Yesterday I had a powerful conversation with someone navigating a return from entrepreneurship back into employment. But the truth is, everything we spoke about applies to anyone in a period of transition, whether you’re pivoting roles, re-entering the market, or questioning what "good” looks like next.
Change can feel daunting. The market is tougher, companies are selective, and job hunting can drain your energy if you don’t have a clear sense of direction.
Here’s the roadmap I walked her through. It’s the same one I wish I’d had earlier in my own career and is built on the key lessons I’ve learned over 20+ years and over 7 job moves.
1. Start Big: What Gives You Energy?
Before you even look at job boards, take a step back and ask yourself:
- What kind of work lights me up?
- What gives me energy on a day-to-day basis?
- What type of problems do I love solving?
Examples might be:
- Being around people
- Doing mission-aligned work
- Working with customers
- Solving problems using data
- Building processes, products, or partnerships
- Working in environments where curiosity and ownership matter
This step isn’t about job titles. It’s about what makes you feel alive at work.
Let your answers be wide, intuitive, and honest.
2. Identify Your "Ick”: What Drains You?
Just as important is knowing what takes your energy.
Ask yourself:
- What behaviors, environments, or tasks make work feel heavy?
- What patterns have burned me out in previous roles?
Examples include:
- Inconsistent or unclear decision-making
- Authoritarian leadership
- Dysfunctional processes
- A lack of psychological safety
- Cold calling (if you dread it!)
- Work that conflicts with your values
Energy drainers are warning signs of misalignment.
If a role expects you to spend time doing something you actively dislike and will be evaluated on, that’s a red flag.
3. Understand the Company’s Values (Beyond the Poster on the Wall)
Values are only useful if they’re lived.
Large companies often publish Vision / Mission / Values statements, known in corporate jargon as the "Employee Value Proposition”. These can be helpful, if the culture reflects them. Sometimes they’re just glossy words rather than guiding principles.
Smaller companies may not publish them formally, so explore their About Us pages, careers pages, and customer messaging.
Look for signals of a healthy culture:
- Do they talk about learning, growing, improving?
- Do they acknowledge failures as learning moments?
- Do they emphasise their people?
- Do they focus on customer impact and value?
If none of this is present, that’s telling in its own way.
4. Understand the Business: Size, Growth, and Market Position
Not all companies offer the same opportunities for growth.
A few things to look for:
Size & Stage
- Start-up
- Scale-up
- Mid-sized
- Enterprise
Each comes with different expectations, stability, and pace.
Growth Trajectory
This is crucial: a company that isn’t growing will struggle to invest in people.
If growth isn’t obvious from public information, ask directly in interviews:
- "Where is the company heading in the next 12-24 months?”
- "What’s been your growth trajectory recently?”
- "What opportunities or risks do you see?”
Mission Fit
Does their mission excite you?
If their mission is to "optimize the procurement process for logistics companies” and you don’t care about that, it may not be your place.
It’s hard to thrive in a role if you don’t believe in what the company is working towards.
5. Who Do They Serve? (Even if You’re Not Customer Facing)
Understanding a company’s customers shapes everything.
- Do they serve large corporations?
- SMEs?
- Start-ups?
- Specific industries?
Even if you’re in a back-office role, the type of customer influences the culture, the pace, and the expectations.
Ask yourself:
"Do I want to contribute to serving this type of customer?”
If the answer is no, that’s extremely useful information.
6. Position Your Skills Through a Customer-Centric Lens
Think of an employer as your biggest (or only!) customer.
Your job is to help them achieve their goals.
Instead of listing all the things you’ve ever done, ask:
- What does this company care about?
- What skill gaps are they trying to fill?
- How can I tell stories that make my experience relevant?
Even if you haven't held the exact job title, chances are you have many of the underlying skills. Your job is to connect the dots for them.
Look across your entire career:
- What are the transferable skills?
- Where have you solved similar problems?
- What results have you driven that would matter to them?
Craft your language so it speaks directly to their world.
7. Research the People Behind the Job
Culture is lived by people. So, look at:
- The founder(s)
- The CEO
- The hiring manager
- Anyone you’d be working with directly
Check their LinkedIn activity:
- What do they care about?
- What do they share?
- What behaviors do their posts signal?
- Do you see values you respect?
If you have mutual connections, even better! Ask for a warm introduction.
Prepare thoughtful questions:
- "What’s the vision for this team?”
- "What does success look like 6-12 months from now?”
- "What’s a challenge the team is working on improving?”
- "What are some of the blind spots they have spotted and learned from over the past year?”
Their answers tell you far more than any job description will.
8. Don’t Mass-Apply. Be Strategic.
The current market is hard. Sending 200 applications on LinkedIn is a poor strategy that can make you spiral with self-doubt.
Instead:
- Apply only to roles you genuinely care about
- Reach out to the recruiter posting the job and ask for a 15-minute call
- Or find someone in your network who knows someone there
How they respond tells you everything:
- If the recruiter declines a short chat, it’s unlikely any application would get you more than an automatic rejection email. Don’t waste your time there!
- If they take the call, you instantly stand out
This is about quality applications, not quantity.
9. Rethink Your Cover Letter as a Personal Mission Statement
Most cover letters are dull: "Here’s what I’ve done. Here are my skills.”
But employers are also looking for:
- Cultural fit
- Motivations
- Personality
- Alignment with their values
- Evidence you understand their world
Think of it this way:
Your cover letter should connect why you care with why you’re a fit.
Tell a story. Be human. Show why their mission and your strengths are a perfect match.
10. Remember: Interviews Are a Two-Way Evaluation
It’s easy to forget this when you feel pressure to secure a role.
But you’re not just being assessed.
You’re also assessing whether you want to dedicate your energy, time, and talent to this company.
Ask yourself after every conversation:
- Did I feel heard?
- Did they value curiosity and questions?
- Did they respect my experience?
- Did I feel energized or drained?
And if something feels "off,” it’s okay to walk away.
The right role isn’t just about what you can do, it’s about where you can thrive.
Final Thought
In a tough market, it’s tempting to take any opportunity that comes your way. But you spend far too much of your life at work to simply settle.
Be intentional.
Be curious.
Do your due diligence.
And trust that alignment, between values, mission, energy, and people, is what ultimately drives long-term career success.
Your next chapter deserves that level of care.
