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.

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.

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.