Three Envelopes
- cldaubney5
- Oct 6, 2023
- 3 min read
An executive assumes his new position and settles into his new office. As he explores the desk drawers, he finds them mostly empty, containing only a stray paper clip and a handful of lonely staples, missing a stapler. Typical of executive roles, there is no formal transition from his predecessor. After all, the higher you climb, the less time you have to enjoy the view on your way down, perhaps as storm clouds gather on the horizon.
To his surprise, he discovers three envelopes at the bottom of one drawer, each labelled with a number: one, two, and three. The first envelope has an inscription on it which says,
"To my successor. I want to impart my words of wisdom to you, which you can choose to heed or disregard as you see fit. In times of adversity, open these envelopes in numerical order, and I will guide you to avoid the same mistakes I made. I wish you the utmost success in your new role."

Recognising the value of such wisdom, he decides to keep the envelopes. Over time, they become buried beneath a clutter of Post-it notes, pens, and reports, fading from his memory.
As months pass, he reaches a pivotal point in his career where he feels vulnerable and doubts his ability to outperform his predecessor. Recollecting the three envelopes, he hurriedly sifts through his desk to locate them. Brushing away stale crumbs, he opens the first envelope to find just three words.
"Blame your Predecessor."
Intrigued, he promptly gathers his team to compile an issue and risk log, acknowledging the need to assess the present situation and understand why performance is not at its optimum. He takes responsibility for the situation, essentially blaming his predecessor for what he inherited. Surprisingly, this approach proves effective. His peers appreciate his honesty, and he experiences a profound sense of relief.
Life goes on smoothly for nearly a year. However, rumours circulate about his competence, with whispers of being "over-promoted" and inquiries about "what has changed." This time, he doesn't hesitate and opens the second envelope.
"Implement Restructuring."
He admires the brilliance of his predecessor, realising that this individual was misunderstood by the organisation but to his advantage. He initiated a comprehensive restructuring effort, reshuffling departments and implementing efficiency savings, much like a cabinet reshuffle.
The plan spans 18 months, but things take an unexpected turn after nine months. Anxiety grips him, akin to a contestant on 'Who Wants to be a Millionaire' facing a daunting question. Uncertain whether to utilise his final envelope or wait, the pressure at work fuels his paranoia. Finally, he reaches for the last, now coffee-stained envelope, hoping for guidance. It reads:
"Prepare Three New Envelopes."
If you find yourself identifying with this message, proceed with caution. And if you don't see yourself in it, chances are you know someone who embodies these principles. This doesn't mean you won't inherit your predecessor's differing viewpoints or that restructuring might not be the right course of action. However, these should not be the sole aspects that define your legacy. I heard this tale many years ago, and while I can't recall every detail verbatim, I've crafted my interpretation of its moral and live by it.
Embrace the courage to question the established norms; don't shy away from making mistakes, but ensure you extract valuable lessons from them.
Define what success means to you. What are your objectives for the initial 100 days? Define your path, whether it's projects, investments, personnel, systems, or strategies. Have you evaluated what you want to initiate, retain, enhance, or discard?
Be authentic. Remember that you were hired for who you are, not to emulate the individual who left behind three envelopes!





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