Managing The Messy Middle In Your Projects (& Your Career)

Managing the Messy Middle In Your Projects (& Your Career) _ Red Cape Revolution

If you’re engaged in any work that’s worthwhile, I can promise you this:

It’s going to have a messy middle.

That big project you’re leading at work? I don’t care how many times you’ve run the same plan before, it’ll all fall apart somewhere before everything falls into place.

Your carefully navigated career? The days of the constant upward trajectory are over. Actively managing mid- and late-career challenges is more essential than ever.

Yup, the only thing without a messy middle is a donut.

the only thing without a messy middle is a donut

Why Messy Middles Happen

Messy middles–that point when everything seems to be falling apart–happen to everyone.

Sorry—you won’t be immune.

Often, the mess is triggered by a missed deadline, broken expectation, or a series of mistakes happening at once.

Or as Adobe chief product officer Scott Belsky says in his upcoming book  The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture (affliate link),  it’s the “bumps in-between” the path from nothing to something.

Alternatively, the messy middle can be triggered by a date, such as the start of a new week, month, year, or even the first day back to work after a national holiday or break.

Author Dan Pink describes this phenomenon in his book, When: The Scientific Secrets of Perfect Timing (affiliate link).

Pink cites University of Pennsylvania research that discovered that these calendar triggers become “temporal landmarks,” which, like physical landmarks, stand out in our brains, make us slow down and take notice, and think more consciously about what we’re doing next.

landmarks make us slow down and notice

But whether your messy middle is sparked by a problem or by the calendar, try these three strategies to help manage the mess without messing up your life.

How to Manage the Messy Middle: 3 Strategies

Strategy 1: Teach Others to Expect the Mess

My client Barb was an experienced consultant, and as so, a black belt expert in the management of the messy middle, with certification from the school of hard knocks.

So, as she’d done many times before, she stood in front of the room of clients and stakeholders as she outlined the project that was about to begin.

“Here’s what always happens,” she described.

“We start with a ton of spirit and energy–like you all have today.

“In a little while though, the work will start to feel harder. Things that we’ve planned out now will have to be revisited or changed. That’s okay–it’s a natural part of collaboration.”

Heads nodded.

“At some point, though, everything will feel like it’s falling apart. Someone in this room–or maybe several of you–will start to freak out.”

The SVP of HR suddenly peered at her over his Warby Parkers.

Undeterred, Barb waged on.

“But you need to know now that the messy middle is normal–especially for a project as complex as this.”

“It always happens.”

Barb–and other smart internal and external project leaders I’ve worked with–all find the same thing: when you take time in advance to let others know you’re expecting the messy middle, it’s less surprising and upsetting when it actually happens.

It’s a sure-fire crystal ball moment.

it's like you have a crystal ball at work

If it doesn’t happen, no one will remember you said it would. They’ll all be happy that all’s well.

But (and this is the most likely scenario) when the mess does happen, we can point back and say, “Hello, Mess–we’ve been expecting you.”

And like your annual visit from Aunt Martha, because you know she’s coming, you don’t scramble and flail when she knocks on your door.

Teaching others to expect the messy middle is not only a brilliant project management strategy, it’s also one of the kindest things you can do for your teammates and for yourself.

Let ’em know they’re normal. They’ll thank you.

Strategy 2. Prep Your Mess Management Plan

Since you already KNOW that at some point things will be a mess, what can you do NOW to be ready for THEN?

Start today by building your 3Rs:

  • Resources
    • Projects and transitions fail when people only plan for the minimum amount of time, money, talent, and even energy that will be needed. You can be different. Align the resources up front so that you’re not scrambling for more during the middle when you may naturally feel defensive, depleated or even just tired.
  • Relationships
    • Who are the people who you can count on to help you through the mess? Perhaps they’re inside your company, or perhaps they’re external professionals like a mentor or coach. Who do you need to bring up to speed now so that you won’t waste time when you need them later?
  • Resilience

When you’ve built the resources, relationships, and resilience, you’ll manage any messes with ease.

Strategy 3. Let Time Do Its Work

Sometimes it’s hard to see your way out of the mess.

You’re angry, frustrated, or annoyed. Maybe tired, discouraged, and ready to give up.

Wait.

There’s another tool you can use here.

And it’s absolutely free. Plus,  it runs itself, so you don’t have to.

It’s the calendar.

The passing of days. Sunrise, sunset.

let time manage the messy middle for you

Because no matter how much you do or how hard you work, time will continue to pass.

And it can be the perfect solution.

Sometimes, the best thing we can do when we’re in a mess is to let it sit.

Not forever, but maybe for now.

Get some rest. Create some distance.

The world is always churning and situations change.

People change. Their perspectives change.

If you can’t seem to find your way out of the mess, maybe you need to give it a day.

Walk away for now. Sleep on it.

The world keeps spinning; the clock keeps ticking.

Know you’re not the first to be in the messy middle. If you use these strategies, you’ll find your way out.


If you’re feeling stuck in the messy middle of your career, perhaps you need to finally decide whether to stay or leave your job. Check out my on-demand video course, “Should You Stay or Go? Make Your Best Career Decision,” and start moving past the middle toward what’s next for you.


Read this next:

What to Say to Yourself in the Middle of the Night: Career Strategies