Stop Climbing the Wrong Ladder

A colleague landed what they thought was their dream job, a senior leader for a Fortune 100 company. The title alone had weight. They packed up, relocated near headquarters and walked in ready to operate at the highest level of corporate America. Then something subtle started happening. Every time we caught up, the spark was a little dimmer. The stories shifted from excitement about the work to exhaustion from the politics. The messy, territorial, surprisingly petty politics. Eighteen months later, they walked away from the ladder they had spent years climbing and they haven’t looked back. The ladder was real. The dream, it turned out, belonged to someone else.

Before You Climb, Check the 3Ts: Trade, Target, Toll

Most career advice tells you how to climb the ladder faster. Yet we rarely pause to ask if the view at the top is even worth the trek. Before you invest another year climbing another step, consider the hard truth: the wrong ladder does more than waste your time. It drains your health, strains your relationships and quietly trades your well‑being for someone else’s definition of success. Here are the questions worth sitting with before your next big move:

• Trade: What are you really giving up? Every job trades something. Time. Energy. Relationships. The right ladder trades things you have in abundance. The wrong ladder trades things you cannot get back. My colleague traded their joy for a corner office. That trade only makes sense if your values are aligned with your gains.
• Target: Are you aiming for the right target? Look closely at the people already in that role. They reveal the reality you’re aiming for. Do you admire their character or just their compensation? If you cannot tolerate their daily reality, you will not survive at that level. Culture is not theoretical. It is demonstrated daily by the people who succeed within it, which means you should pay attention to the patterns.
• Toll: What is the long‑term price of operating here? Not the workload you think you’ll have, but the one leaders actually carry. Before you commit, study how leaders in that environment actually spend their days. Are they constantly in crisis mode? Do they have space to think, strategize, and lead? A role that requires perpetual urgency or chronic overextension isn’t a leadership opportunity: It’s a burnout pipeline. Understanding the true demands of the job before you step into it protects you from climbing into a lifestyle that quietly erodes your well‑being.

The wrong ladder can look perfect until you are halfway up and realize it’s not what you imagined. Leaders make better choices when they pause long enough to question the climb, study the culture and choose paths that strengthen your leadership instead of draining it. Sometimes that means changing your corner office. Sometimes it means walking away from the ladder altogether. Either way, make sure the view at the top of your ladder is one you actually want to wake up to.

Adeline (Addy) Maissonet is a senior advisor on contracting policies and procedures within the Office of the Secretary of War, U.S. Department of War (DoW) and the agency’s representative on the Department’s views on proposed legislation to Congressional members, their staff, and committee staffers. She leads the development and implementation of Department-wide procurement policies for commodities and services, within her portfolio. Prior to her current role, Addy served as a Division Chief and Contracting Officer with unlimited warrant authority for the U.S. Army Mission and Installation Contracting Command (MICC) – Fort Eustis, Virginia. Prior to joining the MICC, Addy served as a Branch Head for the Mid-Atlantic Regional Maintenance Center (MARMC), Norfolk, Virginia, with unlimited warrant authority. She also held other procurement positions with the U.S. Navy. Addy holds an MBA in Management and Contracting Level III Certification under the Defense Acquisition Workforce Improvement Act. She is a graduate from Cornell University’s Executive Leadership Certificate Program and Harvard University’s Business Analytics Certificate Program. In her free time, Addy enjoys hiking and overlanding with her family and friends.

Note: The views and opinions expressed in this article are those of the author and do not necessarily reflect the official policy or position of the Department of War.

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