A Framework for Making Career Decisions in an Imperfect Market

Building a better work-life.

Happy Friday 🎉

“When do you know when to take the opportunity at hand, even if it’s not perfect, versus continuing to search for something that might seem perfect? Is there such thing as perfect?”

This question landed in my inbox last week from “J”, a recent MBA grad who’d just been let go. She had a compelling opportunity in front of her—a contract role with a dermatologist’s skincare brand that had just landed a new account. The role offered growth potential, industry experience she craved, and flexibility in title and compensation. But it wasn’t a W-2 position, and it wasn’t “perfect.”

J’s dilemma isn’t unique. In today’s brutal job market, many of us find ourselves weighing imperfect opportunities against the hope of something better. The question isn’t just about this specific role—it’s about how we make career decisions when perfection feels both impossible and necessary.

The Framework: What’s It Giving You vs. What’s It Taking Away?

Instead of chasing the mythical perfect opportunity, I’ve found it more useful to think in terms of trade-offs. Every opportunity has an opportunity cost. The question becomes: what is this role giving you, and what is it asking you to give up?

What the opportunity was giving her:

  • Ground-floor experience at a growing company
  • Exposure to the beauty/wellness industry she wanted to enter
  • Flexibility to shape her role and title
  • Skills development across multiple functions
  • Potential for significant growth (“sky’s the limit”)

What it was taking away:

  • Traditional W-2 benefits and security
  • Time to continue job searching
  • Experience within a large organizational structure
  • Networking opportunities in bigger companies

But here’s what I’ve learned coaching hundreds of job seekers: the analysis can’t happen in a vacuum. You have to factor in market reality.

The Job Market Reality Check

Before you can evaluate any single opportunity, you need an honest assessment of your alternatives. In J’s case, she’d just gone through an interview process for what seemed like an ideal role—and didn’t get it. The market is challenging enough that even strong candidates with relevant experience are getting turned down.

So the first question isn’t “Is this opportunity perfect?” It’s “What are my realistic alternatives, and how long would it take me to land them?”

If you’ve been searching for months with few promising leads, a good-but-imperfect opportunity starts looking very different than if you have multiple offers on the table.

The Long-Term Career Path Perspective

One insight that often gets overlooked: you don’t have to stay anywhere forever. Instead of thinking “Is this the right job?” think “Is this the right next step?”

For J, even if the skincare company didn’t become her dream job, it would give her beauty industry experience that could open doors later. Sometimes the value of an opportunity isn’t in the role itself, but in how it positions you for the role after that.

I always tell job seekers: look at people whose careers you admire. What titles did they hold? What companies did they work for? Sometimes what looks like a lateral move or a compromise actually sets you up for a bigger leap later.

When “Perfect” Becomes the Enemy of Good

The pursuit of the perfect opportunity can become a trap. While you’re waiting for something that checks every box, you’re missing chances to:

  • Build new skills
  • Expand your network
  • Prove yourself in a new industry
  • Generate income and momentum

Perfect is often just another word for familiar. The “perfect” job might be the one that looks exactly like what you’ve done before—which means you’re not growing.

The Decision Framework in Action

Here’s how to apply this thinking to your own career decisions:

  1. Reality check your market position: How many truly viable opportunities are you seeing? How long have you been searching?
  2. Map the trade-offs: Create two columns—what you gain vs. what you give up. Be specific and honest.
  3. Think two jobs ahead: Will this role position you better for future opportunities? What skills or experience would you gain?
  4. Consider the opportunity cost of waiting: What are you not doing while you search for perfect?
  5. Trust your instincts about growth: Does this opportunity excite you, even if it scares you a little?

The Bottom Line

There’s no such thing as a perfect opportunity—there are only opportunities that align with what you need at this moment in your career. Sometimes what you need is stability and benefits. Sometimes what you need is growth and new experiences, even if they come with uncertainty.

J ultimately had to decide whether the potential for growth outweighed the security she’d be giving up. But more importantly, she had a framework for making that decision confidently, rather than second-guessing herself into paralysis.

The next time you’re evaluating an opportunity that’s “good but not perfect,” remember: the goal isn’t to find the perfect job. It’s to make the right next move for where you are now, and where you want to be two jobs from now.

What trade-offs are you weighing in your career right now? I’d love to hear about the opportunities—perfect or imperfect—that you’re considering.


We got this – together 💪

x Claire

PS I have the capacity to coach a few more clients this summer, reach out if you’re interested in a complementary session.

In this issue:

Program

Join a Paid Pod in June

Webinar

How to Improve Your Resume With AI (Recording)

Coach Spotlight

How to Calculate Your “Freedom” Number

📣 Job Seekers

Join a June Paid Pod!

When + Where

June 2-30, Virtual @ Mutually Agreed Upon Time

What

Job Search Strategy + Materials and 4 Live Sessions

Cost

$17/day for 30 days

Stop throwing resumes into the void and start positioning yourself as the business solution employers desperately need.

This isn’t just another career coaching program—it’s a complete strategic transformation that gets results. Whether you’ve been searching for months, feeling overwhelmed by conflicting advice, or watching perfect opportunities slip away, this program rewires your entire approach. Plus, it’s the only job seeker program that creates all of your materials for you.

Kicking off on June 2nd, you’ll receive:

📋 Your personalized 80+ page job search strategy document + materials
👥 Weekly group coaching sessions with direct feedback
💬 Scripts that transform your experience into compelling business cases
🛡️ Well-being strategies tailored to your personality type

Deadline to register is May 26th.

video preview


In a recording of our latest webinar, Claire Wasserman and resume expert Ashley Cash reveal the strategic system that gets interviews — not just applications. This isn’t generic resume advice. It’s a complete reframe: stop thinking like a desperate job seeker and start positioning yourself as the solution to business problems.

Whether you’re career pivoting, struggling with ATS systems, or spending hours customizing resumes, this session transforms your entire approach. In this session, we cover:

📊 The 7-second reality of how hiring managers actually review resumes
🔍 The AI prompt that decodes job descriptions to reveal business pain point
💡 How to quantify impact when you “don’t have metrics”
🤖 Srategic AI prompts that do the heavy lifting while you do the critical thinking
✂️ Live resume makeover showing exactly what to cut and why

Coach Spotlight: Tess Waresmith

How to Calculate Your “Freedom” Number

Ever wonder how much money you actually need to stop working someday?

Most of us avoid that question because it feels overwhelming especially when you’re short-on-time, feel like you’re “bad” at money, or are worried you’re too far behind to catch up.

A powerful place to start is to calculate your financial independence number which is the number you would need to hit to be able to live off your assets comfortably (think IRA, 401k, or other investing accounts).

It gives you clarity. A target. A sense of control over your future, even if you’re not ready to retire anytime soon.

Here’s how to calculate it:

  1. Estimate how much money you’d want per year in retirement. (Example: $80,000/year to live comfortably)
  2. Multiply that number by 25. This is what’s called the 4% rule, a guideline that assumes you can safely withdraw 4% of your invested money each year without running out. In this case, your financial independence number would be: $80K × 25 = $2 million
  3. Don’t panic if this number is high. Investing is a great way to build compound wealth and the worst case scenario if you start focusing on your money now is that you get closer to this number.
  4. Start planning how to get there by reviewing your monthly cash flow and seeing how much you can invest right now.

This isn’t about retiring tomorrow. It’s about knowing your number so you can start moving toward freedom, confidence, and options on your own terms.

If you want help calculating your own number and seeing what it would take to reach it, join Tess Waresmith’s FREE training that walks you through calculating your own financial independence number, key things to consider, and a compound interest calculator you can use to start figuring out how much more you can invest and how your money could grow. Get started 👇

x Claire Wasserman

I help women embrace their worth and activate their potential. I’d love to support you – learn more here!

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