The Best Decisions Aren’t Made Alone
Who’s Missing from Your Biggest Decisions?Inside this issue
On My MindOne of the quiet pressures many dads carry is the belief that we’re supposed to have the answers. Whether it’s a career decision, a financial decision, or a parenting decision, we often assume the right answer is hiding somewhere inside our own heads. If we just think harder, research longer, or weigh enough pros and cons, we’ll eventually figure it out. The older I get, the less convinced I am that’s how the best decisions are made. This week on Gap to Gig, I sat down with employment lawyer and executive coach Natalie Holder. We covered career transitions, networking, workplace culture, and leadership. While we talked about careers and life and more, this conversations was all about how we make decisions, and why so many of us try to make them alone. Natalie encourages people to build what she calls a personal board of directors. It’s a small group of trusted people who bring different experiences, different expertise, and different ways of thinking to the decisions that matter most. Their value isn’t that they have all the answers. It’s that they help you see questions, opportunities, and risks you might never consider on your own. Every important decision has blind spots. No matter how thoughtful we are, we’re still limited by our own experiences. We naturally notice the information that supports our thinking and overlook the information that doesn’t. That’s not a character flaw. It’s simply part of being human. When I think back on some of the biggest decisions I’ve made, I don’t remember a moment where I suddenly figured everything out by myself. I remember conversations. Someone challenged an assumption I’d been carrying. Someone asked a question that completely reframed the situation. Someone shared an experience that helped me see a path I hadn’t considered. Those people didn’t make the decision for me. They helped me become a better decision-maker. Maybe that’s one of the most valuable roles relationships play in our lives. They don’t just encourage us when things get hard. They help us think more clearly before we act. The best decisions usually aren’t made alone. Don’t Make Big Decisions AloneWhy it MattersEvery major decision is shaped by the experiences you bring into it. The challenge is that your experiences are only part of the picture. Natalie recommends intentionally building a personal board of directors: a small group of trusted people who can help you think through important decisions before you make them. Their job isn’t to make the decision for you. It’s to ask better questions, challenge your assumptions, and help you see what you might otherwise miss. Where to BeginStart with the decisions, not the people Think about the kinds of decisions you regularly face. Maybe you’re considering a career change, trying to become a stronger leader, navigating the financial pressures of raising a family, or simply trying to be more intentional with your time. Once you’re clear on the kinds of decisions you’re making, ask yourself who already has experience in those areas. Look for different ways of thinking Your board doesn’t have to look like anyone else’s. One person might be a mentor who’s navigated challenges similar to yours. Another could be a subject-matter expert, someone in your industry, a fellow parent, or simply a trusted friend who’s willing to challenge your thinking instead of agreeing with everything you say. The goal isn’t to collect impressive titles. It’s to surround yourself with people who help you make better decisions. Invest in the relationship before you need the advice One of Natalie’s strongest points was that if you wait until you’re facing a difficult decision to build these relationships, you’ve waited too long. Stay in touch. Celebrate their wins. Share something that made you think of them. Offer help when you can. Then, when you eventually ask for their perspective, you’re continuing a relationship instead of starting one from scratch. Why it WorksThe goal isn’t to outsource your decisions. It’s to improve your judgment. Hearing different viewpoints doesn’t remove your responsibility to decide. It simply gives you a broader foundation from which to make that decision. The final call is still yours, but it’s informed by more than your own experiences. Pro TipThink about someone whose judgment you’ve respected for years, but haven’t spoken with recently. Reach out with no agenda other than reconnecting. Strong personal boards are built through genuine relationships, not transactional conversations. Change the QuestionWhy it Matters When we’re facing an important decision, our first instinct is usually to ask questions centered on ourselves.
Those questions aren’t wrong, but they only capture one side of the conversation. Natalie shared a story about negotiating two additional years of remote work with Stanford. What changed the outcome wasn’t a stronger argument. It was a better question. Instead of focusing only on why remaining in Maryland mattered to her family, she began thinking about why Stanford might benefit from that arrangement as well. That shift completely changed the discussion. Try This Before your next important conversation, rewrite the question you’re asking. A different question won’t always change the outcome, but it’ll almost always improve the conversation. Why it Works When you stop viewing a problem through only your own needs, you’re more likely to find solutions that serve everyone involved. That’s often where the best decisions begin. Pro Tip Before any important conversation, write down three reasons the other person might say “no.” If you can clearly explain their concerns before the conversation begins, you’ll almost always have a more productive discussion. Time to Sprint: Get Clear Before You DecideWhy it Matters It’s surprisingly easy to spend weeks trying to solve the wrong problem. We tell ourselves we need a new job when what we really need is a better manager. We think we need to earn more money when what we’re actually craving is more flexibility. Sometimes the solution is exactly what we think it is. Often, it isn’t. Before you make your next move, spend twenty minutes making sure you’ve correctly identified the problem you’re trying to solve. How to Do It Minutes 0–10: Name the real problem Most of us jump straight to solving the problem without first making sure we’ve identified the right one. That’s why it’s worth slowing down here. Write down one decision that’s been occupying your thoughts, then complete this sentence: “The real problem I’m trying to solve is…” Don’t stop at your first answer. “I need a new job” might actually become “I don’t have enough flexibility,” “I no longer believe in the work I’m doing,” or “I don’t see a future here.” Each of these leads to a very different solution. Minutes 10–15: Define what success actually looks like Once you’ve identified the problem, get specific about the outcome you’re after. Natalie asked a revealing question during our conversation: “What does more meaningful actually mean to you?” Take a few minutes to write a short paragraph describing what success would look like a year from now. Instead of using words like better or more meaningful, describe what would actually be different. What would your days look like? What would you have more time for? What would you stop worrying about? The clearer the destination, the easier it becomes to evaluate your options. Minutes 15–20: Invite another perspective Now think about who could help you see this situation differently. Write down one person’s name and one question you’d genuinely like to ask them. Instead of asking, “What should I do?” try asking, “What’s something you think I might not be seeing?” You’re not looking for someone to make the decision for you. You’re looking for someone who can help you make a better one. Why it Works Most of us spend more time evaluating solutions than defining the problem. This exercise flips that process. By identifying the real issue, defining what success looks like, and inviting another perspective before you act, you’re much more likely to make a decision you’ll still feel good about months from now. Pro Tip If the solution you’re considering is the first one that came to mind, challenge yourself to write down two more. The best option is rarely the first one you think of. Your MoveWho’s someone that helped you make one of the best decisions of your life, and what did they help you see? Hit reply and let me know. I read every response. Connect with NatalieNatalie Holder is an employment lawyer, executive coach, speaker, and founder of Quest Employment Initiatives. Throughout her career, she’s helped professionals navigate career transitions, workplace conflict, leadership challenges, and high-stakes employment decisions. What I appreciate most about Natalie’s approach is that she doesn’t separate career success from personal fulfillment. She encourages people to define what meaningful work actually looks like for them before chasing the next opportunity. Follow Natalie On her websites: https://www.questei.org and https://www.natalieholderspeaks.com On YouTube: https://www.youtube.com/@QUESTEmploymentInitiativesLLC On LinkedIn: https://www.linkedin.com/in/natalievholder/ On the Show This WeekContinue the ConversationThe best career advice isn’t always about your career. Natalie shares practical strategies for making better decisions, building stronger professional relationships, and defining success on your own terms. Along the way, we explore why the people you surround yourself with often shape your future more than any single opportunity. In this episode, we discuss:
Check it Out🎧 Natalie Holder on Why Working Dads Need a Personal Board of Directors Listen on your favorite podcast platform The Last LaughNo words needed…
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