Is the buy-side still right for this next chapter of my life?

Candidate: "I think I need to leave the buy-side."

Me: "Tell me more..."

Candidate: "I'm having my first baby soon. This lifestyle is not compatible."

Me: "Do you still enjoy investing and working with management teams?"

Candidate: "Absolutely."

Me: "Do you still get excited about deals?"

Candidate: "Of course. I'm just struggling with the environment and culture."

Me: "If you could do the same job with leaders whose values and firm culture aligned with yours, would you still want to leave?"

Candidate: "No."

I've been having conversations like these at least once a month for as long as I've been recruiting for the buy-side.

Too often, talented investors assume they need to abandon a career they've spent years building when what they really need to question is whether they're in the right environment.

Because leaving a firm and leaving an industry are two very different decisions.

In my experience, I find that many professionals are trying to answer the wrong question.

The question shouldn't be: "Should I leave the buy-side?"

The question should be "Is this the right firm for the next chapter of my life?"

In the case of my candidate, she wasn't questioning investing. She still loved deals and working with management teams. She still loved the intellectual challenge of evaluating businesses.

What she was questioning was whether the environment around that work aligned with the person she was becoming.

The baby didn't create the issue. It simply accelerated a question she may have eventually asked anyway: "Is this the right firm for the next chapter of my life?"

So what advice did I give her? Well, I didn't give her career advice.

Instead, I told her to think like an investor. Annoying, I know.

Investors know better than anyone that you shouldn't make major decisions without sufficient data. And that's exactly what I thought she was missing.

She wasn't ready to decide whether she should leave the buy-side. She first needed to determine whether she was solving the right problem.

So I gave her homework.

1. Define Your Non-Negotiables 

Most people start looking for a new opportunity before they've clearly defined what they need. That's backwards. Before speaking with another recruiter, another firm, or another hiring manager, get clear on what matters most. Ask yourself:

• What does support actually mean to me?

• What leadership behaviors build trust?

• What am I no longer willing to tolerate?

• What would make me excited to stay somewhere for the next five years?

You can't identify the right opportunity if you haven't defined what "right" looks like. 

But in my candidate's case, this was her first baby and she was still 6 weeks out. How is she supposed to know what she's going to need in 6+ months time?

Well, she won't...and that's ok. The point is to get as clear on what's important to you at this stage. Will your priorities change once you're in the thick of things. Of course. They will evolve so keep doing your diligence. Which leads to point two.

2. Find Women Who Are Living the Life You Want

One of the biggest mistakes I see women make is making assumptions about what's possible without talking to women who are already doing it.

If you're wondering whether motherhood and a senior investing career can coexist, don't ask LinkedIn or ChatGPT. Find women who are actually living it. Ask them:

• What changed after becoming a parent?

• What support mattered most?

• What surprised you?

• What would you never compromise on again?

• What did your firm get right?

• What did your firm get wrong?

• If you were evaluating firms today, what questions would you ask?

You're not looking for advice so much as patterns. The more patterns you uncover, the more informed your decision becomes.

3. Stop Evaluating Jobs And Start Evaluating Ecosystems

Most candidates spend all of their energy trying to prove they're the right fit. But the best candidates spend just as much time determining whether the firm is the right fit for them.

I encouraged her to stop evaluating jobs and start evaluating environments.

Questions I would ask:

• How many women are in leadership?

• How many of them have children?

• Can you tell me about women who became mothers while working here?

• Were they promoted after becoming parents?

• Can leadership point to examples of women successfully navigating this stage of life?

• How do leaders talk about family when nobody is recruiting me?

• How does the firm support flexibility in practice, not just in policy?

Watch what happens next. Strong cultures usually have immediate examples. They'll tell stories and point to people. They'll proudly discuss career progression.

Weak cultures tend to answer with policies, but strong cultures will answer with names.

And don't get me wrong. Policies matter, but examples matter more. After all, almost all firms will say they support working parents, but not every firm can prove it.

Find Your Tribe, Not Your Exit

The buy-side is not exactly known as a beacon of work-life balance. I get it. But I've also spent years watching women build incredible careers in private equity, credit, and venture capital.

I've seen many become partners, raise families, found their own firms. I've also seen women leave environments that weren't serving them, only to thrive elsewhere.

Not every firm is going to be the right fit. Not every culture is going to be the right fit. Not every leadership team is going to be the right fit. And that's okay. The goal isn't to find a perfect job. The goal is to find a place where your professional ambitions, values, and life stage can coexist.

Sometimes the answer IS leaving. But before you leave the buy-side, make sure you've diagnosed the right problem. Because sometimes the answer isn't finding an exit.

Sometimes it's finding your people. Your leaders. Your tribe.

I've spent years helping buy-side professionals navigate career transitions, and one thing I've learned is this: the best decisions are rarely made in isolation. Talk to people who are living the life you want, ask better questions, and don't be afraid to challenge your own assumptions. Your next chapter deserves that level of diligence.