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CIO Career Advice From The Future

How to start a revolution at work by flattening the org, taking part in hackathons, and listening to rap music.

There's no hope for change after 30.

That's my completely scientific conclusion after compiling the chart below, which shows the number of Google search results for "letter to my (n)-year-old self."

Nobel Prize, here I come.

The takeaway: Any letter that you write to your 30-year-old self should refrain from sage advice and simply list winning lottery numbers.

That said,

Dear 30-year-old self (circa 1998):

Middle management is a ring of hell
You're stuck there right now. And oddly, you're enjoying it. Don't get comfortable. Your long-term goal shouldn't be to retire to senior management but to flatten the org.

That's a tough goal if all you have is middle management's "soft power." No autonomy. No ability to make the executive decisions. Poor wittle you. You still haven't figured out that middle management is a tiny evolutionary hop from the roles played by our fathers' secretaries. If senior management had the stomachs for it, they'd call you executive assistants. Not an assistant manager, but an assistant to the manager.

Thank God you still think you're 20. You have a healthy disrespect for authority. You understand that operating with autonomy is a choice, your choice, and not a gift from your boss. And that understanding is the secret key to the executive washroom. It'll be yours soon.

Be careful, though, because the higher you get in an organizational hierarchy, the more ambivalent you get toward the benefits of position in that hierarchy. That's why executives have better health and eye plans. They suffer from shortsighted, self-serving myopia.

Sadly, your peers in middle management don't understand any of this. Or if they do, they keep passing the alcoholic the drink.

The good news is that even talking about flattening the org will force them to question their own value. Why have a layer between senior management and the frontline? Couldn't they turn top-line strategy into action? Couldn't they manage the day-to-day?

Despite what senior management wants everyone to believe, setting top-line strategy isn't a full-time job.

Hell, it's not even a part-time job. You know what is a full-time job? Challenging the current power structure. Do it. Not because that'll get you into an executive role (it definitely will), but because it's principled dissent.

Disrupt your whole layer out of their comfort zones and eventually out of their jobs. That last part sounds mean, but don't worry about what all those middle managers will do next. All the people you've known who have left the company have landed on their feet. And quickly. Most of them wonder what you're still doing there.

You should wonder that, too.

Corporate lifers -- especially in IT -- make all kinds of false assumptions about their own employability. From the outside they look like people trapped in an abusive relationship. "Oh, he loves me. He has a good heart. He's better than this."

But it's not about him. It's about you and how you fail to see that you deserve better. You stay at your current employer partly because it's convenient, but mostly because you don't understand how much you're worth. The trick is to realize how much but stay humble. And no, you still haven't figured out that piece of the puzzle. It'll probably be a deathbed revelation.

Speaking of which,

Senior management is asleep
Don't wake them. They look so peaceful.

Read the full article on InformationWeek.

About The Author: The author, a senior IT executive at one of the nation's largest banks, shares his experiences under the pseudonym Coverlet Meshing. He has spent the last two decades in the financial services sector, picking a fight with anyone who doesn't understand that banks are actually software companies and need to invest in engineering as a core competency. His cheery outlook and diplomatic nature are rarely reflected in his writing. Write to him at

The author, a senior IT executive at one of the nation's largest banks, shares his experiences under the pseudonym Coverlet Meshing. He has spent the last two decades in the financial services sector, picking a fight with anyone who doesn't understand that banks are actually ... View Full Bio
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