The End, the Messy Middle, and the New Beginning—How to Get It Right


The End, the Messy Middle, and the New Beginning—How to Get It Right

Life has a way of throwing us into transitions whether we’re ready or not. Jobs end, businesses close, relationships shift, and entire chapters of our lives wrap up—sometimes with closure, sometimes with a lingering “what now?” If you’ve ever found yourself in that uncertain space between what was and what’s next, you’re not alone.

The End: When the Ground Shifts Beneath You

Endings can be brutal. Whether it’s a business venture that didn’t work out, a career shift, or a major life change, the first reaction is often shock. I know this feeling well. When I had to close the chapter on a company I’d poured years into, I felt like I had failed—not just as a business owner but as a person.

The pain wasn’t just financial; it was deeply personal. The sense of identity I had tied to my work was suddenly gone. I’d spent years being the CEO, the leader, the problem solver. And then, overnight, I wasn’t.

The hardest part about endings? They feel permanent. But they aren’t.

The Messy Middle: When Everything Feels Uncertain

This is where the real work happens. The in-between space is uncomfortable, unpredictable, and full of doubt. You don’t yet have a clear vision for the future, but you also can’t go back to what was. It’s a foggy, frustrating, necessary part of the journey.

When I found myself in this space, I had more questions than answers. Should I start something new? Get a job? Take time off? I was used to action, used to having a plan. And yet, the messy middle demanded something different: patience.

This is where many people give up or settle for something that doesn’t feel right—just to escape the discomfort. But the messy middle is where we grow. It’s where we reflect, reassess, and redefine success.

The Start of Something New: Building the Next Chapter

Then, one day, clarity starts to creep in. Maybe it’s a new business idea. Maybe it’s a realization that a different path is calling you. Maybe it’s simply the decision to stop waiting and start building.

For me, the next step was stepping back into entrepreneurship, but with a fresh perspective. Instead of clinging to my past successes (or failures), I asked: What do I actually want? What kind of impact do I want to have?

Starting something new doesn’t mean you erase what came before—it means you integrate the lessons. And when you do, you move forward stronger, more focused, and more intentional.

Your Next Transition

If you’re in the middle of a transition right now, I won’t sugarcoat it—it’s tough. But it’s also temporary. Every ending leads to a beginning. Every messy middle is a chance to grow. And every new start is an opportunity to redefine your path.

So if you’re feeling stuck, remember: This isn’t the end of your story. It’s just the messy, necessary middle. And something new is on the way.

If this resonates, I’d love to hear about your own transitions. What chapter are you closing? What are you stepping into next? Let’s navigate this together.


For federal employees facing unexpected layoffs, this transition can feel especially overwhelming. The job security you counted on is suddenly gone, and it’s easy to feel lost. But getting the end right is critical to setting yourself up for what comes next.

Here’s what you need to do first:

  • Understand Your Benefits – Know what severance, retirement options, and unemployment benefits you’re entitled to.
  • Clarify Your Financial Picture – Take stock of your savings, expenses, and any emergency funds to make a game plan.
  • Leverage Your Network – Reach out to peers, mentors, and industry contacts to explore new opportunities.
  • Allow Yourself Time to Process – It’s okay to grieve the change, but don’t get stuck there.

To make this transition easier, I’ve put together a step-by-step guide to help you navigate the end effectively.

Download the toolkit here to get the fundamentals right and move forward with confidence

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I’m Craig Isakow, a former federal employee who transitioned into entrepreneurship. My wife, a career public servant, recently left the federal government, and I was there to support her every step of the way. Through that experience, I saw firsthand how overwhelming career transitions can be—navigating benefits, understanding finances, and figuring out what’s next.

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