The Grey Zone

I spent over 12 years in B2B SaaS roles, predominantly in sales, before coming to Proakatemia. Now I’m part of Arole, a team company of 15 people, and I’m learning to build a business instead of just selling one. This semester I had a chance to read three books: Careless People by Sarah Wynn-Williams (2025), half of The Art of War by Sun Tzu (ca. 5th century B.C.E./2001) and the first chapter of Atomic Habits by James Clear (2018).

Three very different books. What connected them for me was the grey zone: the place where things aren’t clearly right or wrong, won or lost, working or not.

The Power and the line that fades

Careless People shows how power can make people feel unaccountable and untouchable. The leaders in the book act as if the rules don’t apply to them, because for a long time nothing happens when they break them (Wynn-Williams, 2025). At first I enjoyed the book, but that changed as she described how she was treated, how decisions were or weren’t made, how morally corrupt Facebook’s leadership was about its role in the US election, what happened in Myanmar, and how ads were emotionally targeted at teenagers (Wynn-Williams, 2025). She noticed the unsettling things early, and she stayed for seven years. She was part of that reckless world too.

Her story made me ask: how far is far enough? How long do you try to fix the things you can fix, and what price are you willing to pay? Is it your mental health, inner peace, your family time, your relationships, or just your sense of who you are?

During COVID, when we were all working from home, my sales director called me on my cellphone out of the blue, which was odd because we used Slack for everything. He told me I would receive commission for a sale I hadn’t made, and that I should send the money back to his personal bank account. Sales directors didn’t get commission on individual deals; they were paid on the target their whole team reached. So this was a way to take money he wasn’t entitled to, through me. It felt shady. On the company’s books, the commission would be mine for an account I never closed or worked on, and I was responsible for every account I closed, from payment and implementation to onboarding and making sure it didn’t churn. But how could I say no to my director? He approved my edge cases, decided my raises and promotions, and thought highly of my work ethic. He also had the power to make my job a living hell.

More than my job security, I was worried that my name would now be on a customer account I had never worked with. I spent a few days thinking it over and talked to my team lead. His reaction surprised me. To him it was normal; others had done the same thing when the director asked. That made me more anxious. If others had done it, maybe I should too. But it still felt like I was part of something that wasn’t a standard process and wasn’t black or white. I was in a grey zone.
After a lot of deliberation, I called my CEO and told him what had happened. It could go either way. My director was close to the CEO and the rest of the leadership, and speaking up could put my job and everything I’d worked for at risk. The CEO asked me to do what the director said and keep a record of the transfer. I did, and then I waited. The lockdown made it worse; in an office I could have just walked over and talked to someone. A few days later the CEO called to tell me they had let the director go. My name was never mentioned, and the director left without making a scene. A man earning $4,000 a month in base salary + few thousands in sales commission lost his job over a few hundred dollars.

Looking back, I’m amazed I made that choice. I kept thinking about the ripple effect: a dad of two lost his job for something he had been doing with everyone else, until he asked me. Decisions like that carry risk, and you live with the consequences. In my case, they turned out in my favour. People praised me, but more importantly they understood something about me: I don’t make under-the-table deals, and I don’t bend rules. The CEO played a big part in that. He stood by the right choice and gave me the safety I needed.

That’s where I relate to Wynn-Williams at a much smaller scale. You can see the problem clearly and still be part of it but speaking up about it is what kept it from becoming a regular problem for me (because I had the leadership without being morally corrupt).

The fight you don’t have to fight

The best fight is the one you didn’t have to fight. But before you go into any fight, you need a clear understanding of yourself. That means no biases and no assumptions about your own strengths. Most of us have been in a situation, a deal or an argument where we knew it was a 50/50 chance. Sun Tzu’s point is that you don’t leave it to chance. You remove that 50/50 by knowing yourself first, and then your enemy (Sun Tzu, ca. 5th century B.C.E./2001).

As an Account Executive, I worked with a dozen big names and knew how they thought. But I didn’t know Etihad Airways. So before going out into the open field with them, my generals, my associates and I deliberated internally. We worked out their pains and gaps, how they were different from our other customers, and what we needed to do to meet their needs. In sales, the “enemy” isn’t the customer. It’s the objections, the doubts and the surprises after the contract is signed. Over 14 months of sales cycle, we went through the whole software with them, including what it couldn’t do. I didn’t hide the weaknesses. We discussed each one openly and found workarounds together.

Sales has a reputation for selling snake oil and getting away with it. I never saw it that way. I was never into overpromising; I focused on my customers’ success, because that’s what led to mine. The deal became one of the biggest of my career and took me to President’s Club in Dubai. But the real win was the trust. Being transparent upfront meant there was no fight later. That’s the fight I didn’t have to fight.

Systems before results

The first chapter of Atomic Habits makes a simple point: small habits compound into big changes, and 1% improvements in overlooked areas show real results in the long run (Clear, 2018). J. Clear separates goals from systems. Goals are the results you want. The system is the process that gets you there.

Things in this world tend to exist in one of two states, order or chaos, and you’d like to think you can simply decide which one you live in. If only it were that easy. Bad habits are a kind of chaos, and moving from chaos back to order takes a lot of energy, while sliding into bad habits takes almost none. You might come home every day, do the dishes, wash the laundry and fold it, but it’s so much easier to throw your dirty clothes on the floor, leave the dishes for the next morning and go straight to bed. That’s entropy at work: when nothing holds things together, they naturally drift toward chaos. Bad habits don’t ask much of you, but good habits ask for effort every single day. Good habits take time, and effects don’t show much at first. J. Clear calls that stretch the valley of disappointment (Clear, 2018). You put in effort, nothing seems to happen, and it’s easy to quit.

We want to build something great with Arole, not just a business but a system for building it. It’s going to take a lot of effort. Our SEO project is in that valley right now. My work is the groundwork. I’m warming up mailboxes, building outreach workflows, writing templates and strategies, and cross-checking the processes with my project team members. None of this brings in a customer yet. Some days it feels like I’m only preparing to start, or still putting the clothes in the laundry. SEO itself works the same way, since rankings take months to move.
There’s a thought I keep coming back to on those days, and it doesn’t come from a business book. It comes from physics. The law of conservation of energy states that energy cannot be created or destroyed, but only transformed. So I like to think the energy I put into habits and systems now doesn’t disappear. It turns into the results later. A warmed-up mailbox is one example. Nobody sees it, but without it every email we send lands in spam.

Reinforcement

When I started writing this essay, I thought the moment I called my CEO was the bravest thing I had done, almost out of character. Looking back at all three stories together, I don’t think it was. Standing up against something wrong has become a habit for me, and it comes from protecting my integrity and my inner peace. I never over promised to Etihad, I worried more about a customer I had never served than about my own paycheck, and I have always cared about what my name is attached to. That wasn’t courage showing up out of nowhere. It was a system I had been building for 12 years without calling it one, and when I ended up in the grey zone, that system is what I fell back on. I’ve also learned that I’m a deliberator. I take days to decide, months to close a deal, and I’m comfortable doing groundwork long before any results show. It makes the waiting harder, and that’s where my anxiety lives, but it’s also why I rarely walk into a fight unprepared. I’m learning to trust that slowness instead of fighting it.