Big Sis Briefing: Did we train for a career that doesn’t exist anymore?

I've been thinking a lot lately about something I keep hearing from mid-to-senior lawyers. This feeling that somewhere along the way, our career path stopped making sense.

We did everything right. Got the degree, joined the firm, worked the hours, made senior associate or general counsel or maybe partner. Followed the path exactly as it was laid out. Now, we're 10, 15, maybe even 20 years in and wondering: is this it? Is this what I was working toward?

I've been there too.

I'm hearing it more from other people.

I think something bigger is going on here.

When the golden path stops feeling like progress

We trained for a version of a legal career that looked a certain way. Clear progression. Stability. Respect. The promise that if you worked hard and followed the rules, things would eventually settle into something sustainable and meaningful.

For some people, that's still how it works.

But I keep hearing from lawyers who are realising it doesn't feel the way they expected.

The prestige feels thinner than it should. The partnership carrot they dangle keeps moving further away, or you have ‘made it’ and realised it wasn't the arrival you thought it would be. The work-life balance you were promised never materialised. The leaders above you don't seem much happier - they seem more tired, more trapped even.

Then there are the bigger disappointments. The institutions we respected have let us down in very public ways. Royal commissions exposing things that were always there, lurking in the dark. COVID showing us how quickly we could become expendable. Leaders we once looked up to protecting systems that caused real harm.

I think a lot of us are realising we trained for a career model that was built for a different world, one where loyalty went both ways. Where putting your head down in your 20s and early 30s genuinely paid off later. Where the destination was worth the journey.

For many, the loyalty hasn't always been mutual.

The payoff keeps getting deferred and in the meantime, we're starting to question whether we even want what we were working toward all this time (ooft).

Meanwhile, we're watching other people make different choices. Younger lawyers turning down opportunities we would have competed for once upon a time. Colleagues leaving to build fractional practices or consultancies that offer actual flexibility. People sharing how much better their lives and nervous systems are since they stepped off the “traditional track”.

We're still here, wondering if there's something we're missing. Wondering if there might be a different way. Wondering if it's too late?

But why does it feel so hard to leave?

I've been trying to understand why this transition feels so difficult for those of us at this stage. If we put aside the golden handcuffs, I think it comes down to a skills gap that no one really talks about.

We have deep legal expertise. We have years of experience and credibility in our existing networks. But most of us don't have the skills we'd need to build something different (yet).

We don't necessarily know how to structure work that isn't billed by the hour. We don't know how to find clients outside the referral networks we already have. We don't know how to talk about what we do in ways that resonate with people who don't know us yet. We don't know how to build the kind of visibility that brings opportunities to us.

These aren't small gaps. They're real business and marketing skills that take time to develop. The thought of learning them feels overwhelming when you’re already stretched thin.

So, you stay.

Not because you love where we are but because building the alternative feels impossibly hard from where you're standing.

I'm learning all of this myself, in real time. The skills I need now - finding clients without a business development team, managing my own revenue and expenses, building systems and processes that used to just exist around me - none of that was covered in law school or legal practice. I'm figuring it out as I go, often feeling like I'm back at square one with things that seem like they should be straightforward.

A bigger shift?

I think we're in the middle of a generational transition in how legal careers work.

Those of us who are Millennials or older Gen X grew up with a particular story about professional success. You got the degree, put in the years, climbed the ladder and eventually things would stabilise into something good. That story made sense when we started and so, a lot of us built our entire lives around it.

But that story has been breaking down. Institutions have failed publicly and dramatically. The security we were promised turned out to be conditional and tenuous. The respect we were working toward feels a little hollow. The leaders who were supposed to model the destination don't seem to be enjoying the view all that much.

Younger lawyers are watching this and making different calculations. They're not waiting 15 years to realise something's broken. They're setting harder boundaries earlier. They're building backup plans and side projects, even cosplaying corporate life as part of a bigger content strategy. They're walking away from prestige when the cost is too high - the ROI isn’t stacking up for them.

I don't think the traditional path is disappearing completely. But I do think it's losing some of its pull and those of us in the middle - who invested heavily in a model that made sense at the time - are trying to figure out what comes next.

What different might actually look like

I've been watching people build alternative legal careers and trying to understand what actually makes them work.

Some people are doing fractional GC work across multiple clients. Some are building consultancies. Some are coaching other lawyers through transitions. Some are creating content or resources or courses. Some are mixing legal work with adjacent skills in ways that feel more sustainable for them.

What they all seem to need are skills most of us weren't taught. Business fundamentals - how to structure offers, price expertise that isn't hourly and manage revenue without a firm's infrastructure. How to build relationships and find clients outside existing networks. How to communicate expertise in ways that land with people who don't already know you. How to create visibility through writing or speaking or sharing knowledge so opportunities can find you.

They all seem to need comfort with not being expert-level at everything anymore. They know that you can be great at law and still be learning how to run a business or create content. That discomfort is just part of the process.

They also need time and space to figure things out. Which is genuinely hard to carve out when you're managing a full workload and a life outside work.

I'm not going to pretend this is easy. It's not. It's why most people don't make the jump. Not because it's impossible but because it's genuinely demanding and the path isn't clear.

Some thoughts to sit with

If you're reading this and feeling exhausted or stuck or uncertain about how much longer you can keep going like this - I get it. The career we trained for is shifting shape and it's disorienting. Maybe even just hearing that from a colleague from the same vintage is enough?

Also, you don't have to leave. The traditional path still works for some people and if it's working for you, that's completely valid and wonderful. But if it's not - if you're starting to feel like there should be another way to practice law that doesn't require this much of you - it might help to know that other options are emerging.

They're not necessarily easier options. They require learning new skills, tolerating uncertainty, building something without a clear template. But people are doing it. People at our stage of career, with our level of experience and similar constraints.

The lawyers making this work aren't necessarily smarter or braver. They just started learning these skills a bit earlier, had circumstances that made the risk more manageable or reached a point where staying felt harder than leaving (guilty!).

I'm figuring this out myself and am only 6 months into my post-corporate life. Learning business skills from those that have gone before me and learning how to position myself in a market that doesn't have a clear category for what I'm building. It's messy and uncomfortable and often feels like I'm making it up as I go (I am). It’s entirely humbling.

But I'm also starting to see how these skills create options. Real options that don't require someone else's permission or infrastructure and are more future proof.

For now, maybe it's enough to notice what you're feeling. The sense that something's off. That the path you're on doesn't quite lead where you want to go. That there might be another way, even if you can't quite see it yet.

You're not imagining it. You're not failing. You're just noticing that the world has shifted and the career model we invested in might not fit the lives we actually want now.

It’s not a crisis, it's just new information. What you do with that information is entirely up to you.

Onwards!

Mel

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