Stop Calling It the Messy Middle: 3 Ways to Own It Instead

Stop Calling It the Messy Middle: 3 Ways to Own It Instead

Everyone talks about the "messy middle." That period of time where you're navigating the uncomfortable and the uncertainty. I've been hearing that term more often as I speak to others similar to me who are experiencing a layoff or a career break – or even those who are simply trying to figure out what's next. "Messy" is often used lovingly, but even then it still feels like a negative way to...

read more
Career Authorship: 5 Ways to Take Control of Your Career Story

Career Authorship: 5 Ways to Take Control of Your Career Story

The career infrastructure most of us relied on is gone. For decades, the corporate sector had a built-in narrative structure. You joined a company, climbed a defined ladder, accumulated titles and tenure, and your career told a coherent story almost automatically. The company did the positioning work and your credentials filled in the rest. That structure has largely dissolved. We're living...

read more
How to Build a Portfolio Career: 5 Steps to Diversify Your Income and Boost Your Career

How to Build a Portfolio Career: 5 Steps to Diversify Your Income and Boost Your Career

More professionals are realizing that climbing the corporate ladder isn’t the only path to a fulfilling career. Many are exploring portfolio careers, mixing a full-time role with consulting, freelancing, or a side business. Whether you’re curious about starting something of your own or already have a side hustle that’s not fully realized, a portfolio approach can diversify your income, expand...

read more
Laid Off After 11 Years: Navigating the Next Chapter

Laid Off After 11 Years: Navigating the Next Chapter

The day started like any other Monday. Adam and I were getting James ready for school, making breakfast, easing into the week. Before the hustle and bustle of the morning began, I glanced at my work calendar for the day ahead. There it was. A 9:30am meeting titled “Sync – Kelly & Justin” with the description: “Hi Kelly. Sorry for the late notice but please prioritize this call.” I didn’t...

read more
4 Ways to Redefine Career Fulfillment When You’re Job Hugging

4 Ways to Redefine Career Fulfillment When You’re Job Hugging

For many, we’ve been sold a very specific idea of career fulfillment. Find the right role. At the right company. With the right title, manager, and trajectory. And once you do, fulfillment will follow. But if you’ve been paying attention lately (or going through it personally), that narrative feels increasingly out of sync with reality. Economic uncertainty, a volatile job market, ongoing...

read more

Welcome to Lipstick & Ink®, your home for everything career and life inspired. I’m Kelly, a Chicago-based career coach, resume writer, and speaker.

Whether we’re working together on achieving your career aspirations, refreshing your professional documents, or crafting your brand, think of me as your career sidekick who is going to push you to your potential and cheer you on every step of the way.

CATEGORIES