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.

The Math is Not Mathing

Accounting Manager is the single worst job in accounting.

That was my comment on someone else’s LinkedIn post about what Accounting Managers do. It received thousands of impressions. Apparently, I’m not alone in my belief.

What I didn’t say in that comment is why. Not just why the job is bad, but why it matters. Because the damage isn’t limited to the people in the role. It reaches everyone around them.

There is a concept in organizational development called the Leadership Pipeline. The idea is simple: manager roles are linchpin positions. Without them, organizations can’t sustain themselves long-term.

The literature is clear that the most difficult career transition is the one from Managing the Self to Managing Others. The people who get promoted are the ones with the strongest technical skills. The ones with the interpersonal and relationship skills needed to succeed as a manager get left behind. What makes you good at the first job is not what makes you good at the next one.

Still, this is not an insurmountable obstacle. Training can go a long way.

But of course, that’s where the real failure happens.

I remember being a first-time manager and having my Director reprimand me for scheduling too many training sessions with my team. They should know, she would say. My response: how? Who taught them?

She didn’t have an answer because there wasn’t one. Nobody had taught them. Nobody had taught me either. The company expected people to become managers overnight and then blamed them when they struggled. The training budget was zero. The patience was less than that.

A less experienced person would have taken that feedback and stopped the sessions. I doubled down.

But most new managers don’t push back. They absorb the message: training is a waste of time, your team should already know, figure it out. And then they spend the next several years managing by instinct instead of by skill, burning out, and wondering why the job feels impossible.

Over the years, I’ve had friends take steps back in their careers because they didn’t want to ‘babysit’ a team. I’ve never liked that comparison, but I understand where it comes from. When you’re given a team with no training on how to lead them, managing starts to feel like supervising instead of leading.

But here’s what people miss: the team feels it too. Nobody wants to be managed by someone who is clearly overwhelmed, clearly untrained, and clearly just trying to survive until the next close. Reports can tell the difference between a leader who is developing them and a manager who is just keeping track of them. When both sides feel like the relationship is broken, it transforms from a people problem to a design problem.

And the math confirms it. The increase in pay from individual contributor to manager is rarely proportional to the increase in stress and responsibility. You take on twice the workload, lose your overtime eligibility, become accountable for other people’s output, and get a raise that barely covers the difference. The math is not mathing.

This is the first consequence that people feel in their careers, long before the pipeline runs dry. The job stops being worth it.

And young people have noticed.

A little more than a year ago, I was having lunch with a group of junior and staff accountants  from another team. The conversation turned to the career ladder, and every single young person at the table said they didn’t want to ever become managers.

They saw their own manager and thought: too much work for not enough money.

Gen Z is choosing to stay in individual contributor roles. The more entrepreneurial ones are pursuing side hustles and their own path. The famous 5-9 after their 9-5.

They are not wrong.

The real question is what happens 10 years from now when there isn’t a pipeline of experienced managers who know how to build and lead a team. What happens when we forget how to get things done through others? What awaits us when the institutional knowledge of how to develop people, run a close with a team of varying skill levels, and turn a group of individuals into a functioning unit has simply disappeared because nobody wanted the job?

The optimist in me thinks that when faced with that crisis, companies will finally invest in real managerial training and build compensation structures that make the role worth taking.

The pessimist in me looks at current leadership, at how they’re letting things deteriorate in real time, and thinks that by the time anyone notices the pipeline is empty, it will already be too late to fill it. And when that happens, we won’t just be missing managers. We’ll be missing the people who know how to fix the problem.

The Worst Job in Accounting

Believe it or not, becoming an accounting manager was aspirational when I started out.

Being a manager meant making more money, having more freedom and flexibility, and having real power and autonomy. There used to be a clear distinction between managers and working managers. Managers oversaw teams: onboarding, training, reviewing, and assigning work. Working managers did all of that plus carried a full load of their own deliverables.

That distinction no longer exists. Now all managers are working managers, juggling workloads sometimes heavier than their direct reports’ while also being expected to manage their teams in their downtime.

Devaluing the title destroyed what made the job aspirational.

The worst part is that we did it on purpose.

In a recent episode of the Optimist Economy podcast (recommended listen), titled “No Overtime for the Supervisor of Sandwiches,” economist Kathryn Anne Edwards discusses overtime. Midway through, my ears perked up. She puts words to something I’ve observed for years but couldn’t quite articulate.

Edwards discusses how in 2004 Congress raised the salary cap for overtime eligibility. In response, businesses did what she calls the “systematic managerial titling of workers.” To avoid paying overtime, companies took employees who had just become eligible and gave them managerial titles. Managers are exempt. Problem solved. One of the most outrageous examples: hostesses becoming Directors of First Impressions.

I am not an economist, but this clarifies so much of what I’ve seen in my career.

Early in my career, I reached a breaking point waiting for a promotion. I was ready to quit when the company’s CFO called me to his office. He argued that the problem was not the lack of a promotion, but my attachment to a title. His words: we all know what you do for this company and we value it, so what does it matter what your title is?

I looked at the nameplate on his desk. It read: Cofounder / Chief Financial Officer.

I said: so we can change that to Janitor, and you wouldn’t mind, right? I mean, we all know this company wouldn’t be what it is without you.

He paused. Then he smiled. You’re right, he said.

Titles matter. They matter to the people doing the work. They matter when you’re looking for your next opportunity. A title is one of the few data points a potential employer uses to understand the scope of what you did. And it matters on the other side too: when a candidate evaluates a role, the title is how they gauge what the job is and what fair compensation should look like.

By overusing and outright abusing managerial titles, companies broke the compass. Accounting Manager has become the single worst job in accounting.

And things are getting worse.

In recent months, recruiters keep reaching out to me about Accounting Manager and Senior Accounting Manager roles. Their opening line is always the same: this role is expected to run the entire accounting function.

They outline the responsibilities. I listen. Then I let them know that what they’re describing is a Controller, not a Manager, and I advise them to go back to their hiring team and rethink the title and the compensation package.

The title inflation that started as a way to avoid paying overtime has now become something else entirely. It’s a way to get senior-level work at mid-level prices. That’s not a broken system. That’s the system working exactly as designed.

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.

That’s Why You Hired Me

Another CEO declares middle management dead. Flat organizations are hailed as a corporate utopia full of efficiencies and cost savings.

I understand why this dream appeals to people who have survived bad middle managers. But as someone who has been a middle manager, I can confidently say that middle managers are the heart of most organizations.

They operationalize the vision of leadership.

VPs and other C-suite executives come up with dazzling ideas. It is up to the middle managers to make them a reality. No VP that I know will sit with a team to make the small go/no-go decisions. Whether a variance is worth flagging or just noise, how to code a transaction that spans two entities, which reconciling items to escalate and which to resolve on the spot. These might seem like small decisions, but they are the decisions that can paralyze a team and stop progress.

I remember one occasion when I received a request from corporate. They wanted my team to document some processes. I had a team of four, and each one had a task or two to document. I sent the team the request from corporate and asked them to start working on it as soon as close was over. I sent two separate reminders, yet I grew concerned when no one reached out with questions. In my book, no questions mean no work.

A few days before the deadline, I set up an in-office 20-minute meeting to go over the progress and answer any questions. My boss pushed back. He said: why do you need a meeting? You sent clear instructions. This is a no-brainer. I said: just trust me.

At the meeting we found out that no one had even started working on the project. I was proven right.

One person didn’t even know there was a project to work on. He asked if he was cc’d on the emails. He was. The second one received the emails but didn’t think they applied to him. His thought: if I had to do something, someone would tell me in person. The third one knew about the project but somehow confused the deadline date with the date he was supposed to start. The fourth one understood the assignment but had not done anything about it… yet.

After the meeting my boss asked me to stay behind. His exact words were: what the f* was that? He couldn’t understand how this group of people had not understood the assignment.

I responded: that’s why you hired me.

Someone might respond to this story with: you just had a bad team. Hire better people. To that I say: I hired the best team I could afford.

Good talent is expensive, and most companies are not willing to write a blank check. But even if your company is willing to pay top dollar to hire self-directed talent, where do you think that talent came from? The best professionals I know had great middle managers showing them the ropes for years. Giving them feedback and helping them along the way.

Leaders are built, not born.

A friend of mine started at the bottom and retired from the C-suite. At 65, she still credits her first two bosses for the trajectory.

So you’re a deep-pocketed company that decided to outsource the development of its people to other companies and only hire the best and brightest. I ask you: how long before the best and brightest get tired of self-directing and going above and beyond without any room to grow?

Imagine you have a team member who takes it upon themselves to onboard new hires and resolve ambiguity for the group. This person is already doing the work of a middle manager. They’re just not being paid for it, titled for it, or given anywhere to go because of it. How long before they figure that out? The distance between an individual contributor and the C-suite is too wide to cross without steps in between. Unless you have a top-notch internal leadership program that can bridge that gap, your best people will leave to get the growth they can’t get at your company.

I met someone recently whose company had removed all middle managers. He proudly said that it had been a year without any measurable loss of productivity. And I believe him.

But what will your productivity be in three to five years?

I do believe that if you have a strong team, probably built by a strong middle manager, where everyone knows what they do and there is cohesion, you can remove that middle manager without much change. At first.

Things start to shift once the team changes. People leave. People get hired. The strategy changes. But someone has to handle the next new executive ask.

That’s when the team starts to suffer. That’s when the bottom line suffers. That’s when you feel the absence of the middle manager. Another CEO can declare them dead. But they’re the ones keeping the company alive.

Impossible Questions

I knew better, but I did it anyway. I clicked on a clickbait article about hiring red flags.

Some of the advice was basic. Never hire someone who badmouths their former employer. Never hire someone who asks no questions. Never hire someone who doesn’t show curiosity about the company or the role. Fair enough.

But there was one that didn’t sit well with me. The author argued that you should never hire someone who can’t answer the question: “Tell me about your biggest failure.”

The argument was that someone who couldn’t answer this question didn’t have enough self-awareness to be a good performer.

I disagree.

Not because this is untrue, but because this is what I call an impossible question.

If you answer truthfully, you are highlighting your shortcomings to the hiring manager. And you don’t know what that manager considers a disqualifier. You try something relatively safe, only to find out you’re sitting across from someone who sees that particular issue as unforgivable.

If on the other hand you try to be strategic and answer with a non-answer, or a strength disguised as a weakness, you look disingenuous. Your application moves to the rejection pile.

Heads you lose, tails you also lose.

People know what their biggest failures are. They probably lie awake at night reliving every moment. They just won’t tell you. It’s not a lack of self-awareness. It’s self-preservation.

“What is your biggest weakness” is another question in this category. It gets asked less and less these days because people have realized it doesn’t tell you anything about a candidate’s ability; other than their storytelling and spin abilities.

By asking impossible questions, interviewers aren’t being clever or fishing for red flags. They are setting people up for failure.

And the interview process doesn’t need more help at being terrible. It’s already broken and getting worse by the minute, with algorithms removing qualified candidates automatically and recruiters who can’t be bothered to close the loop after taking up someone’s time for weeks.

As interviewers, we can do better. Ask what the candidate has built. Ask how they think through problems. Ask what they would do in the first 90 days. Those questions tell you something real.

Or better yet, ask them to ask you questions. See how they think and what they care about. That will tell you more in five minutes than any rehearsed failure story ever will.

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.

Fire 30% and Call It Innovation

The interview was going well until it wasn’t.

I was sitting across from a VP who was clearly proud of the company’s multi-year financial transformation project. They were upgrading the ERP (Enterprise Resource Planning) system and adding new tools, including some with AI functionality. It all sounded exciting, and I told her so.

This is when the tone of the conversation changed.

She said that the downside of it all was that six months after go-live, whoever got this position (I was interviewing for a Controller position) was going to have to let go of 30% of the accounting department. I asked where these metrics came from.

A 30% layoff in six months seemed extreme to me.

From her response, it became clear that there was nothing behind the number, just the familiar logic that technology should always mean fewer people. She assumed six months was enough time to work out all the bugs after implementation, and that 30% seemed like a big, round number that would show a nice return on the project investment.

I pushed back. In my experience, automation implementations don’t lead to less work. Yes, the simple repetitive tasks go away, but they get replaced with review and control work. Plus, accounting always has a long list of “nice to haves” that can now be addressed.

The VP didn’t seem to like being challenged. She argued that even if the work didn’t go away, I would still have to fire people and replace them with others who had the “right skill sets.”

I challenged her again: “Why don’t we simply upskill the current staff?” It would be easier, and cheaper, since those people already understood the business and the workflows.

She didn’t have a response and quickly changed the subject. She got off the Zoom shortly after, and I knew I was not going to get this job.

And I was okay with it. This was clearly not a company run by executives who value their people.

To quote Ethan Mollick, almost no one is showing any ‘imagination’ when it comes to what AI could actually build.

Business leaders are almost exclusively focused on how AI can help them lower costs by replacing humans. Reducing headcount is the oldest and most basic way to make your numbers look better for a few quarters. But it doesn’t create a foundation for growth.

Why aren’t leaders focused on doing more? Going into new businesses. Creating entirely new categories. Helping their people become capable of work that didn’t exist two years ago. The VP I interviewed with had a chance to build something. She had a team that already knew the business. She could have invested in them. She chose to cut instead.

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.