The Mid-Year Career Check In: 6 Questions That Tell You If It's Time to Move On

It's the middle of the year.

Six months ago, you might have had plans, intentions, or vague ideas about what 2026 would look like for your career.

How's that actually going?

If you're like most people, you've been so busy putting out fires and getting through each week that you haven't stopped to ask yourself: Am I still on the right track?

Here's why mid year is the perfect time for a career check in:

You've got six months of data. That's enough to spot patterns, identify what's working and what's draining you, and see whether the career you're building is actually the one you want.

And you've got six months left. That's enough runway to course correct if you need to. Enough time to make a change before another year slips by.

Most people avoid the mid year career review because they're scared of what they'll find.

What if the answer is "this isn't working"? What if you've wasted six months in the wrong place? What if you realise you need to make a big change and you're not ready?

Here's the truth: avoiding the check in doesn't make the problems disappear. It just makes them bigger.

A small course correction today beats a complete career crisis in six months.

Let me show you how to do a mid year career check in that actually tells you something useful.

Why Most Career Reflection Questions Are Useless

You've probably done a performance review or a personal development plan at work.

They ask questions like:

• "What did you learn this quarter?"

• "What are you grateful for?"

• "What are three wins you're proud of?"

These questions produce nice answers that look good in a company document but tell you absolutely nothing about whether you're in the right career.

They're designed to make you feel productive and keep you moving in the same direction.

They're not designed to make you question whether the direction is actually right.

A real career self assessment asks harder questions. Questions that might make you uncomfortable. Questions that reveal whether you're building a career that fits you, or just ticking boxes for someone else's definition of success.

Here are the six questions for your mid year career review that will actually tell you something.

Question 1: When Did I Feel Most Like Myself at Work in the First Half of This Year?

This is the most important question in your career check in, and most people never ask it.

Not "What went well?" Not "What am I proud of?"

When did you feel like YOU?

When were you energised, not just productive? When did time pass quickly because you were genuinely engaged? When did you leave work feeling fulfilled rather than drained?

Why this question matters for your mid year career review:

The moments when you feel most like yourself reveal where your strengths, values, and interests align with your work.

If you can identify WHAT you were doing in those moments, you've got a roadmap for what to do more of.

How to answer this:

Think back over the past six months. Write down 3 to 5 specific moments when you felt energised and engaged.

Examples:

"I felt most like myself when I was solving that complex client problem independently in March"

"I felt energised when I was presenting the Q2 strategy to the leadership team"

"I felt like myself when I was mentoring the new team member through their first project"

"I felt engaged when I was redesigning that broken process that everyone had been complaining about"

Now look for the pattern:

What were you DOING in those moments?

• Working independently or collaboratively?

• Solving problems or executing plans?

• Leading people or being the expert?

• Creating something new or improving something existing?

• Strategic thinking or hands on work?

This tells you what kind of work actually fits you.

Real example from a client's mid year career check in:

Sarah listed five moments she felt most like herself. Every single one involved either solving complex problems independently or coaching junior team members.

NONE of them involved her actual job responsibilities, which were mostly admin coordination and meeting facilitation.

Her career self assessment revealed: she was in the wrong role. She needed a position with more problem solving and mentoring, less admin.

She pivoted to a project management role six months later. Same company, completely different energy.

Your answer tells you what to do MORE of in the second half of the year.

Question 2: What Drained Me That I Kept Doing Anyway?

This is the question that reveals the gap between what you SHOULD be doing and what you're ACTUALLY doing.

For an honest mid year career review, you need to name what's draining you.

Not just "I'm tired" or "work is stressful." Be specific.

What tasks, meetings, responsibilities, or projects left you feeling empty? And more importantly, WHY did you keep saying yes to them?

Examples of what drains people (from real career check ins):

"I kept volunteering for admin tasks because no one else would do them and I didn't want to let the team down"
→ The real issue: People pleasing is costing you your energy

"I stayed in meetings where my input wasn't needed because I thought showing up made me look committed"
→ The real issue: You're confusing visibility with value

"I kept working on projects I wasn't interested in because they looked good on my CV"
→ The real issue: You're building someone else's version of success, not yours

"I said yes to every request from senior leadership even when I was already overloaded"
→ The real issue: You can't set boundaries with authority

Why this matters in your career self assessment:

The things that drain you aren't random. They reveal patterns about:

• Where your boundaries are weak

• What you're doing out of obligation vs. genuine interest

• Where your role has drifted from what you were hired to do

• What you're tolerating that you shouldn't be

How to answer this for your mid year career check in:

List 5 to 10 things that drained you in the first half of the year.

For each one, ask: Why did I keep doing this?

The "why" is more revealing than the "what."

Your answer tells you what to STOP doing in the second half of the year.

If you keep doing the same draining things for another six months, you'll end the year burnt out and resentful.

Question 3: What Did I Avoid That I Know I Should Have Done?

This question is brutal. But it's essential for an honest mid year career review.

What did you put off in the first half of the year because it felt scary, uncomfortable, or difficult?

The conversation you didn't have. The application you didn't submit. The boundary you didn't set. The feedback you didn't give. The opportunity you didn't take.

Why this matters in your career check in:

The things you avoid reveal your growth edge.

They show you where fear, insecurity, or discomfort is holding you back.

And here's the truth: if you avoided it in the first half of the year, you'll avoid it in the second half too—unless you consciously decide to address it.

Common things people avoid (and what they reveal):

Avoided asking for a raise
→ Growth edge: Building confidence to advocate for your worth

Avoided applying for stretch roles
→ Growth edge: Reframing imposter syndrome and backing yourself

Avoided setting boundaries with your manager
→ Growth edge: Learning to say no without guilt

Avoided the difficult conversation with a underperforming team member
→ Growth edge: Developing uncomfortable leadership skills

Avoided exploring career options outside your current company
→ Growth edge: Facing the fear of change and the unknown

How to use this in your mid year career check in:

Write down one thing you avoided in the first six months.

Then ask: What would need to be true for me to do this in the second half of the year?

Example:

"I avoided applying for senior roles because I didn't think I was ready."

What would need to be true: I'd need to reframe 'ready' as 'capable of learning' instead of 'already perfect'

Action for second half of year: Apply for two stretch roles even if I'm only 70% qualified

Your answer tells you what to work on in the next six months.

The thing you're avoiding is usually the thing you most need to do.

Question 4: If I Could Redo One Career Decision From the First Half of This Year, What Would It Be?

This isn't about regret or self criticism. It's about learning.

In your mid year career review, identify one decision you'd change if you could go back.

Not to beat yourself up. To extract the lesson so you don't repeat the pattern.

Examples from real career self assessments:

"I would have said no to that extra project in February"
→ Lesson: My capacity isn't infinite, and saying yes to everything means doing nothing well

"I would have spoken up in that leadership meeting instead of staying quiet"
→ Lesson: My perspective has value, and staying silent doesn't keep me safe

"I would have left in March instead of giving it 'one more quarter' to see if things improved"
→ Lesson: Trust my gut sooner. If I've been unhappy for six months, three more months won't fix it

"I would have negotiated the job offer instead of accepting the first number"
→ Lesson: I'm allowed to advocate for myself. Negotiation doesn't make me difficult.

How to answer this in your career check in:

Think back over the first six months. What's one decision you made that, in hindsight, wasn't quite right?

Then ask:

1. What would I do differently?

2. What's the deeper pattern here?

3. How do I avoid repeating this in the second half of the year?

Your answer tells you what patterns to interrupt before the year ends.

Question 5: What Am I Tolerating That I Wouldn't Recommend to a Friend?

This is the most revealing question in your mid year career review.

Imagine your best friend came to you with your exact job situation. What would you tell them?

Would you tell them to stay in a role where they're undervalued and underpaid?

Would you tell them to accept behaviour from a manager that crosses boundaries?

Would you tell them to keep waiting for things to get better when nothing's changed in six months?

If the answer is no, why are you staying in it?

This question works because it bypasses your rationalisations.

You can justify almost anything to yourself. "It's not that bad." "It could be worse." "I should be grateful."

But you wouldn't let someone you care about tolerate the same things.

Common things people tolerate (that they'd never recommend to a friend):

• A manager who micromanages, undermines, or takes credit for your work

• Being consistently overworked with no recognition or compensation

• A toxic team culture where gossip, blame, or passive aggression is normalised

• Being passed over for promotions or development opportunities repeatedly

• A role that's grown far beyond its original scope with no title or pay adjustment

• Working in a company whose values fundamentally conflict with yours

How to use this in your career self assessment:

Write down: "If my friend had my job, I would tell them..."

Be brutally honest.

Then ask: If I wouldn't recommend this situation to someone I care about, why am I accepting it for myself?

Your answer tells you what needs to change in the second half of the year.

Question 6: What's the Career Move I'm Not Making Because I'm Scared?

The final question for your mid year career check in is about fear.

Not the move you CAN'T make. The move you're CHOOSING not to make because you're scared.

Examples:

"I'm not applying for senior roles because what if I'm not ready?"

"I'm not pivoting industries because what if I fail?"

"I'm not asking for flexible working because what if they say no?"

"I'm not starting my side business because what if no one wants it?"

"I'm not leaving this job because what if I can't find anything better?"

Here's the truth about fear in your career:

Fear is information. It tells you where growth lives.

The career move you're most scared of is usually the one you most need to make.

Why this question matters in your mid year career review:

Because if you don't name the fear now, you'll still be stuck in the same place in six months.

You'll find another reason to wait. Another excuse. Another "I'll do it when..."

And another year will pass.

How to answer this:

Complete this sentence: "If I weren't scared, I would..."

Then ask:

1. What's the worst that could actually happen?

2. Is the risk of trying worse than the cost of not trying?

3. What would I need to believe about myself to do this anyway?

Your answer tells you what to be brave about in the second half of the year.

How to Actually Use Your Mid Year Career Review Answers

Right, you've worked through the six questions. You've got pages of notes. You've been honest about what's working, what's draining you, and what you're avoiding.

Now what?

Most people do the reflection and then... nothing. They close the notebook and go back to exactly what they were doing before.

Don't do that.

Here's how to turn your career check in into actual change.

Step 1: Categorise Your Answers

Go back through your six question answers and sort them into three buckets:

What worked (first half of year):

• Moments you felt most like yourself

• Things that energised you

• Decisions you're proud of

What didn't work:

• Things that drained you

• What you kept avoiding

• What you're tolerating

What's next (second half of year):

• What to do more of

• What to stop doing

• What to work on

• What patterns to interrupt

• What needs to change

• What to be brave about

Step 2: Find the Patterns

Don't just list answers. Look for THEMES across your responses.

Example pattern from a real mid year career self assessment:

What energised me: Working independently on complex strategic problems

What drained me: Repetitive team meetings where decisions were made by committee

What I avoided: Asking for more autonomy because I didn't want to seem difficult

What I'm tolerating: A micromanaging boss who approves every small decision

The pattern: This person needs a role with more autonomy, less collaboration, and a manager who trusts them.

The career move they're scared of: Applying for senior individual contributor roles instead of management track (because everyone says you should want to manage people)

What they need to do in the second half of the year: Stop trying to fit the "collaborative team player" mould and find a role that actually matches how they work best.

Look for your own patterns.

If the same themes keep appearing across multiple answers, that's not a coincidence. That's your career telling you something.

Step 3: Make ONE Change for the Second Half of the Year

This is the most important step in your mid year career review.

Don't make a list of ten things you want to change. Don't create a vision board. Don't write vague intentions like "work on confidence" or "be more assertive."

Pick ONE specific thing you will do differently in the next six months based on what you learned.

Examples of good "one change" commitments:

"I'm going to say no to one non essential meeting every week to protect my focus time"

"I'm going to apply for two stretch roles even though I'm scared I'm not ready"

"I'm going to have the conversation with my manager about restructuring my role to drop the admin work"

"I'm going to stop volunteering for tasks that aren't in my job description"

"I'm going to block two hours every Friday for strategic thinking instead of firefighting"

Why just one change?

Because one change you actually DO beats ten changes you think about and never implement.

How to make it stick:

1. Write it down: Don't just think it. Write the specific change.

2. Make it measurable: "Set better boundaries" is vague. "Say no to one meeting per week" is measurable.

3. Schedule it: Put it in your calendar. Make it real.

4. Tell someone: Accountability increases follow through.

Your one change becomes your focus for the second half of the year.

The Mid Year Career Check In That Changed Everything

Let me tell you about a client who did this mid year career review last year.

Emma had been a marketing manager for eight years. Good salary. Respected in her company. On paper, everything looked fine.

But she felt stuck.

We did the six question career self assessment in June.

Her answers:

Felt most like herself: When she was writing strategy documents alone, away from the team

What drained her: Endless collaborative brainstorming sessions that never led to decisions

What she avoided: Applying for senior strategy roles because she thought she needed an MBA

What she'd redo: She would have said no to leading the rebrand project (highly visible but not strategic)

What she's tolerating: A role that's 80% team management, 20% strategy (when she was hired to do the opposite)

Career move she's scared of: Pivoting to a pure strategy role and giving up the "safe" management track

The pattern was obvious:

Emma is a strategic thinker who works best independently. She's been forcing herself into a collaborative management role because that's what "career progression" looked like at her company.

Her one change for the second half of the year:

Apply for three senior strategy roles (individual contributor, not management) at different companies.

What happened:

She applied in July. Got interviews in August. Had an offer by September.

She's now a Senior Strategy Lead at a consultancy. Same salary. Half the team management. Double the strategic work.

She told me: "I spent eight years climbing a ladder I didn't even want to be on. That mid year check in was the first time I asked myself if the ladder was against the right wall."

That's the power of an honest career self assessment.

When Your Mid Year Career Review Tells You It's Time to Leave

Sometimes the career check in reveals something you've been avoiding:

This job isn't fixable. It's time to go.

How do you know if you're in a "stay and fix" situation vs. a "pivot and leave" situation?

You should STAY if:

• Most of what drains you is within your control (boundaries, workload, communication)

• The work itself aligns with your values and uses your strengths

• You respect your manager and colleagues

• The problems are specific and fixable

• You can see a path to growth or change

Action: Make the one change. Give it three months. Reassess.

You should PIVOT if:

• The work itself drains you, not just the workload

• You've fundamentally outgrown the role or industry

• Your values don't align with the company's direction

• You're staying out of fear or guilt, not genuine desire

• You've tried to make it work and nothing's changed

• You can't see a future here that excites you

Action: Start building your exit plan. Update your CV. Explore options. Set a timeline.

You should REDESIGN if:

• You like the company and the work, but the current setup isn't working

• The role has grown beyond its original scope

• You'd stay if specific things changed

• You have leverage (strong performance, hard to replace)

• The company values you and would negotiate rather than lose you

Action: Build your case. Schedule the conversation. Advocate for what you need.

Not sure which path you're on?

I created a free decision guide called "Should I Stay or Should I Pivot?" that walks you through exactly how to figure this out. It includes the full Stay/Pivot/Redesign framework with worksheets and action plans. Grab it if you need more than this blog post can give you.

Frequently Asked Questions About Mid Year Career Reviews

How often should I do a career check in?

Quarterly is ideal - that's every three months. It's frequent enough to catch problems early but not so often it feels overwhelming.

At minimum, do a proper mid year career review and an end of year review. That's twice a year.

Mid year is particularly powerful because you've got enough data from the first half to spot patterns, and enough runway in the second half to course correct.

What if my mid year career self assessment reveals I'm completely in the wrong career?

First: that's actually a good thing. Clarity is always better than confusion, even when the clarity is uncomfortable.

Second: you don't have to change everything tomorrow.

Start with one small step:

• Research what else is out there

• Talk to people in fields that interest you

• Identify your transferable skills

• [Read this guide on career change with unrelated experience](link to blog from newsletter #10)

You've got six months left in the year. That's enough time to explore, plan, and potentially make a move. Or to decide you're going to make the move in Q1 next year.

The worst thing you can do is ignore what the career check in revealed and hope it goes away.

What if I don't have time for a two hour career review?

Do a 15 minute version.

Answer just three questions:

1. On a scale of 1-10, how energised am I about my work right now?

2. What's one thing draining me that I could stop doing?

3. What's one career move I'm not making because I'm scared?

Even 15 minutes of honesty is better than six more months of autopilot.

What if my mid year career check in reveals problems but I can't leave right now?

You might not be able to leave immediately for legitimate reasons - financial commitments, visa restrictions, family circumstances, timing.

That doesn't mean you do nothing.

Ask: What CAN I control?

Even if you can't leave:

• You can set better boundaries

• You can start exploring what's next

• You can build new skills

• You can expand your network

• You can stop saying yes to things that drain you

• You can have conversations about restructuring your role

You might not be able to change your situation overnight. But you can start moving in a better direction.

Is it normal to feel stuck or unhappy mid year?

Yes. Completely normal.

Mid year slump is real. The new year energy has worn off. You're not close enough to year end to feel motivated by a fresh start. You're just... in the middle.

That's why the mid year career review is so valuable. It gives you a chance to reset, refocus, and choose how you want the second half of the year to go.

You don't have to wait until January to make changes.

What if I do the career check in and realise I've wasted the first half of the year?

You haven't wasted it. You've learned from it.

Every experience - even the draining ones, the mistakes, the things you avoided - gave you information about what you need and what you don't.

You can't get the first six months back. But you can decide what to do with the next six.

That's the point of the mid year career self assessment. Not to dwell on what's behind you, but to course correct for what's ahead.

Your Next Steps After This Mid Year Career Review

If you've read this far, you're serious about making the second half of the year count.

Here's what to do next:

This Week:

Set aside two hours. Grab a notebook. Work through the six questions:

1. When did I feel most like myself at work in the first half of this year?

2. What drained me that I kept doing anyway?

3. What did I avoid that I know I should have done?

4. If I could redo one career decision from the first six months, what would it be?

5. What am I tolerating that I wouldn't recommend to a friend?

6. What's the career move I'm not making because I'm scared?

Answer them honestly. Not how you think you should answer. How you actually feel.

This Month:

Find the patterns in your answers.

Choose ONE change for the second half of the year.

Schedule it in your calendar. Make it specific. Make it real.

This Quarter:

Review your one change. Is it working? What's shifted?

Schedule your next career check in for three months from now.

Keep adjusting. Small, consistent course corrections beat waiting for a crisis.

Final Thought

You're halfway through the year.

Six months have passed. Six months remain.

You can spend the second half exactly like the first half - going through the motions, tolerating what drains you, avoiding what scares you.

Or you can use this mid year career review to make one intentional change that shifts everything.

The choice is yours.

But whatever you do, don't ignore what this career check in revealed.

Your career is telling you something. The question is: are you listening?

Ready to figure out if you should stay, pivot, or redesign your current role? Download my free "Should I Stay or Should I Pivot?" decision guide. It includes the full framework with worksheets to help you make the call. Stop going in circles. Get clarity.

Want to build a career that actually fits you instead of just ticking boxes? Career Clarity Foundations - Know your Direction walks you through exactly how to identify what you want, build the confidence to go after it, and make the change without starting from scratch.