Decision Making 201: When you’ve weighed every option and still can’t decide
You’ve made tough calls before. So why does this one feel different?
Welcome to Reframed, where high-achieving professionals come to rethink their careers. Because doing things the “right” way only works if it’s actually right for you.
I'm Ashley Rudolph—a former tech executive turned coach for leaders and next-gen execs in the creative, tech, and lifestyle industries.
I’m feeling inspired this week, still on a high after Cowboy Carter last week.
Happy Memorial Day!
I’ve been thinking a lot about decisions lately. The kind where you’ve run the numbers. Made the pros and cons list. Asked your mentors. Vent-texted your best friend. And still, you feel stuck.
Not because you’re unsure.
Not because you’re unqualified to make the call.
But because the usual tools don’t work when the stakes are personal. When you’re making a choice that’s not just about strategy or outcomes.
This is Decision Making 201.
THE CONTEXT: WHAT I’VE LEARNED AND OBSERVED WHEN MAKING HARD DECISIONS
I’ve always been someone who makes decisions quickly. Whether it’s a career shift, a creative idea, or something I want to accomplish in my business, I trust myself to act. I’ve made big decisions without having all the answers and I’ve rarely regretted it.
I’ve also made mistakes.
I’m equally willing to make a call and deal with the consequences.
Like the time I recently decided I wanted to be a guest on podcasts and booked myself on 15+ podcasts in under two months. By myself. With a strategy, some automation, and good old cold outreach.
Decisiveness got me there.
Some of my decisions have worked beautifully. Others taught me lessons I couldn’t have learned any other way. But the through line is this: I move.
What I’ve found over and over is that my approach to decision making mirrors the way many of my high-achieving clients move through their careers.
You’re good at making smart calls. It’s what’s gotten you promoted. It’s what makes people look to you when things are unclear.
You’ve already mastered Decision Making 101—the tactical, logical calls that build careers. You know how to assess risk, weigh trade-offs, and move. It’s what got you here.
But at a certain level, decisions start to shift. They get less tactical…and more personal.
The decisions that feel hardest to make and even harder to execute are the ones that hit close to home. Not just “What’s the right career move?”
But:
What will this decision say about me?
What if I leave security behind and it doesn’t work out?
Am I walking away from something real or something I’ve just outgrown?
How much can I push and advocate for myself while preserving my relationships?
This is Decision Making 201 territory. When the questions you’re asking aren’t just about outcomes, they’re about identity.
And that’s exactly why logic alone doesn’t cut it anymore.
CONTEXT: WHY THIS HAPPENS TO HIGH ACHIEVERS
Why Smart People Still Get Stuck
When my clients come to me stuck, it’s not because they’re indecisive. It’s because the decision they’re wrestling with has weight. History. Real-life consequences.
They’ve already done what most high-performers do:
Made the pros and cons list (maybe 3…lol)
Asked their smartest friends and most trusted mentors for advice
Tried to talk themselves into the “safe” choice or waited for something to make the choice for them
And still…they’re stuck.
Because they’re trying to solve an emotional decision with a logical tool.
And it just doesn’t work.
KEY TAKEAWAY
It’s not confusion. You’re making a decision you haven’t given yourself permission to make yet.
STRATEGIES & TACTICS FOR NAVIGATING COMPLEX CAREER PROBLEMS
How I Guide High-Achievers Through the Hard Calls
When someone brings me a real, live, high-stakes decision, we don’t rush to the answer. We get clear.
Here’s the general process I take them through. This isn’t a script, it’s part of the strategy:
1. Gut Check
When you imagine saying yes, how do you feel? Relief or tightness? Energy or dread?
Then we zoom out: If both options disappeared tomorrow, what would you wish you had chosen?
This gives us perspective and often surfaces a path they haven’t fully considered.
2. Values Alignment
Which option supports the story you’re writing for your life? Not the one that looks good to others. The one that feels right for you.
3. Future Self Test (10/10/10 Rule)
How will this decision feel in 10 minutes?
In 10 months?
In 10 years?
Sometimes what feels impossible now will feel like a turning point later. The 10-year version of you knows.
4. Opportunity Cost
Every “yes” is a “no” to something else. What are you giving up and are you okay with that?
5. Reality Mapping
What happens next? Literally, what are the first three steps you’d need to take if you said yes (or no)?
If those steps feel impossible, it’s a sign. Not that you’re weak but that the move might be out of alignment.
→ IN CASE YOU MISSED IT
I started a new series last week called “Open Tabs”. A quick 5 minute read with curated articles and links that have been making their way into my client calls, dinner convos, and group chats. It’s v good.
PRACTICALLY SPEAKING: A CLIENT TRANSFORMATION
A Real Story: When the Personal Made It Hard
Not long ago, a client (we’ll call her Alice) booked a one-time strategy session with me because she was stuck. And not in the “I don’t know what to do” kind of way. I believe she did know deep down, but the weight of the decision made it nearly impossible to choose.
She’d been offered a leadership role created specifically for her by someone she deeply respected. A current manager, mentor, and friend; someone who had championed her work and pitched her for succession in the future. It was personal. Trust-based. And the offer came with workable comp (albeit lower than what she made before) and an executive title.
Everyone around her said the same thing:
You’d be crazy to turn this down in this market.
It’s good money.
The other roles aren’t guaranteed.
You can’t afford to be risky right now.
And I didn’t push back on any of that.
Instead, we got curious.
We talked about what it would actually look like to take this job, knowing she’d keep looking for something better. Could she accept it now and decline gracefully later? Or would that burn the very relationship she cared most about preserving?
This is where a lot of people try to logic their way through it.
Take the offer now, they say. If something better comes along, you can always leave.
But that calculus starts to shift when you’re stepping into senior leadership, when your role doesn’t just affect you but an entire team, department, and company strategy. Joining at that level and leaving soon after doesn’t just inconvenience people. It creates ripple effects. It impacts morale. It alters momentum. It shapes narratives about you that you may not be around to correct.
She wasn’t just evaluating a job. She was evaluating the kind of leader she wanted to be and the kind of story she wanted to tell through her choices.
We also dug into the opportunity itself. Could this be a stepping stone or an exciting detour? When she pictured telling this part of her professional narrative five years from now, did it feel expansive or like a compromise?
And finally, we turned to finances. The offer she was weighing was more than $75K less than what she’d earned in her previous role. It was workable but she knew she could command more.
After talking all of this through, she was clear: it didn’t excite her.
Not the work. Not the environment. Not the direction.
And finally, she told me about the other offers in motion, the signals she’d received from hiring managers, and the real traction she was seeing. We weighed the odds together. She wasn’t gambling. She was making a clear, informed bet on herself.
And in the end, she did what most people were afraid to do.
She said no to the “safe” option.
To the role created for her.
And…
15 minutes after she hung up the phone to decline the offer, one of those “not real yet” opportunities became real.
A verbal offer. Fully aligned. Nearly six figures higher.
KEY TAKEAWAY
She wrote me later: “I’m learning that I need to get back to trusting my gut and letting go of the things that don’t serve my goals to make space for those opportunities that do.”
And that’s exactly what she did.
UNPACKING HER SUCCESS: WHY THIS WORKED SO WELL
Now I want to be clear about something:
I’m not a “bet on yourself” and “step out on faith” with Natasha Bedingfield playing in the background kind of coach.
That’s not what I’m about.
This isn’t about romanticizing risk. It’s about making measured, informed decisions that take your full context into account: your values, your finances, your relationships, your goals, and yes, your energy.
And part of what makes this work so effectively is how the conversation unfolds.
It’s not just a framework. It’s the right conversation, with the right questions, at the right time.
I ask the follow-up questions you don’t think to ask yourself.
I bring in context where you might have blind spots.
And I push, gently but intentionally, when I can tell you’re underestimating your own talents.
Sometimes that means helping someone reframe what they’ve accomplished so they stop selling themselves short.
Sometimes it’s helping them recognize that the “safe” choice isn’t actually safe at all.
And sometimes, it’s just holding enough space for their real desires to come through, uninterrupted by fear, logic, or other people’s expectations.
WORK WITH ME
If you’re feeling stuck (even though you’ve thought things through from every angle) this is exactly the point my clients are at before I help them get to clarity.
My one-time strategy sessions are designed to help high-achievers make decisions that align with their ambitions and career goals.
I only take one strategy session client per month, which means I’m only taking five more in 2025.
Book yours here.
THE WRAP UP: CLOSING THOUGHTS
The Bigger Picture: Decision-Making Is a Leadership Skill
Here’s what I want you to take with you: good decisions don’t have to come from certainty but they do come from clarity.
And clarity comes from knowing who you are, what you want, and what you’re no longer willing to compromise on.
So the next time you’re on the brink of spiraling over a hard decision, I want you to remember this:
You don’t need more time.
You don’t need more opinions.
You need to know what most important to you.
And that truth? It’s been with you the whole time.
Good luck! See you next week.
Ashley
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