the millennials and younger out there and really for all generations in terms of examining your thinking about what whatever stage of life you are in should look like. Because again, so many of these ideas that we have were given to us and we assume that they're right and often it's not a question of whether they're right or wrong, it's just a question of, “Is this actually consistent with what I value and what I want my life to look like?”

This is a great conversation to have with a therapist. If you're ever looking for a therapist, I'm sure I've mentioned this in the podcast before, but Psychology Today has a great search database where you can look for therapists based on all sorts of specialties and their location and kinds of insurance they take and blah, blah, blah.

Definitely check out that database if you are looking for a therapist or listen to one of the many episodes of the podcast where we've had therapists, and former lawyers turned therapists on to get a sense of what type of therapy or therapist might be a good fit for you. Thanks so much for listening. Have a great week.

Thanks so much for listening. I absolutely love getting to share this podcast with you. If you haven't yet, I invite you to download my free guide: First Steps to Leaving the Law at formerlawyer.com/first. Until next time, have a great week.