Business Breakups: Forging Your Path

This article was originally published on Citywire, authored by Melissa.

In our personal lives, we know what to look for when a relationship starts to go sideways. At least I have an idea of what that may resemble in my own life - the good, the bad, and the ugly. 

You stop feeling heard. 

Trust erodes. 

The future feels fuzzy instead of full of possibility. 

And at some point, if we’re lucky and self-aware enough, we decide to walk away in pursuit of alignment, peace, or just plain freedom. Easy peasy… said no human ever.

But in business? We often don’t give ourselves that same permission. In fact, we rationalize misalignment better than the best. We tell ourselves it’s just a rough patch. We let “professionalism” or loyalty keep us tied to relationships, processes, and partnerships that are no longer working for us, with us, or by us. 

And let me tell you, candidly and transparently, I’ve been there. More than once.

Over the course of my career as a financial planner and business owner, I’ve had three major business breakups; one with a business partner; one with a substantial vendor, and one with an entire back-office team. Each one took too long. Each one drained more energy than I care to admit. And in every case, the signs were there long before I made the move. Like any relationship that needs to end, hindsight is a bear. 

This article is for anyone who feels stuck in a business relationship that just isn’t working, especially those of us in the financial advising world, where loyalty is prized and “making it work” is often valued more than knowing when to walk for your own good.

Let’s talk about why we stay, how we know when it’s time to go, and what can happen on the other side of a business breakup.

The Slow Fade: The Life Cycle of a Business Breakup

Rarely do business relationships blow up in a single dramatic, fiery moment. It’s not usually a slammed door or a shouting match, although even the most level heads don’t always prevail. Instead, it’s often a slow, uncomfortable but mostly silent fade.

It looks like this:

• You find yourself avoiding meetings or dreading conversations.

• You start doing workarounds to avoid a system or process that isn’t serving you.

• You mentally check out when your business partner speaks, or emails, or messages you, or worse, you stop trusting what they’re saying altogether.

• You justify rising costs or poor performance because things used to be different.

In my own experiences, each breakup began quietly. My partner and I had great synergy in the early days, so much so that it was palpable. As our values evolved, because we’re human, our communication faltered and that slow burn of destruction began. That sounds dramatic, and it should. The result of this fading out is deadly to business.

We stopped being collaborative and started being transactional. Our communication was on a need-to-know basis, making it impossible to be in actual partnership. With the vendor, what began as a great tech fit for the firm turned into an overpriced, underperforming mess that not only confused us but our clients. And with the back-office team? It became clear that their priorities no longer aligned with how I wanted to serve my clients or operate as a firm in the industry.

But because things didn’t fall apart instantly, I kept telling myself they weren’t really broken. 

With all three.

That’s the trap: the slow fade keeps us invested just enough to stay stuck.

Red Flags We Talk Ourselves Out Of

Let’s be honest, shall we? Most of us see the signs; we just don’t want to believe them.

Here are a few red flags that, in hindsight, were crystal clear on my journey as a firm owner. Tell me if these ring a bell or hit you hard in the gut:

• The trust is gone. Whether it’s about money, performance, or integrity, once trust is broken, it’s incredibly hard to rebuild. It is even harder to operate without.

• You’re doing their job. If you're constantly cleaning up after a partner, reworking a vendor’s deliverables, or carrying the weight of a one-sided relationship, that’s not collaboration. That’s dysfunction, and it’s expensive.

• Your values are no longer aligned. When you're compromising your core beliefs just to keep the peace - or worse, just to get things done - that’s a problem.

• You’re not growing. This might be the most important sign and one that personally takes me out. If the relationship is holding you back from stepping into your next level of business, it’s already costing more than it should. Time to go.

In each of my breakups, these signals were flashing like huge neon signs above the office door, every morning I walked in. And I still hesitated. Why? Because breaking up is hard. Even in business. 

Business owners can say that removing the emotion from business partnership in any capacity is the solution to this. Let me reiterate that we, all, are humans (as far as I can tell), and that is not a fair or realistic ask of anyone. So, again, breaking up is hard. Even in business. 

Why We Stay (Even When It’s Time to Go)

There’s a strange sense of loyalty that shows up in business, for some. I know for me, especially in this world of financial advising, the long-term is always the focus. We guide clients to think this way, and in business, we’re taught to do the same. Invest in your firm, your people, your tech, your support, and give it time to bake in the oven before deciding if it's worth keeping or tossing. We’re trained to think long-term. To honor relationships. To stick it out.

And that’s not a bad thing. But it can and often does become a barrier to growth.

Here are the reasons I stayed longer than I should have:

• Fear of disruption: I didn’t want to lose momentum, scare clients, or risk a messy transition.

• Guilt: I worried I’d look like the bad guy for walking away from a partner that used to work and that used to be part of my identity.

• Hope: Maybe it would turn around. Maybe we could fix it. (Spoiler: we couldn’t.)

• Pride: I didn’t want to admit that a relationship I had poured into — for years — just wasn’t working anymore.

All of these reasons are valid. But none of them should keep you in a relationship that’s stifling your growth or harming your business. Here’s why.

What It Cost Me (Before I Walked Away)

The true cost of staying isn’t always measured in dollars. However, please trust me when I say, the financial cost was very real. But even more than that, the losses were notable: 

• Time lost in ineffective meetings

• Emotional energy spent managing tension

• Opportunities missed because I couldn’t fully show up

• Clients not getting my best work, because I was spread too thin or constantly distracted

I was physically sick for a portion of my past bad business relationships. I couldn’t manage the relationships or figure out how to safely exit, and the stress that came with landed me in the hospital more than once. It’s easy to look back now and say, I should have left sooner. But at the time, it felt easier to stay than to face the unknown.

Until one day, staying wasn’t easier anymore. It was unsustainable.

The Breakup Blueprint: How to Leave with Your Mental Health Intact

Leaving a business relationship doesn’t have to be dramatic or destructive. Scorched-earth is a term I like to throw in the mix when talking about this subject, but it is not a requirement. In fact, some of my best transitions happened with clear communication and respect, after I got honest about what I needed.

Here’s what I’ve learned about how to make a business breakup healthy and productive when possible.

1. Get Clear on Your Values. Before you take any action, revisit your why. What do you stand for? What kind of business do you want to run? If the relationship doesn’t support that vision, it’s okay to let it go.

2. Communicate Directly and Compassionately. Name the issues. Don’t sugarcoat, but don’t burn bridges either. Be clear about what’s not working, and why. Often, the other party already knows, but you might be surprised at what they don’t.

3. Build a Transition Plan. Whether it’s finding a new provider, shifting client communications, or reworking internal workflows, give yourself time and space to plan a clean exit. Everyone on the team is impacted with these types of moves, so be sure to evaluate the full scope of that impact first.

4. Reflect and Document the Lessons. Every breakup taught me something. About my blind spots, my boundaries, my leadership, and what I need to work on for my own personal and professional growth. Take time to write down what you’ve learned so you don’t repeat the pattern.

   
   

What’s Waiting on the Other Side

Every time I walked away from a misaligned relationship, something better emerged.

More clarity. More energy. More space to create, lead, and grow. And, of course, a clearer understanding of what mattered most to me moving forward.

The right partnerships enhance your work. They bring ease, not tension. Trust, not second-guessing. When you find those, you’ll wonder why you ever settled.

Business breakups aren’t about failure. They’re about evolution. Sometimes we outgrow a process, a provider, or even a person. That’s not disloyalty, for the curious. That, friends, is leadership and growth.

To anyone reading this who feels stuck: you already know what’s not working. You don’t need more proof. You just need permission. Let this be it. Breakups are hard but staying stuck is way harder, and likely more expensive, emotionally, physically, and financially. Trust that you know what’s best for you and your business and make the moves necessary to support that, today.