I’ve been thinking about the people we turn to when we don’t know what comes next. Early in our careers, asking for help feels pretty natural. We’re new, we’re learning, and nobody expects us to have all the answers. Then we build experience, earn credibility, and become the person everyone else calls for advice. Somewhere along the way, we start believing we should be able to figure out our own careers without help. That belief can keep us stuck longer than we’d like to admit.

I think mentors may matter even more at midcareer. You may know how to do your job beautifully and still need help deciding whether you want to keep doing it. You may be ready for a leadership role but are unsure how to be considered for the right opportunity. Or you may have a career that looks terrific from the outside but feels increasingly uncomfortable from the inside. Those are good reasons to seek perspective, even if you’re usually the one providing it.

Your questions have become strategic

Early in your career, you’re often focused on learning the work and establishing yourself. How do you handle a difficult client? What does your boss expect? Which assignments will help you grow? A mentor can explain the unwritten rules, give you useful context, and help you avoid mistakes you may not anticipate. Having someone you can ask, “Is this normal?” can save you considerable time and frustration.

At midcareer, the questions get more complicated because the decisions involve more than your next promotion. Do you actually want partnership? Would moving in-house give you the work and flexibility you’re looking for? Are you interested in managing people, or do you feel pressured to pursue management because it’s the next available step or it’s what you ‘should’ do? Add children, aging parents, health concerns, or financial responsibilities, and suddenly “What should I do next?” has quite a few moving parts.

Consider an attorney who’s spent years working toward partnership and is finally being considered. Everyone offers congratulations, but she’s wondering whether she wants the business development expectations, administrative responsibilities, and schedule that come with it. A useful mentoring conversation would help her examine the actual job, including what she’d gain and what she’d give up.

Before you ask someone for advice, write down the decision you’re trying to make. “I’m unhappy at work” is a starting point, but “I want more control over my schedule, and I’m trying to decide whether that’s possible here” gives you something concrete to discuss. The clearer you can be about what’s bothering you, the more useful any mentoring conversations will be.

Working harder isn’t the answer

High achievers tend to have a familiar response when things feel uncertain: work harder. Take another assignment, become more responsive, and demonstrate just how valuable you are. That approach probably helped you build your reputation. It may also be the reason you’re now carrying responsibilities that leave very little room to consider what you want.

Suppose you want a leadership role, but you’re so dependable that everyone keeps giving you work that needs immediate attention. You complete it, receive appreciative emails, and get more of the same. Meanwhile, someone else gets the opportunity to lead a strategic initiative. Before you volunteer for another urgent project, you need to understand which experiences will help you move toward leadership and how to seek those specific opportunities.

A mentor can help you examine that pattern. They might ask whether you’ve told anyone what you want, whether the work you’re accepting supports that goal, and what you could delegate or decline. Those questions can be difficult, especially if being helpful is part of your professional identity. They can also reveal a practical next step that another late night at your desk wouldn’t have generated.

Good work needs to be known

Doing excellent work gives people a reason to trust you. As you move through your career, you also need relationships with people who understand your capabilities and know where you want to go. If you’re interested in leading a team, building a practice, or serving on a board, people who make or influence those decisions need to know that. Waiting for others to recognize your ambitions without being told can lead to a very long wait.

This is where it helps to understand the difference between a mentor and a sponsor. A mentor shares experience, asks questions, and helps you think through decisions. A sponsor uses their influence to advocate for you. They might recommend you for an assignment, introduce you to a decision maker, or suggest your name when an opportunity comes up. Although one person can play both roles, you shouldn’t assume that every mentoring relationship includes advocacy.

When I realized that I would thrive in a position closer to the deal making (sales) rather than the deal papering (lawyering), I shared my thoughts about searching for a non-lawyer role with one of my mentors, Joe Miller, who was the senior vice president of product development at SEGA. He said to me, “I’d rather have you come work for me than leave the company.” And with that, he moved from being my mentor to becoming my sponsor, advocating for me among the other executives, including my boss. Joe never would have known to do that if I hadn’t shared my interest in moving to the business side.

Make your interests specific enough that someone can act on them. Instead of saying, “I’d like to do something more strategic,” try, “I’d like to lead a project involving our client service process. I’ve handled several recurring problems, and I have ideas about how we could prevent them.” By being more specific, you’ve given the other person context, a direction, relevant experience, and a reason to remember you when the right conversation happens.

Giving advice while needing it

Being experienced doesn’t make every decision easier. Sometimes it makes asking for help harder because it feels like other people assume you’ve already figured everything out. You may be supervising employees, advising clients, or leading a committee while privately wondering whether you’re spending your time on the right things. Having people depend on you doesn’t eliminate your own need for a sounding board.

Choose someone who can listen without needing you to stay exactly where you are. A colleague who relies on you may have valuable insight, but they may also have a strong preference to keep you in your current role. Someone outside your immediate team can offer a different perspective. You want room to say, “I’m good at this, but I’m not sure I want to keep doing it,” and explore that honestly.

During a walk with one of my favorite mentors, Denise asked me why I was staying in a particular job when she would have been out of there after a year. Her question gave me pause. I really had to take a moment and reflect on the reasons I was subjecting myself to such an unhealthy work environment.

Pay attention to how a potential mentor responds when you disagree or describe something difficult. Can they ask questions before offering solutions? Can they acknowledge that your priorities might differ from theirs? Experience is useful, as is curiosity. Someone who insists you follow their path may have plenty to teach you about that path but may not be helpful beyond that.

Fortunately, Denise and I talked through my situation, and I stated that fundamentally, I had autonomy and was five minutes from my kids’ school and our home, which she acknowledged were both important at that stage of my career and life.  

Build a constellation of support

You don’t need one person to serve as your mentor, sponsor, coach, industry expert, and emergency career hotline. Different questions call for different people. Someone who understands your organization can help you navigate an internal opportunity. Someone who’s changed careers can help you consider or manage a transition. A trusted peer may understand your daily challenges better than others.

Start by looking at the relationships you already have. Who helps you see possibilities? Who gives you candid feedback? Who knows people you’d like to learn from? Then look for gaps. If everyone you talk to works in your organization, you may need an outside perspective. If your conversations focus entirely on getting promoted, you may need someone who’ll also ask whether the promotion fits your life.

When I was in law school, my mom was part of MIT/Stanford Venture Lab and occasionally they would hold meetings at our house, which gave me the opportunity to meet people across the entrepreneurial spectrum. Later when I joined a startup, I contacted a few of them for informational interviews to learn more about venture funding models and investment structures. These conversations broadened my perspective and gave me foundational information to help me succeed in my new role.   

Your support system doesn’t have to consist of people who are older or more senior. A younger colleague may help you understand a new tool or changing client expectations. A peer may share an approach to managing a team that you haven’t tried. Someone in another profession may ask a question that exposes an assumption everyone in your field takes for granted. Useful perspective can come from several directions.

Make a specific, manageable ask

“Will you be my mentor?” can feel like a large request because it leaves so much undefined. The other person doesn’t know whether you’re asking for one conversation, monthly meetings, or ongoing availability whenever something comes up. Start with a question they can reasonably help you answer and a request that respects their time. You can build the relationship from there.

For example, you might say, “I’m considering my first management role, and I’d appreciate your perspective on what you wish you’d understood before making that transition. Would you have 15 minutes for a conversation in the next few weeks?” That tells them why you’re reaching out, what you want to discuss, and how much time you’re requesting. It also gives you a clear reason to prepare.

Bring two or three thoughtful questions and enough context to make them useful. If you’re considering a move in-house, ask about the daily work, how success is measured, and what surprised them after they transitioned to an in-house role. You don’t need to deliver your entire career history before asking your first question. Give them the relevant background, listen carefully, and leave room for the conversation to develop.

If the conversation is helpful, ask whether they’d be open to hearing how things go or talking again after you’ve taken your next step. As the relationship develops, agree on what works for both of you, including how often to connect and what you’ll discuss. You don’t need a formal arrangement, but clear expectations help you build a relationship that respects everyone’s time.

Follow through and close the loop

Follow-through is one of the easiest ways to stand out. If someone suggests a resource, look at it. If they make an introduction, respond promptly and come prepared. If they help you identify an action, take it or decide thoughtfully why you won’t. Then close the loop and let them know what happened. The extra mile is never crowded.

A useful follow-up might sound like this: “Your suggestion helped me realize I hadn’t asked what the role would involve day to day. I spoke with the department head, and we discussed expectations and staffing. I’m still considering it, but I have much better information now.” You’ve shown that you valued the conversation and used it to move your decision forward.

You don’t have to take every piece of advice you receive. Your mentor brings experience and perspective; you bring knowledge of your own priorities and circumstances. If you choose a different direction, you can explain what you learned and why you made that choice. A healthy mentoring relationship leaves room for your judgment, including decisions your mentor wouldn’t make for themselves.

Use advice to make a practical decision

Mentoring becomes useful when the conversation changes what you understand or what you do. Afterward, take a few minutes to write down what stood out. Did you discover that you need more information? Did someone challenge an assumption you’ve been treating as fact? Did you realize you’re pursuing an opportunity because it’s available, rather than because you want it? Choose one action that follows from that insight.

That action can be small. You might schedule a conversation with someone doing the job you’re considering, ask how candidates are selected for leadership assignments, or review your calendar to see which commitments are crowding out your goals. Give yourself a date to complete it. “I’ll explore my options” is easy to postpone; “I’ll contact two people by Friday” gives you a much better starting place.

In What’s Next for My Career? I shared my journey of leaving my job as a lawyer and moving to a business development role at a startup. I was dissatisfied with my career, but I was having trouble identifying why. It took a few conversations with my first mentor, my mother, to identify what, exactly, needed to change and why. Those conversations led me to a long career in both legal and business roles at startups.

If you’re dissatisfied in your job, gather information before deciding how much needs to change. You may need a new role, clearer expectations, better boundaries, or an opportunity to use a skill that’s been languishing. You may also discover that a larger transition makes the most sense for you at this stage in your career. A mentor can help you test your thinking so you’re making a decision based on what you’ve learned, rather than reacting to one particularly miserable week.

Where are you headed now?

My career has taken me from practicing law and working with startups and technology companies to coaching and consulting. Each transition required me to ask what I wanted next and how my experience could help me get there. And mentors were a valuable part of this process.

At midcareer, it’s worth asking yourself the same questions. What work do you want to do? What energizes you? Who do you want to work with? What space do you want for your life outside of work? What you want may have changed, and your next steps should reflect that.

Start with one career question that’s been weighing you down and one person who could help you explore it. Make a specific request, prepare for the conversation, and follow through. You can be an experienced professional, mentor other people, and still benefit from someone else’s perspective.

Download the Workbook
I’ve created a practical workbook to help you start mapping your own mentoring and leadership support system. You’ll find prompts to clarify the support you need, identify your sources of power and influence, map key relationships, and prepare for more useful mentoring conversations. Download the Power, Perspective & Leadership workbook here and use it to choose your next step.

Want to Bring This Conversation to Your Group?
These questions come up in law firms, companies, nonprofits, bar associations, and leadership groups. How do you become more visible and influential? Build relationships that support your goals? Decide what comes next? I offer this topic as an interactive keynote, workshop, or mentoring program kickoff, tailored to your audience and the challenges they’re navigating.

If you’d like to bring Mentors and Why They Matter or Power, Perspective & Leadership to your firm, company, or group, reach out and let’s talk about what would be most useful. We’ll build a session that gives participants practical guidance and steps they can take in their own careers.