Breaking Glass

“A very convenient way to always be a victim in the rain.”

That was the quote that a director at McKinsey wrote to a female academic referencing her work on the glass cliff. The glass cliff is the idea that women are more likely to get the top job at companies once the company is in trouble.

This director lost his job quickly, but this is not a one-time mistake by one man. This is a symptom of a much larger problem.

That a smart man, and let’s be honest, a total idiot is not ascending to partner at McKinsey, feels comfortable putting something like that in writing is a sign that we have taken our foot off the gas pedal.

Just as we achieve some progress, we risk regressing because we lull ourselves into the belief that the problem is no longer a problem.

As a woman in the workforce, I can say with confidence: we have not solved the problem.

Women earn more than half of all college degrees, yet they make up roughly 10% of the top jobs at Fortune 500 companies. That is a problem. And it is not an accident.

Women are not behind because they are less capable or less ambitious. It is much more complicated.

Almost a decade ago, I found myself having a lively conversation with an older woman at a wedding. Her peak career years had been in the 80s and 90s, and she started talking about how hard it was to be a professional woman back in the day.

The conversation started with familiar details about always being asked to fetch the coffee, take meeting notes, or make copies, even after she was promoted to senior roles.

Then the conversation turned dark.

She shared how during a business trip, a male co-worker tried to assault her. She managed to escape before anything happened, locked herself in her hotel room, barricaded the door, and spent the rest of the night alert, terrified that he might come back and try to force his way in.

The next morning, the co-worker acted like nothing had happened. She reported his behavior to HR. Nothing came of it.

She concluded her story by saying that even though it had been awful, she was happy because it had paved the way for women today to have equality in the workforce.

I debated whether to nod in agreement, but I had to say it.

“Actually, we have not achieved equality just yet.”

I then shared my own story as a professional woman. My experience was nothing like hers. I have always felt physically safe at work, even in rooms full of men. But inequality has many forms.

I had been working at a company for a few years, waiting for a transfer. Year after year I was told to wait. Wait for the new budget to arrive. Wait for an open headcount. Wait until the new team is fully trained. Wait to complete the newest implementation.

I waited. And finally, years in, there was an actual opening at the department I wanted to transfer to. Someone had given his two-week notice. Within hours, the position was filled with an outside candidate.

I couldn’t even understand how this could happen. This was a company that took months to hire for even the most junior of roles.

The person who received my role was the accounting intern from the previous summer. While I had years of experience inside and outside this company, this kid was signing up for his first job out of college. I also had a master’s degree and a couple of certifications on him.

I was not going to take this without a fight. I marched to the department manager and asked him straight: how could he give away MY role.

Without hesitation, he simply said that the intern was a “really fun guy.” He even had a pilot’s license and had promised to take the whole team to Las Vegas and show them a really good time.

That’s it.

That’s why after years of hard work, patience, and loyalty, I was passed over for my dream job.

I related this story at the wedding. The woman sitting across from me said something like: “This happened to you? But you are so young.”

She couldn’t understand how this was still happening to women.

She excused herself to go to the bathroom, and I never talked to her again during the rest of the wedding.

She probably had enough of me challenging her worldview.

But it has to be said. Even though women have accomplished great things and won many battles when it comes to professional opportunity, we have not won the war.

I am the first person to admit that my professional journey has been much better than my mother’s. And if I had a daughter, I would like to believe that she would experience an even brighter future.

But we can’t fool ourselves into compliance.

The McKinsey director was punished, and there was universal condemnation of his comments. However, the real goal is to get to a point where we don’t have to.

Should You Trust Your Doubt?

What if the thing you’ve been told is your biggest weakness is actually your greatest advantage? I didn’t believe it either. Then I spent four days in a classroom at Columbia.

The course was called Quantitative Intuition, and it tackled the challenges of decision-making in a world of big data. There is so much information available to us, yet it has not led to better decisions.

I didn’t know what to expect.

I walked in as someone who had spent an entire career being told she asked too many questions and relied too much on instinct. I walked out as someone who learned that both of those things were strengths.

After a career of being told that I ask too many questions, you can imagine my surprise when we started discussing the most powerful tool of decision-making: asking questions.

Specifically, precision questioning. A technique that helps clarify priorities, define outcomes, and identify knowledge gaps.

One of my favorite sayings from the class: “The smartest person in the room asks questions. They do not have the answers.”

I’ve had the misfortune of having worked with some leaders who saw questions as weaknesses or fighting words. I couldn’t ask clarifying questions without being told that I should just know. How? Questioning the viability of any plan was seen as negative and unproductive.

But here it was seen as an essential skill.

And that was day one.

On day two, we discussed the backward approach, where the problem is formulated first.

Decisions usually follow a simple script. The course called out five steps: defining the problem, data discovery, data analysis, insights, and implementation. In that order.

But what if you start at the end? Begin with the desired outcome, figure out what analysis you would need and what data would feed it, and then, and only then, go collect it.

Almost like traveling forward in time. You start with the ultimate outcome and trace back through the possible branches of decisions that got you there. Choose a branch and start your process from that point.

I never thought of problems that way. After being introduced to the concept, I sat in the classroom thinking of all the time wasted looking for data that simply doesn’t matter.

All the reports that no one read. The emails no one opened because they answered questions that no one had asked.

We also talked about guesstimating. I thought guesstimating was a shortcut you used when you didn’t know anything. It’s actually a legitimate technique to operate with limited information.

Rough estimation and back-of-the-envelope calculations to approximate an answer. Not an end result, but a way to move forward when enough data is not available.

In a way, accounting is full of estimation. Non-accountants think that we are strict and that our numbers are set in stone. In reality, so much of our work is guesstimating.

Accruals are nothing but a guesstimate of how much the company earns and owes. There might be contracts, emails, and purchase orders, but at the end of the day, until that invoice or bill is received with a total amount and a due date, we are just guesstimating.

Financial statements are built on that concept. So it can’t be too wrong.

Then we got to biases. The one that hit me hardest was overconfidence. I didn’t think I had a problem with overconfidence… I was wrong.

We did one exercise that truly opened my eyes. We had 10 questions on a sheet of paper. The challenge was to provide ranges that would contain the answer to each question. For example, what is the length of the Nile River (*4,130 miles), and how many books are in the Old Testament (*39).

There was no limit on the ranges. I could have answered zero to infinity for every single question and gotten all 10 right. But I didn’t. Because I was sure I knew better.

A little humility about what I didn’t know would have produced a win.

On day three, we did a simulation.

Teams of five played characters who were climbing Mount Everest. The exercise lasted 90 minutes with five rounds of decisions. In each round, we were given a choice: advance to the next camp on our way to the peak, stay put, or go back. The group had a shared goal of reaching the mountaintop, and each participant had their own personal goals as well.

Some groups prioritized staying together instead of reaching the top. My team, where I played the leader, decided that it was better to split and allow at least some of us to attain our goals. Two team members, the environmentalist and the physician, were left together at an early campground. The remaining three players reached the summit.

Afterwards, I questioned if we made the right decision. We scored the most points, but did we win?

There were no right or wrong answers. Each team took the same information and used it in very different ways and achieved very different results. No different from real life.

And that was the lesson.

On our last day, classmates kept going back to the simulation, highlighting it as their favorite part of the class.

But for me, the best part wasn’t the simulation. It was learning alongside my classmates in real time, watching how the same ideas reached each of us differently.

I think about this class often. Not the frameworks or the vocabulary, though those stayed too. What stayed most was the permission it gave me. Permission to question, to estimate, to act without certainty, and to trust that doubt is not the enemy of good decisions.

It is the beginning of them.

Embrace the Chaos

“Embrace the chaos.”

This was the advice my friend didn’t expect to receive.

She called me asking for help updating her resume and preparing for interviews. She told the story of many toxic workplaces. Vague and ever-changing strategies. Lack of resources. Poor communication. High achievers leaving with their institutional knowledge, and managers whose only competency seemed to be delegating work.

She was done with her job.

To her surprise, my advice was to embrace the chaos instead.

I told her to prepare a vision for how things should be done, with her in charge, and present it to the CFO. After all, what’s the worst thing that could happen? The CFO could simply say no. And in that case, I would help her update her resume and look for another job as planned.

Here’s the thing about chaos: in a well-run organization, every problem already has an owner. There is no gap to fill. In a chaotic one, problems are orphaned. Nobody is in charge of fixing them because nobody has been asked to.

So my friend spent a few weeks documenting what was broken and wrote up a practical plan for how she would fix it. Nothing elaborate. Just a clear assessment and a path forward.

What people forget is that if you hate your job and feel like you are drowning, you are probably not alone. Your colleagues are feeling the same way. So is your boss. So is your boss’s boss. Everyone is waiting for someone to arrive with a plan to fix things.

If you are willing to be that person, to own the mess and bring the plan, you can turn a bad situation into the biggest career opportunity you’ve had.

My friend followed my advice. She got a promotion and a salary increase that would have taken a typical accountant many years to reach.

I would never suggest joining a toxic workplace on purpose. A toxic workplace can burn you out and make you question your own worth. I know from experience. But if you are already working in chaos and can’t leave for whatever reason, don’t just survive it.

Use it.

When Everything is a Priority

In a sea of “tell me about yourself,” someone asked an interesting question at an interview the other day.

The hiring manager asked me how I prioritize when everything is a priority. In this era of doing more with less and fast-moving environments, it is a fair question, and it started a meaningful conversation about how we work. It’s a question most people answer with instinct. There’s a better way.

When prioritizing, I use three pillars: risk, visibility, and materiality.

Risk.

In accounting, there are areas of the financials that have a higher propensity to cause harm if things are missed or not kept under control. Revenue recognition and accruals at reporting period ends are common examples. These areas tend to be the focus of compliance efforts. A useful signal: if an area comes up time and time again during audits, it is probably high risk. The question to ask: what happens if I get this wrong? If the answer scares you, that’s where you start.

Visibility.

Leadership will always have one or two KPIs (Key Performance Indicators) that they track closely while monitoring growth or the lack of it. Maybe it is a metric that once caused a major issue in a senior leader’s career, and they’ve learned to watch it closely ever since. You’ll know what these are quickly. They will be the first or second thing asked about during review meetings. It keeps you from getting caught off guard. When leadership asks, and they will, you need to have the answer. The people who advance prioritize based on what leadership is actually measuring.

Materiality.

Materiality is the accounting concept that only information significant enough to influence stakeholder decisions needs to be highlighted in financial reports. Most companies set a quantitative materiality threshold, a minimum dollar amount that triggers further review or action. If an issue falls below that threshold, it won’t necessarily be ignored, but it won’t be prioritized either. In accounting terms, “it is not material.” This is the pillar that gives you permission to say: this can wait. Most people never give themselves that permission.

These three pillars often overlap. When something is risky, visible, and material, that is where you focus first. No debate needed.

But here is what I find interesting: these are accounting concepts, but the logic behind them applies far beyond accounting.

When choosing what to prioritize in any context, ask yourself: What is the risk of not doing this? Do the people who matter, your team, your boss, your family, consider this important? And will this decision meaningfully change the outcome, or is it noise?

Those three questions can cut through most of the paralysis that comes with competing priorities. Not everything that feels urgent is risky. Not everything that is visible is material. And not everything that is material is visible. Knowing the difference is where good prioritization starts. And in a sea where everything feels urgent, that might be the only thing that keeps you afloat.

Know Your Numbers

Graduation season. Commencement speakers across the country are talking about AI, and how it will change everything. Graduating classes are booing them. They just spent four years and a small fortune preparing for careers they’re now being told might not exist.

I won’t pretend to know what AI will or won’t do to the professional lives of new grads, but I do know what determines whether people make good career decisions or bad ones.

It is not just talent, or timing, or connections. It is whether they are acting from confidence or from fear. And that almost always comes down to money.

At some point, most people will be in a job they hate. And although you can always change jobs, the process can be lengthy and difficult. In the current environment, it might feel downright impossible.

You never want to stay at a job that is affecting your mental or physical health just because rent is due on the first. You don’t want to be pushed into actions that could hurt your professional reputation for years just because you don’t have a single month of savings.

When I talk about a safety net, I don’t mean millions or even hundreds of thousands of dollars. If you understand your numbers and know your burn rate, how much you absolutely need to survive for a period of time, you can act.

Early in my career, I found myself at a job that was toxic. I was not valued and had spent years waiting for a promotion that never came. Worse, the job had started making me question my own worth. A voice in my head started whispering that maybe I wasn’t good enough for that promotion.

I had to leave.

I started looking for another job, but I felt that the toxicity and the long hours were not letting me perform my best at interviews. I needed to leave and cleanse myself of that place. I would not advise this as a first choice, but it was how I felt at the time.

I looked at my numbers and decided that I needed $5,000. This was over 15 years ago. Things were cheaper, and I had a lot fewer bills to pay, but that and some part-time temp work should be enough to get me through six months.

From that point, my focus was on saving that $5,000. Once I had it in the bank, I quit. And things worked out. When I look back, I always see this as the real beginning of my accounting career. A small amount of money and confidence in my numbers made all the difference.

But it is not just about escaping from a bad situation.

A friend recently reached out to me, completely bummed out. A company had contacted him with his dream job. The job he wanted since he was a kid. He loved the company, the mission, the team. The role was a perfect next step and promised a lot of upside. But it came with a 30% pay cut. The company was a startup that couldn’t match his Fortune 10 salary. He was offered equity, but promises of future riches do not pay the bills today.

He looked at his budget and couldn’t figure out how to survive with 30% less. With a heavy heart, he turned it down.

I hope this experience makes my friend take a hard look at his numbers.

Most people don’t think about money as a career tool until the moment they need it to be one. A new job that requires a move. A new opportunity that requires a pay cut. The chance to pursue a dream. All of those require a reserve of money and the clarity to use it.

It all comes down to money. Having cash in the bank gives you freedom. And most importantly, it allows you to act from a place of confidence, not a place of fear.

Ironically, even if you decide to stay at your job, knowing that you could leave changes everything. You speak up more. You walk with more confidence. You hold your convictions more firmly. And that makes you a better leader and a better employee, the kind that good organizations notice and reward.

To new graduates, I still don’t know what AI will do to your careers. But I do know this: learn your numbers. Know what you need. Build a cushion. Everything else gets easier from there.

The Questions That Were Never Asked

I could tell something was wrong the moment my friend picked up the phone. She had just spent a “ton of money” paying someone to rewrite her LinkedIn profile and they had done a terrible job. A bad, no good, horrible job whose only use would be as kindling for a fire (I’m paraphrasing here).

I was surprised since she had used a professional. Let me take a look, I said. Maybe I could help.

The package included a resume, executive bio, and a LinkedIn profile with instructions about how to populate the site. I read it all and thought… it was perfectly okay. It was professional and well written, easy to read, full of the buzzy keywords. I started to wonder what the real problem was.

I decided it was an issue of misaligned goals. I asked my friend some questions to find out.

Questions like: What is the main purpose of this profile? What do you want people to take away when looking at it? What kind of tone do you want to convey? Who is your main audience? Besides company names and titles, what do you want to communicate about your career?

She was surprised by the questions because her LinkedIn profile writer never asked them. But more importantly, she herself had not thought about them. She asked for a couple of days to sit with it.

Once she came back with answers, I had the clarity I needed to do a rewrite. I sent it to her a few days later, and she loved it. This was finally what she wanted. What she wanted all along.

She thanked me for all my hard work. What she didn’t know was how little work I had done. I pretty much changed the point of view and did some surgical rewrites, but overall, the foundation was the same package she had paid for.

This made me think about how many projects and pieces of work get tossed every day because we don’t ask simple questions about the end goal at the beginning. About how we discard good work just because it doesn’t match the fuzzy picture we have in our minds.

The professional who helped my friend never asked about the ultimate goal. She assumed it was the same as everyone’s: maximize recruiter engagement. And she delivered exactly that. A well-put-together yet generic result.

My friend failed to see the potential in what she already had. A few strategic questions and a few precise rewrites were all it took to get to the desired outcome.

Good work gets thrown away every day. Not because it’s wrong, but because nobody asks what “right” is supposed to look like.

I’ve Seen Stuff

And just like that, we are in 2026.

After grad school I started this blog to organize my thoughts and share them with the world. I’ve always had so much in my head that it just made sense.

But then life got busy. I started my career, sometimes working two jobs. Suddenly, there were fewer and fewer hours in the day, so I decided to pause writing. The entire time, I was planning to come back once things calmed down. Well, it is now 2026, 14 years since my last post.

So what have I been doing for 14 years? I got my CPA and built a career in corporate accounting. I’ve worked inside companies whose names you’d recognize, alongside people whose personalities matched the size of the brands. I survived a global pandemic. And recently, I spent a year in a CFO Executive program at Columbia that changed my perspective on a lot of things.

As I told someone at a job interview the other day, “I’ve seen stuff.”

My new goal is to post consistently for the next year. Start with a goal, build a habit.

Still, as I revisit my old posts, I realize that my thoughts have not changed much. I have more nuanced opinions on a couple of things, but overall, I still stand by everything I wrote back in the day.

I don’t know if that is good or bad. On one side, it shows conviction and consistency. On the other, it might show inflexibility. After everything I’ve done, you would think my thinking would have evolved more. Adam Grant, author of Think Again and a big proponent of rethinking your assumptions, would probably disapprove. But I’d rather be honest about where I stand than pretend 14 years turned me into a different person.

Let’s restart this journey and see where it takes us.