Building Your Dream Career: Part 2 - Finding Opportunities That Actually Fit (Even When the Market is Terrible)
In Part 1, you did the hard work of defining your priorities and creating your career compass. Now comes the strategic part: using that compass to navigate a job market that's flooded with talent and incredibly competitive.
Let me set the scene for where we are right now. It's late October 2025. My contract ended this week. And I'm watching the job market flood with incredibly talented tech professionals as Amazon executes another round of massive layoffs. People with impressive resumes, years of experience at top companies, and strong technical skills are all competing for the same limited set of open roles.
When I tell people my contract ended, they immediately ask: "Oh no, are you okay? How's the job search going?"
Here's the thing: I'm not actively job searching in the traditional sense. I'm strategically evaluating opportunities. I have the financial cushion to be selective. I'm not applying to anything that's just "good"—I'm only pursuing opportunities I consider "great." And I recognize that this is an incredibly privileged position to be in right now.
Most people in tech in 2025 don't have this luxury. The market is brutal. Job security is a myth. And having the financial runway to be picky is rare.
But here's what I want you to understand: regardless of your financial situation, you can still be strategic. The tactics change based on your circumstances, but the framework remains the same. Whether you're desperate for any income or selective about the perfect fit, you're making choices—and smart choices come from having a clear framework.
This post is about how to find and evaluate opportunities when the market is oversaturated, competition is fierce, and you need to stand out among hundreds of qualified candidates. It's about making strategic decisions that align with your priorities, whether you're taking the first acceptable offer or holding out for the ideal role.
Let's get tactical.
📥 Tool to Work Through This: Job Opportunity Evaluation Kit
I've created a comprehensive kit to help you research companies and evaluate opportunities against your priorities. Includes a company research template, job evaluation scorecard, interview questions guide, and decision-making framework.
Interview Questions Guide (including GHC-specific approaches)
Opportunity Tracker Spreadsheet
No signup required. Fill it out for every opportunity you're seriously considering.
The Reality Check: Understanding Your Current Position
Before we dive into finding opportunities, you need to honestly assess where you are right now. Because your strategy will be dramatically different depending on your circumstances.
The Desperation Zone (0-2 Months of Runway)
Your reality: Bills are due. Savings are gone or nearly gone. You need income, fast. The Amazon layoffs mean you're competing with incredibly qualified people for every role.
Your strategy: You're in survival mode, and there's no shame in that. Your non-negotiables from Part 1 are critical here—those are your floor. Everything else is negotiable for now. Your goal is to secure income that meets your physiological and safety needs while keeping your career trajectory alive.
What this means: You might take a contract role, a role slightly below your level, or a job at a less-than-ideal company if it pays your bills and doesn't actively harm your career. This isn't failure—it's strategic survival. You're making a smart decision based on your current reality.
The Selective Pressure Zone (3-6 Months of Runway)
Your reality: You have some time, but not unlimited. You can be somewhat selective, but you also need to move with purpose. You're competing with laid-off Amazon engineers who are also in this zone.
Your strategy: Focus on opportunities that meet your non-negotiables plus 2-4 of your top priorities. You can't afford to hold out for perfect, but you can be strategic about which imperfect opportunity you choose.
What this means: You're balancing urgency with fit. You'll apply broadly but evaluate carefully. You'll pursue multiple opportunities simultaneously and make trade-offs consciously, not desperately.
The Strategic Position Zone (6+ Months of Runway)
Your reality: You have financial cushion. You can be patient and highly selective. This is where I am right now—I can wait for opportunities that truly align with my priorities.
Your strategy: Hold out for opportunities that meet your non-negotiables and strongly align with your top priorities. You can afford to say no to roles that are just "good" and wait for roles that are "great."
What this means: You're playing the long game. You can be picky about culture fit, growth opportunities, and alignment with your values. You can walk away from offers that don't feel right. You can invest time in networking and relationship-building rather than frantically applying to everything.
If you're currently employed: Congratulations, you're in the best position. You can be highly selective and only move for opportunities that are clearly better than what you have. Don't let FOMO or the "grass is greener" mentality push you to leave something good.
Be honest about which zone you're in. This determines your entire job search strategy. If you're in the Desperation Zone, there's no shame in that—it's the reality many tech workers are facing in 2025. If you're in the Strategic Position Zone like me, recognize that privilege and use it wisely.
The 2025 Market Reality: Amazon Layoffs and What They Mean
Let's talk about what we're all seeing right now. Amazon's layoffs have flooded the market with experienced, talented engineers—people with impressive resumes, strong technical skills, and years at a FAANG company. They're competing for the same roles you are.
What this means for you:
If you're also from a big tech company: You're competing with people with similar credentials. You need to differentiate based on specific skills, projects, and culture fit.
If you're not from big tech: Don't assume you can't compete. Many companies are specifically looking for people who AREN'T from the Amazon/Meta/Google monoculture. Bring your unique perspective, your different experience, your fresh approach.
For everyone: The bar for "good enough to get an interview" just got higher. You need to be more strategic, more targeted, and more intentional in every application.
The good news? Companies are still hiring. They're just being incredibly selective. Which means if you can position yourself as exactly what they need, you have a shot.
Where to Actually Look (Beyond "Just Apply on LinkedIn")
Everyone knows about LinkedIn, Indeed, and company career pages. But in an oversaturated market, you need to go beyond the obvious channels where hundreds of qualified people are competing for the same role.
For Grace Hopper Conference Attendees
If you're attending GHC (or any similar conference), this is one of your biggest advantages. Use it strategically:
Before the conference:
Research which companies will be there and identify your top 10 targets
Use your priority framework to determine which companies align with your goals
Prepare your "pitch" that connects your priorities to what each company offers
Update your resume and have multiple copies (physical and digital)
Connect with recruiters on LinkedIn and mention you'll be at GHC
At the conference:
Company booths: Don't just drop your resume. Have a 2-3 minute conversation about a specific project or team you're interested in. Ask smart questions about culture, growth, or technical challenges. Make them remember you.
Career fair strategy: Tier your targets (just like job applications). Spend 15-20 minutes at Tier 1 companies, 10 minutes at Tier 2, quick resume drops at Tier 3.
Networking events: Focus on quality over quantity. Have 5-10 meaningful conversations rather than collecting 50 business cards.
Technical sessions: Attend sessions from companies you're interested in. Ask thoughtful questions. Connect with speakers afterward.
Follow-up: Within 24 hours, email or LinkedIn message everyone you connected with. Reference your specific conversation. Express genuine interest in specific roles.
After the conference:
Apply to roles within 48 hours while you're fresh in their minds
Reference the conference in your cover letter: "I enjoyed our conversation at GHC about [specific topic]"
If you didn't connect with a company at GHC but wish you had, mention it anyway: "I was at GHC and was disappointed I missed connecting with your team. I'm particularly interested in..."
The Hidden Job Market (For Everyone)
Estimate: 70% of jobs are filled before they're publicly posted. In a flooded market, your odds of landing a role through a public posting are even lower. You need to access the hidden market.
How:
1. Network systematically, not randomly
Reach out to 5-10 people per week in roles/companies you're interested in
Use the informational interview approach: "I'm researching [field/role/company], would you have 15 minutes to share your experience?"
Don't ask for jobs. Ask about their company, their role, what they wish they'd known
If it goes well, ask: "Do you know anyone else I should talk to?"
Keep notes on every conversation and follow up periodically
2. Leverage warm introductions
Go through your LinkedIn connections and identify people at companies you're interested in
Message them directly: "Hey [name], I saw you're at [company]. I'm exploring opportunities there and would love to hear about your experience. Any chance we could chat for 15 minutes?"
If you don't have direct connections, look for second-degree connections and ask for introductions
Alumni networks are underutilized—reach out to people from your school
3. Engage with companies before they're hiring
Follow companies you're interested in on social media
Comment thoughtfully on their posts (add value, don't just say "great post!")
Share their content with your own insights
Attend their webinars, tech talks, or open houses
Contribute to their open source projects if applicable
When they do post a role, you're a familiar name, not a random applicant
4. Work with specialized recruiters
Find recruiters who specialize in your field, not general staffing agencies
Build relationships with 3-5 recruiters who regularly place people in roles like yours
Be honest about your priorities and what you're looking for
Stay in touch even when you're not actively looking
Remember: recruiters work for the company, not you, but a good relationship can be mutually beneficial
Strategic Applications
When you do apply to posted jobs, be strategic—especially when competing with hundreds of other applicants:
1. Apply early
Set up job alerts and apply within 24 hours of posting
After 100+ applications, hiring managers get overwhelmed and your resume gets lost
Your application gets more attention when it's in the first 20
2. Prioritize based on your priority framework
Don't apply to everything—especially in this market, quality matters more than quantity
If you're in Desperation Zone: Apply to anything meeting your non-negotiables
If you're in Selective Pressure Zone: Apply to roles meeting non-negotiables + 2-4 priorities
If you're in Strategic Position Zone (like me): Only apply to roles meeting non-negotiables + 6-8 priorities
3. Use the "tier" system Use the evaluation kit to categorize opportunities:
Tier 1 (Great fits): Meet your non-negotiables + 6-8 other priorities. Spend significant time on these applications. Custom cover letters. Reach out to people at the company. Follow up.
Tier 2 (Good fits): Meet your non-negotiables + 4-5 other priorities. Standard application effort with some customization.
Tier 3 (Survival fits): Meet your non-negotiables only. Quick applications, but only if you're in Desperation or Selective Pressure zones.
My personal approach right now: I'm only applying to Tier 1 opportunities. I have the financial cushion to wait for roles that are truly great fits. If you're in a different zone, your tier distribution will look different—and that's completely valid.
4. Skip the black holes In an oversaturated market, some job postings are time-wasters:
Already filled internally (posting for compliance)
Fishing expeditions (no real intent to hire, just building a pipeline)
Forever open roles (unrealistic requirements, no one ever qualifies)
Role descriptions that are actually 3 jobs combined
Learn to identify these and don't waste your limited time and energy.
Research: Due Diligence Before You Even Apply
In Part 1, you defined what matters to you. Now you need to figure out which companies and roles actually deliver on those priorities. With hundreds of applicants per role, you can't afford to waste time on poor-fit opportunities.
Use the Company Research Template from the Opportunity Evaluation Kit to systematically evaluate each potential employer.
Red Flags to Watch For (In 2025's Market)
Financial instability:
Recent layoffs (check layoffs.fyi and warn.com)
Funding runway under 12 months for startups
Declining revenue for public companies (check earnings reports)
Sudden leadership exodus
Office closures or consolidations
Hiring freezes followed by sudden openings (often backfills, high turnover)
Cultural red flags:
Glassdoor reviews mentioning burnout, toxicity, or poor management consistently across time (look for patterns, not individual complaints)
High turnover in the specific role you're applying for (ask in interviews)
Job posting has been open for 6+ months (unrealistic expectations or disorganized hiring)
Vague job descriptions with unrealistic requirements ("junior role requiring 10 years experience")
"We're a family" language (often means poor boundaries and emotional manipulation)
"Fast-paced environment" often means chaotic or understaffed
Hiring process red flags:
Excessive interview rounds (7+ rounds is unreasonable)
Unpaid "trial projects" that are actual work they could use
Ghosting between stages
Pressure to accept quickly without time to consider
Unwillingness to discuss compensation range until final stages (wasting everyone's time)
Disrespectful or unprepared interviewers
Role red flags:
Responsibilities don't match the title/level (senior work at junior pay)
"Wearing many hats" that really means "doing three jobs for one salary"
Unclear success metrics or constantly changing priorities
No mention of team, resources, or support structure
Replacing someone who "moved on to other opportunities" (ask why they left)
Job requirements include every technology ever invented (unrealistic expectations)
Green Flags to Look For
Company stability:
Profitable or strong funding runway (2+ years minimum)
Growing team intentionally (not just backfilling constant turnover)
Clear business model and diverse revenue streams
Positive industry trajectory
Strong, stable leadership with clear vision
Transparent about challenges and how they're addressing them
Culture indicators:
Specific values with concrete examples of how they're lived
Employee tenure (people stay 3+ years)
Clear career development paths with examples
Strong benefits and genuine work-life balance policies (ask for specifics)
Transparent communication about company direction
Diverse leadership and genuine DEI efforts (not just lip service)
Role indicators:
Clear expectations and measurable success metrics
Reasonable scope for the level
Supportive team structure (who will mentor you? who will you work with?)
Adequate resources, tools, and budget
Defined growth opportunities
Team is involved in hiring process (good sign they value culture fit)
Questions to Ask During Research (Before You Even Apply)
Does this company's mission align with my values?
Do they have the financial stability to still exist in 12 months?
What's their reputation in the industry?
Do they have a track record of developing people or do they churn and burn?
What are employees saying on Glassdoor, Blind, and other platforms?
Who's on their leadership team? What's their track record?
What's their approach to layoffs and restructures?
The Interview: Evaluating Them While They Evaluate You
Remember: interviews are two-way evaluations. Yes, they're deciding if they want you. But you're also deciding if you want them. In an oversaturated market, it's easy to forget you still have power in this process.
Use the Interview Questions Guide from the Opportunity Evaluation Kit to systematically gather information about whether this role aligns with your priorities.
Questions to Ask (Based on Your Priorities)
If work-life balance is a priority:
"What does a typical week look like in this role? Walk me through a recent week."
"How does the team handle after-hours work or emergencies? When was the last time someone had to work a weekend?"
"What's the PTO policy, and do people actually use it? When was the last time you took a vacation?"
"How does the company support boundaries between work and personal time?"
If growth is a priority:
"What does professional development look like here? What budget or time is allocated?"
"Can you share a specific example of someone who grew in this role? What path did they take?"
"What would success look like in the first 90 days, 6 months, year? How is it measured?"
"What's the typical career progression for this role? Can you show me examples?"
If stability is a priority (crucial in 2025):
"How has the team weathered recent industry changes and market conditions?"
"Can you share the company's approach to financial planning and runway?" (You can ask this professionally)
"How does leadership prioritize this role/team when making budget decisions?"
"What's the average tenure on the team? How many people have joined in the last year vs. left?"
If impact is a priority:
"Can you walk me through how this role contributes to the company's mission with a concrete example?"
"What impact has this role had historically? Can you quantify it?"
"How do you measure success beyond technical metrics?"
"What would 'making a difference' look like in this role specifically?"
If culture fit is a priority:
"How would you describe the team culture? Can you give me a specific example?"
"Can you give me an example of how the team handled a significant conflict or setback?"
"What do people love about working here? What do they consistently find challenging?"
"How does leadership communicate changes or difficult decisions? Walk me through a recent example."
For conference attendees (especially GHC):
"I'm particularly interested in [company's] commitment to [diversity/mentorship/whatever they emphasized at the conference]. Can you share specific examples of how that plays out on this team?"
"At [conference], I heard about [specific initiative]. How does that impact day-to-day work on this team?"
Red Flags in Interviews
Vague or evasive answers to direct questions
Interviewer seems burned out, disengaged, or unhappy
No one can articulate the company vision or how your role contributes
Conflicting information from different interviewers (red flag about internal communication)
Pressure tactics or artificial urgency ("we need an answer by EOD")
Defensiveness about questions, especially about culture or work-life balance
No one seems genuinely excited about the work
Interviews feel disorganized or interviewers are unprepared
They can't tell you why the previous person left
Every answer is about how "fast-paced" and "challenging" it is (code for understaffed)
Green Flags in Interviews
Thoughtful, specific answers with concrete examples
Interviewers are engaged, enthusiastic, and seem happy
They ask about YOUR priorities and genuinely try to address them
Consistent messaging across all interviewers
They respect your time and process
They provide clear transparency on next steps and timeline
You feel energized and excited, not drained or anxious, after interviews
They acknowledge challenges honestly while explaining how they're addressed
The team is involved in the process (shows they value culture fit)
They ask thoughtful questions that show they reviewed your background
Making the Decision: The Trade-Off Framework
You've applied, interviewed, and received an offer (or multiple offers). Now you need to decide. In a competitive market, it's easy to feel pressured to accept immediately. Don't.
Use the Decision-Making Framework from the Opportunity Evaluation Kit.
The Evaluation Process
Step 1: Score against your priorities
Take your prioritized list from Part 1 and score the opportunity:
Non-negotiables: Must be "Yes" or you walk away
Top priorities (1-5): Score 1-5 on how well the role meets each
Secondary priorities (6-10): Score 1-5 on how well the role meets each
Nice-to-haves: Note if present, but don't weight heavily
Step 2: Calculate your alignment score
Weight your priorities:
Non-negotiables: Binary (Yes/No)
Top priorities: 3x weight
Secondary priorities: 2x weight
Nice-to-haves: 1x weight
Example: If "Continuous learning" is priority #4 and you score the role a 4/5: 4 × 3 = 12 points
Add up all your weighted scores for a total alignment score.
Step 3: Consider your current zone
Desperation Zone: An alignment score of 30-40% might be acceptable if it meets all non-negotiables and pays your bills. You're buying time to find something better.
Selective Pressure Zone: Aim for 50-60% alignment. You want a role that moves you forward, not sideways.
Strategic Position Zone (where I am): Hold out for 70%+ alignment. You can afford to wait for a strong fit. I'm not considering anything below this threshold right now.
Step 4: Evaluate the trajectory, not just the current state
Sometimes a role that's 50% aligned today could become 70% aligned in a year if:
You'll learn critical skills that position you for your next move
You'll build valuable relationships with people who can open doors
The company is growing (creating more opportunities)
You'll have leverage to negotiate changes once you prove your value
It positions you to pivot into a different role internally
Ask yourself: Does this role move me toward my dream career, even if it's not aligned with everything I want right now?
When to Say Yes
Say yes when:
All non-negotiables are met (never compromise on these)
The alignment score matches or exceeds your current zone threshold
The trajectory is positive (growth, learning, building toward your goals)
Your gut says this is right (don't ignore intuition)
The trade-offs are conscious and acceptable to you
You can see yourself staying 12-18 months minimum
When to Say No
Say no when:
Any non-negotiable is violated (even in Desperation Zone, some things are non-negotiable)
Red flags significantly outweigh green flags
The role actively moves you away from your career goals
You have a better option available
Your gut is screaming no (even if you can't articulate exactly why)
The culture feels toxic in interviews
You can't see yourself staying even 6 months
My current approach: I'm saying no to anything that isn't at least 70% aligned with my priorities. I have the financial cushion to be this selective. If you're in a different zone, your threshold will be different—and that's completely valid strategy.
When to Negotiate
Always. Even in a tough market flooded with qualified candidates, there's almost always room for negotiation.
Negotiate when:
The offer is close but missing 1-2 key priorities
Salary is below your target (even if other aspects are strong)
You have competing offers or other options
You have unique value to offer that justifies the ask
Something in the offer doesn't meet your non-negotiables
What to negotiate:
Salary (obviously, but know your market rate with current competition)
Remote/hybrid flexibility (huge for many people)
Start date (to finish current projects, take a break, or give yourself transition time)
Title (if it impacts future opportunities or seems mismatched to responsibilities)
Equity (if applicable, and understand vesting schedules)
Sign-on bonus (easier to negotiate than base salary sometimes)
Learning/development budget
Flexible hours
Additional PTO
Guaranteed first review timeline
How to negotiate:
Be direct but collaborative: "I'm excited about this role and I'd like to make it work. To do that, I'd need [X]."
Provide reasoning: "Based on market rates, my experience, and the current competition for talent..."
Bundle requests: "If salary is fixed, could we discuss [remote flexibility/sign-on bonus/additional PTO]?"
Be prepared to walk away if they won't meet your non-negotiables (but only if you genuinely mean it)
Know your BATNA (Best Alternative To a Negotiated Agreement)
The "Good Enough for Now" Strategy
Some people need to take a job that isn't quite right because they need income. That's not failure—it's strategy. Here's how to make it work:
1. Go in with eyes open
Know exactly which priorities you're compromising on
Set a mental timeline (12-18 months typically)
Clearly identify what you'll learn or gain that positions you for the next move
Have an exit plan before you even start
2. Make the most of it
Learn everything you possibly can
Build relationships that will matter later in your career
Document your achievements meticulously for your next job search
Keep your skills current (side projects, online learning)
Network intentionally both inside and outside the company
3. Don't stop preparing for the next move
Keep your resume updated with new accomplishments
Maintain your professional network actively
Stay alert to better opportunities
Continue growing your skills
Set up job alerts for roles that would be great fits
4. Know when to leave
You've learned what you came to learn
Better opportunities emerge that meet more priorities
The role is actively harming you (burnout, toxicity, skills atrophy)
You've hit your timeline
Your financial situation has improved enough to be more selective
A "good enough for now" role is a stepping stone, not a dead end—as long as you treat it strategically and don't get complacent.
Special Note for Different Career Stages
Early career (0-3 years experience): Your priorities might emphasize learning, mentorship, and skill-building over compensation. That's smart. These early roles set your trajectory. Choose companies where you'll grow, even if they don't pay the most.
Mid-career (4-10 years experience): You likely have more leverage and clearer priorities. Don't undersell yourself. In a flooded market, your specific experience matters. Emphasize what makes you unique.
Senior+ (10+ years experience): You're competing with those laid-off Amazon seniors. Differentiate on leadership, vision, and culture-building, not just technical skills. Companies hiring at this level want specific expertise and strategic thinking.
Career changers: Your unique background is an asset, not a liability. Many companies want people who think differently. Emphasize transferable skills and fresh perspective.
The Reality of Building a Dream Career in 2025
Let me be transparent about what I'm doing right now, one week after my contract ended:
I'm not desperately applying to everything. I'm strategically evaluating a small number of excellent opportunities. I'm leveraging my network. I'm being very selective because I can afford to be.
But I'm also realistic. If six months from now I haven't found the right fit, my strategy will shift. My zone might change. My willingness to compromise might increase.
And that's okay. Because I'm not looking for a dream job—I'm building a dream career. The trajectory matters more than any single role.
If you're in the Desperation Zone right now, taking any job that meets your non-negotiables isn't settling—it's being smart about survival. If you're in the Strategic Position Zone like me, using that privilege wisely means being selective about what you say yes to.
The dream career isn't about every role being perfect. It's about making strategic decisions at each step that align with where you are and where you're going.
Your Action Plan
Here's what to do in the next two weeks:
Week 1: Set up your systems
Download and complete the Company Research Template for 5-10 target companies
Set up job alerts for roles matching your non-negotiables
Identify 15-20 people to reach out to for informational interviews
Update your LinkedIn to reflect what you're looking for (without seeming desperate)
Prepare your materials (resume, portfolio, pitch) based on your priorities
If attending GHC or similar conference: Research companies attending and prepare your strategy
Week 2: Research and outreach
Deep dive on 5 companies using your research template
Send 10 networking messages
Apply to roles based on your zone:
Desperation Zone: Apply broadly to anything meeting non-negotiables
Selective Pressure Zone: 5-10 applications to Tier 1-2 opportunities
Strategic Position Zone: 2-5 applications to only Tier 1 opportunities
Ongoing: Stay strategic
Use the Job Evaluation Scorecard for every serious opportunity
Use the Interview Questions Guide for every interview
Use the Decision Framework for every offer
Track what you're learning about what you want
Adjust your strategy based on results and changing circumstances
What's Next
In Part 3 of this series, we'll tackle the hardest part: positioning yourself to actually GET these opportunities in an oversaturated market. We'll cover:
How to craft applications that stand out among hundreds of qualified candidates
How to leverage your unique background and experience
How to interview when you're competing with people from big tech companies
How to build and activate your network without feeling inauthentic
How to maintain confidence when facing rejection repeatedly
But for now, focus on finding opportunities worth pursuing. Use your priorities framework. Be strategic based on your zone. Remember that your dream career is built from many strategic decisions, not one perfect job.
And know that wherever you are in your journey—whether you need any job now or can wait for the perfect fit—you're making choices. Those choices matter. Make them consciously.
📥 Get Your Evaluation Tools
Interview Questions Guide (including GHC-specific approaches)
Opportunity Tracker Spreadsheet
No signup required. Use these for every opportunity you're considering.
Where are you in your job search right now? What's been your biggest challenge in finding roles that align with your priorities? I'd love to hear your experience—especially from GHC attendees and others navigating this flooded market. Connect with me on LinkedIn or follow @code_with_kate where I'll be sharing my own strategic job search journey.
Coming up in Part 3: "Standing Out When Everyone is Qualified: How to Actually Get the Opportunities You Want" - where we'll cover applications, interviews, and maintaining your sanity in a brutal market.
