32 Questions to Ask Your Friends Before You're 40

Your 20s and 30s are a constant state of transition. Careers shift, identities evolve, relationships change, people become parents (or choose not to), financial pressures grow, and the big question, “Am I where I thought I’d be?” looms large. Amid all of this, many women begin to crave more intentional, honest connections with the people in their lives—especially friends.

With age, friendship deepens. The childlike fun and laughter remain, but friendship becomes a space for reflection, vulnerability, and tough conversations. We asked our audience how often they talk to their friends about their careers—things like their trajectory, challenges, dreams, and long-term goals—and what those conversations typically sound like.

Just 44 percent of women say they talk to their friends about their careers often or very often. That means more than half (57 percent) only have those conversations occasionally, if at all. In other words, career talk isn’t happening as frequently as it could be. But when it does happen, it tends to be honest and deeply supportive.

Here’s a glimpse into what women chat about with friends:

• “I talk about my difficulty feeling motivated, frustration with not getting promoted, and feeling disenchanted with corporate life in general. A common theme is the tension between being a parent and an employee.”

• “I have a small but close circle of friends, and when we discuss work, our conversations often revolve around the challenges it entails—such as workplace dynamics, the relationship between employees and the company, and leadership interactions.”

• “Career development podcasts, resume building, salary, benefit packages, positions in each other's fields that we see online, urging each other to explore opportunities. If we didn't have to worry about money, we would open a restaurant etc.”

• “Depends on the friend—if they're in the same field, we talk about the latest free resources and software issues. If they're not in the same field, we usually talk about retirement and if our benefits have changed course with the economy.”

These kinds of conversations matter. You never know what someone else is carrying, or what insight they might offer that shifts your own perspective. And while talking shop is important, your career is just one piece of the puzzle. Friendship also means helping to navigate all the other layers of life: identity, fulfillment, money, family, values, and dreams.

Read more: Compartmentalizing in 2025 Is Possible. Here Are 5 Ways to Work Through (Mostly) Anything

6 meaningful conversation topics to bring up with friends

These aren’t always easy topics to bring up, but they’re often the ones that lead to the most connection. Think of the questions and prompts below as gentle ways to spark reflection, not scripts to follow. Whether you're catching up on a walk, chatting over coffee or wine, or texting in a group chat, what matters most is creating space for honest dialogue. 

1. Career and purpose

Our careers can be deeply tied to our identity, yet we don’t always create space to talk about them honestly with all their highs, lows, pivots, and “what ifs.” Opening up about work with friends can help us feel less alone in the challenges—imposter syndrome, bad bosses, promotions that didn’t happen, or the unspoken desire to start over—and become more excited about future possibilities. Sometimes, it’s the fresh perspective from a friend that sparks a new idea or gives you the encouragement you need to keep going.

Read more: Dealing with Conflict at Work? Here Are 17 Things Your Best Friend Would Tell You To Do

2. Friendship maintenance

Friendships evolve over time, but they shouldn’t fall to the wayside. As life gets busier and responsibilities pile up, it’s easy to forget to check in on the health of the friendships themselves. Taking the time to reflect on what you both need and value in a friendship can deepen the relationship and ensure you're showing up for each other in meaningful ways. If your friend is navigating something big, like new parenthood, sometimes the most powerful question is a simple, “How are you really doing?”

3. Aging, health, and self-image

As we get older, our bodies and minds undergo significant changes. With them, come questions about health, wellness, and how we see ourselves. Often, we don’t talk about these changes until we’re in the thick of it, wondering, wait, is this normal? Whether it’s unexpected hormone shifts, changing relationships with our looks and energy levels, perimenopause, fertility, chronic illness, or confidence, these topics can be confusing. When you open up to your circle, you create a safe space for shared wisdom, support, and validation.

Read more: Are We Moving Beyond Makeup? Let’s Explore the Evolving Perceptions at Work.

4. Money and security

Money is still a taboo subject, but talking about it breaks down barriers and helps you make more informed, empowered decisions. Discussing finances with friends can ease the shame or stress we sometimes carry and lead to unexpected wins, like smarter budgeting ideas, helpful resources, or new ways to navigate financial curveballs. It’s time we chat more casually about retirement plans, splurging on things that bring joy, and managing financial stress.

Read more: A Beginner's Guide to Retirement Plans & Financial Literacy

5. Legacy and values

As you approach milestones like turning 40, you might find yourself reflecting on the broader legacy you’re creating. What kind of life are you building? What values are guiding your choices? What impact do you want to leave behind, big or small? These reflections can feel both inspiring and daunting, which is why they’re worth talking through with friends. Sharing your thoughts on purpose, priorities, and the kind of legacy you want to have can lead to clarity while reminding you that success doesn’t have to look like anyone else’s.

6. Mental health and growth

Adulthood doesn’t come with a user manual, and it’s easy to feel blindsided by the emotional challenges that pop up along the way. Maybe it’s burnout that snuck up on you, anxiety that feels less manageable than it used to, or unlearning beliefs you didn’t even realize you’d been carrying. Sharing these moments with friends can be incredibly validating. It reminds us we’re not the only ones figuring it out as we go, and it opens the door to deeper support, growth, and connection. Sometimes just saying it out loud is the first step forward.

Read more: The Therapy Effect: How Women Are Using Mental Health Support to Thrive at Work