Why Am I Still Working?

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I recently read an article by Robin Robins titled Why Are You STILL Working?! It made me smile because I’ve been asking myself that exact question a lot lately.

Robin and I have never met, although I’ve watched her career from afar for years. She is certainly not afraid to have an opinion, and whether you agree with her or not, you have to admire her moxie. Her article got me thinking about my own reasons for continuing to work when, by most definitions, I don’t need to anymore.

I’ve been fortunate in my career. I founded and sold three companies, and for the past several years I’ve had the privilege of helping other technology business owners do the same. Financially, I’ve reached the point where continuing to work is a choice rather than a necessity.

So why am I still doing it?

For a while, I thought the answer might simply be that I hadn’t figured out how to stop.

I’ve been working since I was young. I became a CPA, started companies, built them, sold them, and eventually created an entirely new career advising technology business owners through M&A. Along the way, I wrote Get Acquired for Millions, a book about preparing and positioning a technology company for a successful sale. There has always been another company to build, another problem to solve, another goal to reach.

Of all the different aspects of M&A, my passion has always been the sell-side. Maybe that comes from having sat in the seller’s chair three times myself. I understand how personal the decision to sell can be and how much is riding on getting it right. For many owners, the value locked inside their business represents decades of work and a significant portion of their net worth. Helping them maximize that value and successfully navigate a transaction is the part of this business I still find incredibly rewarding.

When you’ve spent most of your adult life doing that, retirement sounds wonderful in theory. Travel more. Spend more time at our homes in Oregon and Kauai. Ski. Swim. Knit. Read. Have absolutely no idea what day of the week it is.

There are days when that sounds pretty darn good.

But I’ve also started to realize something about myself.

I still like the game.

I like sitting across from a business owner and telling them what I think their company is worth. I like figuring out which buyers will recognize that value and which ones won’t. I like getting five LOIs and seeing five completely different ways buyers have structured essentially the same transaction.

And, perhaps more than anything, I still like the moment when a deal gets complicated.

A buyer retrades the purchase price. The Quality of Earnings uncovers something unexpected. Working capital becomes contentious. Two offers look similar on the surface but are dramatically different once you understand the terms. A seller calls because they don’t know whether to push back, compromise, or walk away.

After nearly 40 transactions, I’ve seen a lot of those situations. And I still get tremendous satisfaction from being the person who can say, “I’ve seen this before. Here’s what I think we should do.”

But there is another side to this.

I don’t love every part of the work anymore.

Some of the things that used to interest me simply don’t. I don’t need to be copied on every email. I don’t need to manage every item in a data room. I don’t need to personally drive every step of a four-to-six-month transaction.

For a while, I confused being tired of those things with being tired of M&A. They aren’t the same.

One of the biggest reasons I’ve been able to make that distinction is Katie Spokely. Over the last several years, Katie has steadily taken on more responsibility at RoseBiz. Today, she is often the primary point of contact for our sellers, managing the details of a transaction and keeping the process moving while I step in where my experience can have the greatest impact.

And she is exceptionally good at it.

So, I’m also using this article to make an announcement that is probably overdue. Katie has been promoted to Director of M&A Advisory Services at RoseBiz. The title really just catches up with the job she is already doing.

Katie enjoys many of the details that, after all these transactions, don’t particularly excite me anymore. She has also given me the ability to spend more of my time on valuation, buyer strategy, negotiations, and the inevitable curveballs that arise between signing an LOI and closing a transaction.

And something unexpected happened.

I started enjoying the work more again.

That has changed the way I think about retirement.

Maybe retirement doesn’t have to mean waking up one morning and declaring that I’m finished. Maybe after spending decades building experience, the goal isn’t to stop using it. Maybe the goal is to become much more selective about how I use it.

I can work with fewer companies. I can choose the transactions that interest me. Katie can run much of the process while I focus on the places where experience and pattern recognition really matter.

And I can say no.

That may be the greatest luxury financial independence has given me.

For most of our careers, we work because we have obligations. Mortgages. Kids. Retirement accounts. Employees. Businesses that depend on us. Even when we enjoy what we do, there is an underlying requirement to keep producing.

Eventually, if we’re fortunate, that changes.

You no longer have to work.

And that’s when you get to ask a much better question:

What work would I choose to do if I didn’t need the money?

I’m beginning to understand my answer.

I want to keep doing work where my experience matters. I want to work with people I like. I want interesting problems. I want the occasional difficult negotiation that gets my adrenaline going. I just don’t want it to consume my life.

So yes, I’m still working.

Not because I have to. And not because I can’t imagine a life without work. I’m still working because there are parts of what I do that I genuinely love, and I’ve finally earned the ability to keep those parts and let go of many of the others.

Maybe that’s not retirement.

But right now, it feels like a pretty good definition of success. Besides, I’m not entirely sure my husband wants me completely retired either. I have a feeling his honey-do list would grow exponentially.