Overwhelmed By Information: Which Career Path Should You Pick?
How to be confident about your next move
You’re doing everything right. Networking. Coffee chats. LinkedIn research. Informational interviews with people three steps ahead of you on the path you think you want.
And somehow, you’re more confused than when you started.
Every conversation surfaces a new option. Every person you talk to has a slightly different take on what you should do. You started with one possible direction; now you have seven. Your notes app is full of job titles, company names, “maybe I could...” ideas. None of them feel wrong, exactly. But none of them feel like the thing either.
So you keep researching. Keep talking. Keep adding to the list. And the moment when you actually have to choose—apply, commit, tell people what you’re doing—keeps getting pushed further out.
This is what being stuck looks like for smart, capable people. Not paralysis from lack of options. Paralysis from too many.
Here’s what I’ve learned from coaching people through this: the problem isn’t that you need more information. It’s that you don’t have a filter. You’re gathering data without a framework for making decisions. So every new input just adds to the noise.
Amelia came to me in exactly this spot.
She’s a legal operations professional with 12 years of experience at companies you’ve heard of—a major creator platform, a digital media company, creative agencies. She’d been exploring a pivot for years. She knew what she wanted: to help creative entrepreneurs build their businesses. She’d even done the work before, helping a friend in another country launch a business and quit their day job.
But she couldn’t land the plane. She’d had dozens of informational interviews. Each one gave her more to think about. And thinking had become a way of not deciding.
In our first session, I built her a Pivot Pathfinder—career paths, job titles, networking templates, a 3-month roadmap. I thought I was giving her clarity.
She emailed me back:
“Many of the suggestions are similar to what I have already done... I’d like to hone in on what makes my assets unique before jumping to paths I feel I’ve already explored.”
She was right. I’d given her more information. What she needed was a filter.
So we did a second session. And what emerged might help you if you’re in the same spot: drowning in possibilities, unable to choose, wondering why all this “exploring” isn’t getting you anywhere.
What We Did Differently
In the first session, I asked Amelia what she wanted and then gave her paths to get there.
In this session, I flipped it. Instead of starting with destinations, I started with a description of who she is when she’s working at her best—based entirely on a detailed email she sent me after our first conversation.
I read it aloud to her:
You’re the person organizations and leaders call when things are complex, high-stakes, and stuck. Not because people aren’t talented, but because no one is sitting in the space between strategy and execution, between legal and business, between what leadership wants and what teams can actually deliver.
You walk into situations where there are multiple smart people talking past each other, where constraints feel like roadblocks instead of design parameters, and where trust has either broken down or never been built. You listen. You learn the players. You figure out what’s actually true versus what’s being assumed. Then you do something most people can’t: you hold the whole picture while helping each person see their part in it.
You don’t just create structure. You shape decisions.
Then I read her a hypothetical week—Monday through Friday—of what her ideal work life might look like. Not job titles. Not industries. Just: here’s what you’d be doing on a random Tuesday.
And I asked her to rate each day, one to ten.
What Emerged
Monday: A call with a founder who’s overwhelmed by compliance and contracts. You help her see what decisions she’s actually facing. She leaves with a clear action list.
Amelia’s rating: 5. “This is my bread and butter. It’s a regular day. Not bad, but not getting me out of bed.”
Tuesday: A workshop with a creative agency whose operations are a mess. You observe how they work, find the friction, co-design a solution.
Rating: 3. Something about this didn’t land.
Wednesday: A longtime client texts you when things get hairy. Today it’s a partnership negotiation going sideways. You help them see the other side’s perspective and find their walkaway point.
Rating: 7. “What resonated was the long-term relationship.”
Thursday: You fly to meet a contractor who’s built a $2M business and is drowning in complexity. You shadow how he works, then whiteboard together. You leave energized.
Rating: 10. “I’m flying in, I’m observing, I’m not forcing change.”
Friday: You’re writing a debrief for yourself—what patterns are you seeing, where are you most useful. A potential client calls, referred by someone you helped years ago. They say, “She told me you’re the one who gets things unstuck.”
Rating: 10. “I love retrospectives. This is hugely important.”
The Insight
When Amelia rated Friday a 10, I knew something had clicked.
Friday wasn’t a client day. It was an entrepreneur day. Reflecting on patterns. Building your own playbook. Getting referrals from past work. That’s what it is to run your own thing.
And she loved it.
But here’s what surprised me more: she rated Tuesday—the agency workshop—a 3. That was one of the paths I had mapped in the original Pathfinder. On paper, it fit. In her body, it didn’t.
This is why the exercise mattered. You can’t think your way to the right career. You have to feel your way there.
Want to do this exercise for yourself? In the Progress Plan, I walk you through how to map your own ideal week—and use your body’s response to cut through the mental noise.
The Filter That Changed Everything
After the Monday-through-Friday exercise, I shared something that reframed the whole conversation:
The question is no longer “what do I do.” You’re clear on that. The question now is: who pays for this?
That’s a market question, not an identity question. And you can only answer it by testing—not by thinking.
Amelia had been doing informational interviews for weeks. Talking to people in every industry. And feeling like she wasn’t landing anywhere.
The problem wasn’t the conversations. It was that she didn’t have a filter. She was gathering information without a decision framework.
So we created one. Three lenses to evaluate any potential client or employer:
Pain: Do they have the problem you want to solve? Are they actively stuck, overwhelmed, needing someone to come in and unstick things?
Budget: Can they actually pay? Not “should they pay”—do they have money allocated for this kind of help?
Proximity: Can you reach them in the next 30 days through your existing network? Warm paths, not cold outreach.
The sweet spot is all three. But if you have to pick, start with proximity. Who’s closest to saying yes?
This is the filter that turns endless exploration into actual decisions.
The Progress Plan includes a worksheet to run every opportunity through this filter—so you stop collecting options and start eliminating them.
The Opportunity That Was Already There
Midway through the session, Amelia mentioned something almost casually:
“A former coworker is starting a consulting business with a more senior partner. They’re helping founders get to execution stage. They think my profile is a good fit to join as a consultant. They want to get started in the next two to three months.”
I stopped her.
“How does this rate on the Monday-through-Friday scale?”
She said: “A 10. For the season I’m in, it lets me test the waters without a huge pivot. I have bandwidth. It excites me.”
This opportunity checks every box:
She gets to do the work she described loving
She learns how to run a consulting business by watching someone else do it first
She gets exposure to different client types to see where she’s most impactful
She doesn’t have to build a website or figure out marketing yet
She gets paid while she figures it out
Sometimes the path forward isn’t a grand plan. It’s just saying yes to the thing that’s already in front of you.
What About Full-Time?
Amelia isn’t necessarily becoming an entrepreneur. She might end up in a full-time role. So I thought through what titles might fit someone with her operating system.
The answer: roles that mostly don’t get posted. They get created for specific people.
Chief of Staff — the connective tissue between a CEO and the rest of the org
VP of Strategic Initiatives — the person who parachutes into the hardest cross-functional problems
Head of Business Operations — not process-and-systems ops, but making-the-business-work ops
General Manager — running a semi-autonomous business unit or region
The common thread: these roles require someone who can hold the whole picture, build trust fast, and move fluidly across functions. That’s Amelia.
But here’s the catch: she won’t find these roles on a job board. She’ll find them through relationships—by being in conversations where someone says, “I don’t know exactly what I need, but I need someone like you.”
Which is exactly what happens when you’re out in the world doing the work, not just researching the work.
The Fears That Keep You Stuck
As we talked, three fears kept surfacing—ones I hear from almost everyone in Amelia’s position.
“What if I’m the first to be fired?”
Amelia worried that working “at the seams”—not in a clear silo with a clear title—makes you expendable when budgets get tight.
Two responses:
First, get real data. Instead of letting the fear spin in your head, ask about it directly in your conversations: “When companies cut costs, what roles go first? What roles are protected? Why?”
Second, consider the alternative. The “safe” job—the one with a clear title and a clear silo—might feel more stable. But it’s also the one that leaves you bored, checked out, and back in this same spot in two years. The roles that fit you best are ones where you’re so embedded in how things actually get done that cutting you would hurt.
The goal isn’t to be unfireable. The goal is to be so valuable that people keep pulling you back in. Which, by Amelia’s own account, is already happening.
“What if I have to market myself?”
This fear was underneath the surface: if she does this work publicly—tells people, updates LinkedIn, takes clients—she’s exposed. What if it doesn’t work? What if people judge?
Here’s the reframe: you’re not marketing. You’re just making it easier for the right people to find you.
People already text Amelia years later when things get hairy. People already call her “Amazing Grace” and “the glue.” That’s word of mouth. That’s referrals. That’s already happening.
“Marketing” just means letting that happen at slightly larger scale. For now:
Tell 10 people you trust
Update your LinkedIn headline
Say yes when someone brings you an opportunity
No website. No content calendar. No personal brand. Just honesty about what you’re up to.
“What if I pick the wrong niche?”
Amelia kept saying she needs to pick a niche to be credible. But here’s the thing: you don’t find your niche by thinking. You find it by doing.
The consulting opportunity will expose her to different client types. Some will energize her. Some will drain her. Some will pay well. Some won’t. After 90 days of actual work, she’ll have real data about where she wants to specialize.
Trying to pick the niche before doing the work is like trying to pick your favorite restaurant in a city you’ve never visited. You have to eat a few meals first.
The niche will reveal itself. Your only job right now is to stay in motion.
The Progress Plan includes daily exercises to work through each of these fears—turning them from vague anxiety into concrete questions you can actually answer.
What Progress Actually Looks Like
If you’re like Amelia, you might be measuring progress as “I got the job” or “I found my niche.” But at this stage, that’s the wrong metric.
Progress:
You can describe what you do without defaulting to a job title
You know which kinds of work energize you vs. drain you
You have a live opportunity to test the work (even imperfect)
Each conversation gives you data that helps you decide, not just information that adds to the pile
You can say “I want more of this” or “I want less of this” with conviction
Not progress (yet):
Knowing your exact niche
Having a five-year plan
A polished website
A perfectly crafted pitch
Certainty
The homework isn’t to figure it all out. It’s to run enough experiments that the path becomes clear.
Key Takeaways
1. More information isn’t the answer. A filter is.
You’re not lacking data—you’re lacking a framework. Pain, Budget, Proximity. Run every option through it.
2. Feel first, then think.
Your body knows things your brain is still arguing about. A 3 feels different than a 10. Pay attention.
3. Proximity is the tiebreaker.
When you’re overwhelmed, start with who’s closest to yes. Not the best opportunity in theory—the one you can actually reach.
4. The opportunity might already be there.
While you’re researching, something might be sitting right in front of you. Look for what you’ve been dismissing as “not quite right” or “too easy.”
5. You don’t find your niche by thinking. You find it by doing.
Stop trying to pick the perfect path before you’ve walked any of them. 90 days of work will teach you more than 90 days of research.
What This Means for You
If you’re in a similar spot—clear on your skills but fuzzy on where to apply them, doing informational interviews that feel like spinning, caught between entrepreneurship and employment—here’s what I want you to walk away with:
Stop researching. Start testing. You don’t need more information about what’s out there. You need information about what works for you. And you can only get that by trying things.
Use your body as a compass. When you imagine a version of your work life, notice what happens physically. Expansion or contraction? Warmth or cold? Curiosity or dread? Your nervous system has data your brain doesn’t.
Say yes to the thing in front of you. If there’s an opportunity already there—even imperfect, even small—consider taking it. You’ll learn more in 90 days of doing than in a year of planning.
Your job title doesn’t exist yet—and that’s okay. If you’re someone who works at the seams, who sits in the “third space,” who holds the whole picture—there probably isn’t a clean title for what you do. Describe the function. The title will come later, or it won’t matter.
Turn This Into Action
Reading about Amelia’s session is one thing. Actually breaking your own loop is another.
I created a Progress Plan called “7 Days to Find Your Filter” that turns the key insights from this session into daily exercises you can do in 5–20 minutes.
By the end of the week, you’ll have:
A clearer picture of what energizes you (using the Monday-Friday mapping exercise)
A filter for every opportunity (Pain, Budget, Proximity—applied to your actual options)
Questions that generate decisions, not just information (for your next conversations)
A reframe for the fears keeping you stuck (expendable, visible, wrong niche)
A 90-day container with real milestones so exploration doesn’t become procrastination
One concrete step taken toward the opportunity that might already be in front of you
If you’re stuck in the same loop Amelia was—drowning in options, unable to choose, watching “research” become a way of not deciding—this is the week you get unstuck.
