The messy middle of careers
Why you may feel lost between when you are in between 5 and 15 years of experience, and what to do about it
Hey, we are Ramón Rodrigáñez and Andrea Marino, Co-Founders at Nova, the Global Top Talent Network.
Welcome to Talent First, our newsletter where those who believe that talent is the most important resource in the economy get together.
Every week, we cover a new topic related to attracting, hiring, developing, and retaining talent, as well as the learnings from our journey building Nova.
Summary
Why the “I don’t know what to do with my career” moment hits harder in mid-career: understanding the difference between early-career confusion and mid-career crisis.
The generational shift in career expectations: how Millennial and Gen-Z workers are navigating a more fluid, uncertain work landscape, which is simply more challenging.
5 pieces of advice if you’re in the Messy Middle: practical, reassuring steps to gain clarity and momentum.
Stories from Novas and lessons from our journey: real voices from the Nova community showing what the messy middle really looks like and what can inspire you to move forward if you face similar doubts.
1. The same question, 2 very different reasons
1.1 “I don’t know what to do with my career” version 1: Early Career
When we hear this phrase from Novas who are just entering the job market, we nod in understanding.
It’s perfectly normal. After all, how could you know what you want to do before even doing it?
We expect uncertainty at this stage. You're supposed to explore. That’s the whole point of internships, entry-level roles, bootcamps, rotational programs, and awkward coffee chats where you ask, “So… what do you actually do all day?”
This is not a problem to solve: it’s where almost everyone in history has been and will always be.
The latest data we have is that +50% of jobs that will exist in 2030 do not exist today or do not exist in the same way - so it’s silly to worry.
Having said that, you have to work on your career as soon as possible. The sooner you start doing internship, getting exposure, and trying things, the more chances you will land a great job that actually suits you.
The importance of “signaling” (i.e. getting logos and experiences in your CV that signal your potential) cannot be undermined, no matter how you measure your career “success” (salary, development, impact, etc.).
Thus, pick a company where you'll grow fast, choose leaders you can learn from and try to get great logos on your resume. And do not be too worried if you missed your first or second chances, but make sure to be right as soon as possible.
It’s like dating: figure out what energizes you, what bores you, and what red flags to avoid.
At Nova, we have the Bright Future Program to support you and help you explore careers as you are about to join the labor market.
1.2 “I don’t know what to do with my career” version 2: The Messy Middle
But then, this same phrase resurfaces… about ten years later.
And this time, it feels different.
You’re not a beginner anymore. You’ve had 5, 8, 12, maybe even 15 years of experience. You’re not lost because you’ve never done anything: you’re lost because you’ve done so much, and you’re still unsure where it’s going.
And this, dear Talent First readers, this is what we call The Messy Middle of Careers.
The messy middle is subtle. It sneaks up on high performers. It’s not dramatic. There’s no catastrophic failure, no sudden burnout, no epic meltdown.
Instead, it’s a slow-burning question that wakes you up at 3 AM:
“Is this… it?”
2. Why the Middle got so “Messy”
2.1 Careers used to be relatively “linear”
Your parents probably had one or two major job changes, that’s it. They chose a “track” early and stuck to it. Even if they didn’t love their jobs, the path was clear, and that gave it meaning.
If you analyzed careers for Baby Boomers or Gen X, they were relatively linear:
Relationships: they belonged to a rather "closed", local group of friends and acquaintances (sometimes around religion)
Education: they went to university only once (if ever)
Jobs: they worked at the same 1-2 companies for most of their careers years
Retirement: they retired (and had the certainty they would)
But that world is gone.
2.2 The new generations simply face a tougher landscape
Millennials and Gen-Zs are navigating an entirely different world:
Relationships: we belong in a much more liquid, international and moving group of people (more interest-based)
Education: we need to adopt a "life-long" learning attitude. We will always need to learn new things and adapt to change, be it with traditional university or new ways of developing skills.
Jobs: we change jobs more often (exactly every 2.8 years for white-collar millenials)
Retirement: we do not even know if we will retire and who will pay for it.
We overall live in a world of more uncertainty (global crises, fast technological changes, etc.) and more pressure (from productivity culture, personal branding, “finding your passion”, etc.).
Mix all of that and you have a generation primed for a mid-career identity crisis.
Today, our careers are shaped less like ladders and more like jungle gyms. Up, sideways, down, across - anything goes.
And with each move, the trade-offs pile up.
Should I optimize for salary or learning?
Should I go into management or become an expert?
Should I stay loyal to my company or explore new adventures?
Should I get that MBA? Or is it a waste of time and money?
Suddenly, you’ve spent 7 years in Consulting or Product or Fiannce or Sales or Ops, and you’re asking yourself: “Was this the right bet?”
You might even be great at your job: but feel like you're climbing a ladder you’re not sure you want to be on.
2.3 Comparing yourself does not help
In a recent survey by Lenny’s Newsletter, 37% of tech workers admitted to having career doubts. The number jumps even higher among professionals with 7 to 15 years of experience.
Why? Because this is the stage where it gets real.
You’re no longer riding the excitement of “firsts.” You’ve shipped products, led teams, grown users. You’ve ticked off KPIs and earned promotions.
But you haven’t “made it” yet: not in the way you thought you would. And the benchmarks keep shifting. The titles get fancier, but the purpose gets fuzzier.
Meanwhile, LinkedIn makes it look like everyone else has it figured out. That ex-colleague is now a VP. That old uni friend just raised a Series B. That startup you turned down just got acquired.
It’s a cocktail of comparison and existential dread.
3. What to do if you’re in the “Messy Middle”
You’re not broken. You’re just in transition. Let’s talk about how to navigate it.
3.1 Remain calm: reflection is a feature, not a bug
If you’re questioning your path, it means you’re paying attention.
This is not a breakdown. It’s a breakthrough in disguise.
Before jumping into action mode, sit with the discomfort. Journal. Go on a long walk. Talk to a friend who knows you deeply. Sometimes, naming the feeling is half the battle.
The reality is that our world happens so fast that many people of this generation don’t even know themselves well enough to start thinking about a change.
Ask yourself:
What do I actually enjoy doing at work?
What drains me?
When have I felt most energized in my career?
What do I want my legacy to be?
What are my key strengths? Where am I truly better than most of my peers?
What tradeoffs am I willing do make? (salary, location, working hours…)
What is important for me outside of work?
The goal is not immediate clarity: it’s emotional honesty. Coaching tools such as “Johary’s Window” or the “Wheel of Happiness” are useful for this.
3.2 Take ownership: your career, your decisions
It’s tempting to wait for your manager, your mentor, your HR partner to show you the next step.
But the truth is: No one’s coming.
In the messy middle, the people around you don’t have a roadmap for your life. Only you do.
Take responsibility. Update your resume. Reach out to that contact. Explore that idea. Sign up for that course.
The sooner you move from passive to active mode, the sooner momentum returns.
3.3 Be optimistic: the future is brighter than you think
Yes, the world is messy. But it’s also full of opportunity, and brighter than ever if you follow almost any economic metric out there.
Talent is more mobile, more connected, and more empowered than ever. Remote work, startups, creator tools, global networks: they’ve lowered the barriers to change.
People reinvent themselves all the time. We’ve seen marketers become founders. Engineers become VCs. Consultants become community builders. And yes: sometimes people return to what they were doing, just with more clarity.
Careers are long. Don’t judge your journey by someone else’s highlight reel.
3.4 To find the answers, seek the connections
Often, the next step comes through someone else’s story.
A conversation with a mentor who took a similar leap. A coach who sees your blind spots. A peer who shares your doubts. A psychologist who helps you untangle your values.
The messy middle is not a solo mission. It's a stage best navigated through community.
At Nova, we’ve seen again and again: one conversation can unlock years of confusion.
So the next step is to start moving and make those connections happen: join networks (like Nova!), go to events, get yourself a mentor and start opening up. The answers will come as a result.
Taking on Mastercard’s moto: connections can be “priceless”.
3.5 Stay hungry, stay foolish
Steve Jobs wasn’t just being poetic. There’s deep wisdom here.
Although it may sound obvious, your real limits are always as high ow beloe where you set them. The risk is not aiming too high: it’s aiming too low and hitting it.
Actually, when we interview top CEOs and successful founders, they rarely regret having done things: they regret not having tried them.
So ask yourself: what will I regret not having tried as I retire?
And optimize for lack of regret.
4. Stories from the Nova Community to inspire you
4.1 Mentoring as a path to purpose
Mauro joined Nova’s Mentoring Program out of curiosity. What he found was much more than a professional exchange. It was a way to build deep, human connections.
Over time, some of his mentees became close friends. Mentoring didn’t just allow him to give back; it gave him a new sense of purpose.
He told us:
4.2 The introduction that changed everything
When Tomás joined Nova, he didn’t expect it would shape so many chapters of his life, but it did.
Through the network, he met the person who introduced him to his current company. He also found the perfect roommate for an international move and built friendships that have stood the test of time.
In his words:
4.3 Clarity, coaching, and a new chapter
Laura was at a crossroads in her career and unsure of her next move. That’s when she joined one of Nova’s Coaching Programs.
With support from her coach and the Nova network, she gained clarity, identified her priorities, and landed a role as Head of Asset at Almond, a perfect next step.
She shared:
Find more inspiring journeys on our website. Will yours be one of the next Nova stories?
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