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Future of Business w/ Delaney William · Aug 19, 2026

Is your career making you depressed? (here’s how to know)

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Delaney William · Future of Business w/ Delaney William

A lot of people assume feeling drained by work is just part of being an adult.

Sunday anxiety. Monday dread. Counting down to Friday…

Getting home with nothing left for your partner, your friends, your health, or yourself.

We normalize it because everyone around us seems to feel the same way.

But what if the problem isn’t your motivation, discipline, morning routine, or ability to handle stress?

What if your career is genuinely making your life worse?

I recently sat down with Dr. Katherine Kirkinis, a psychologist and founder of Wanderlust Careers, a vocational psychology firm that helps people figure out what they actually want to do with their lives and then build a career around it.

Her core belief is simple:

Career is a mental health issue.

And after our conversation, I think a lot more people need to hear that.

(You can watch the full interview, or if you’d prefer, read the ~4 minute summary that follows).

Here were my biggest takeaways.

One of the most important points Katherine made was that when someone is deeply unhappy with their career, the consequences rarely stay contained between 9 and 5.

They come home exhausted.

They have less energy for their spouse or kids.

They stop seeing friends.

Exercise becomes harder.

Hobbies disappear.

They spend Sunday thinking about Monday.

And eventually their entire life gets organized around recovering from work and preparing to go back to it.

This is where I think people can easily misdiagnose the problem.

  • Maybe you’re constantly tired, so you try to optimize your sleep.

  • Maybe you’re irritable, so you work on stress management.

  • Maybe you feel disconnected from your partner, so you focus on the relationship.

  • Maybe you’re unmotivated, so you buy another productivity book.

All of those things can help.

But there is a bigger question worth asking:

What is consuming the majority of your waking life?

If you spend 40, 50, or 60 hours every week doing something that drains you, conflicts with your values, or forces you into a lifestyle you don’t want, you can’t assume the effects disappear when you close your laptop.

I don’t think hating a random Tuesday means you need to quit your job.

  • Every career has stress.

  • Every job has boring work.

  • Every company has annoying people.

The better question is whether the pattern of your career is consistently making the rest of your life worse.

A few questions I would ask yourself:

Do you regularly have nothing left after work?

If your career consistently consumes the energy you would otherwise give to your relationships, health, hobbies, or family, that’s information.

Are you living for weekends and vacations?

There is a difference between looking forward to a vacation and feeling like the only enjoyable parts of your life happen when you aren’t working.

Does the actual work conflict with what you care about?

Katherine has worked with people who weren’t only tired. They felt uncomfortable with what they were helping create. One client, for example, was working on AI systems they didn’t feel good about contributing to.

Has your life changed while your career hasn’t?

The job that was perfect for you at 24 might be completely wrong at 34.

  • Maybe travel used to sound exciting and now you want to be home with your family.

  • Maybe maximizing income used to matter most and now autonomy matters more.

  • Maybe you loved an intense environment until you spent ten years in one.

Our values change.
Our careers need permission to change with them.

And finally:

If you could make the same amount of money doing something else, would you still choose what you’re doing?

That question can uncover a lot.

This was probably the most fascinating part of our conversation.

Katherine works with mid-career professionals who come to her miserable and confused about what they should do instead.

When they trace their career backward, she said it very often ends up back at college.

Why did you choose that major?

“I don’t know.”

Why did you take that first internship?

“It was available.”

Why did you take your first job?

“They were the first company that hired me.”

Then something interesting happens.

Your first job becomes experience.

That experience qualifies you for your second job.

Your second job qualifies you for your third.

Ten years later, you can become highly successful in a career that began with a decision you barely remember making.

There are also deeper forces at work.

  • Maybe everyone in your family was a lawyer.

  • Maybe nobody in your family went to college.

  • Maybe your parents valued stability above everything.

  • Maybe you grew up watching adults treat work as something you’re simply supposed to endure.

Katherine sees both sides of this. Our perception of what’s possible is heavily influenced by the people around us.

You can inherit assumptions like:

  • “Work isn’t supposed to be enjoyable.”

  • “People like me don’t do that.”

  • “I make too much money to change now.”

  • “I already spent ten years building this career.”

  • “This is just what adulthood feels like.”

Those beliefs can quietly become your life.

Most career assessments focus heavily on interests.

Do you like numbers?

Do you like helping people?

Do you like being creative?

Cool. Apparently you’re a farmer.

Katherine’s approach is much more holistic.

Career fit involves your interests, skills, education, personality, values, financial goals, desired lifestyle, and practical circumstances.

An introvert might be perfectly capable of becoming a great salesperson while also finding the work incredibly draining.

Someone might love an industry but hate the lifestyle required to succeed in it.

Someone else might enjoy creative work but also care deeply about earning $200,000 per year.

You have to design around the whole person.

That’s why I think a powerful career exercise is to stop asking:

“What job would I enjoy?”

And start asking:

“What do I want my life to look like, and what career supports that life?”

That is a much better question.

This matters especially if you’re ten or twenty years into your career.

Realizing you’re on the wrong path does not mean quitting tomorrow, taking a massive pay cut, and starting over as an intern.

Katherine actually recommends the opposite:

Thinking in pivots.

One client had spent years as a personal trainer. He loved fitness, but the physical work, nights, weekends, and income ceiling no longer matched the life he wanted.

He eventually became interested in technology.

Instead of trying to erase his entire background and compete directly for unrelated tech jobs, they looked for a bridge.

Fitness → technology inside a fitness company → eventually technology in another industry.

Each move gets you closer.

You can do the same thing across functions.

Sales → marketing.

Operations → product.

Content creation → content strategy.

Traditional execution → AI-enabled strategy.

You don’t have to abandon the last ten years.

You have to figure out how to repackage the valuable parts of those ten years for where you want to go next.

That also changes how you should think about your resume.

Most people build a resume explaining their past.

Katherine sometimes asks clients to write their dream future resume instead.

Write the bullets you wish you could put on your resume one year from now.

Then ask:

  • What experience would I need to make these bullets true?

  • What projects could I volunteer for?

  • What skill could I learn?

  • What responsibility could I take on?

  • What adjacent role would move me closer?

Now you have a roadmap.

Katherine is already seeing clients whose previous jobs have been materially affected by AI.

One example she shared was a photo editor whose previous work could increasingly be completed by software.

Her advice wasn’t to throw away his experience.

It was to figure out how that expertise could move up the value chain.

  • How do you become the person using AI?

  • How do you move from execution into strategy?

  • What adjacent role values the knowledge you’ve already accumulated?

And perhaps most importantly:

Can you build an identity around being adaptable instead of around having one specific job?

I think that’s one of the most valuable career skills anyone can develop right now.

Nobody knows exactly what the labor market looks like ten years from now.

There will probably be jobs that disappear.

There will also be jobs that don’t exist yet.

If your identity is:

“I am a photo editor.”

Disruption can feel existential.

If your identity becomes:

“I am someone who learns quickly, adapts, and finds valuable problems to solve.”

You have a much larger playing field.

You don’t need to love every second of your job.

I don’t think that’s realistic.

But I also don’t buy the idea that you’re supposed to sacrifice most of your waking life to something that consistently makes you miserable.

  • Your career affects your health.

  • Your relationships.

  • Your identity.

  • Your finances.

  • Where you live.

  • How you spend your time.

  • The people you meet.

  • The energy you have left for the people you love.

It’s simply too large a piece of life to leave on autopilot.

So if you’ve been trying to fix everything around your job for years, it might be worth asking one uncomfortable question:

Is the job itself the thing that needs to change?

If this article hit a little too close to home and you want hands-on support exploring these questions, Dr. Katherine Kirkinis and the team at Wanderlust Careers can help.

Their work goes deeper than standard career coaching. They use psychological assessments to evaluate things like your interests, personality, values, skills, lifestyle goals, and other factors that influence career fit, then help you turn those insights into an actual career direction and transition plan.

So if you’re thinking:

“I know something needs to change, but I genuinely don’t know what I should be doing instead.”

This is exactly the type of problem they work on.

Explore Wanderlust Careers: wanderlustcareers.com/contact

If your issue isn’t figuring out what career you want and you’re simply struggling to land the right remote job, that’s exactly what Delaney & team have built Scale Your Salary to solve.

We help qualified professionals execute a done-for-you job search designed to get them into a high-paying remote role, backed by our 90-day placement guarantee for qualified candidates.

apply here: elevatedtech.us

To live, love & robots,

Delaney William

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