Hi, I’m Drew Monti, a technologist and entrepreneur. ‘Wisdom’ is a series of posts about my journey building a business and transforming my life through entrepreneurship. I’ll be chipping away at old ideas and sharing the lessons I’ve learned along the way. I hope it’s as useful to you as it is fun for me to write.
tl;dr: Sell like your life depends on it—because it does.
The biggest handicap a formal education left me with was not knowing how to sell.
I was taught:
- Get good grades.
- Get into the best programmes.
- Become the best in your field: companies will line up to hire you, you’ll get rich doing what you love, and sky will be your only limit.
Many of us received similar advice from well-intentioned parents and teachers, along with other mantras like “follow your passions” and “hard work pays off”. Bless them and the world they grew up in.
All this wisdom turned out to be not only blatantly outdated but actively impairing.
The reason is simple: in an age where the traditional social contract between employers and employees has broken down—where simply showing up and doing your job well no longer guarantees career safety or advancement—this roadmap leaves your professional future entirely in the hands of others.
Do you want to be safe, or do you want to be free?
In my first job, eager to prove myself, I joined a large firm for the explicit reason to work on the sort of large-scale, big-budget, cutting-edge projects that would make the most of my hard-earned skills. I was baffled to realise that all my work consisted exclusively in following orders from the management, doing mindless tasks a teenager could handle—a far cry from the gruelling hiring process and the big talk of “we only hire the best for the hardest work on earth”. What the fuck was that?
Within months, I felt like my career had already hit a dead end. I knew I needed a whole other sort of projects in order to grow professionally. But—working for a big brand came with the message that moving around was CV suicide, and that patience and playing the game were the key to success. After all, that’s what I had been taught. “What do you know about how the world works? Don’t be arrogant. Don’t be entitled. Be patient. Be humble. Your turn will come. Rome wasn’t build in a day. Be happy that you have a well-paying full-time job at a prestigious firm“, the voices in my head kept saying.
So, I ended up staying for three years.
During that period, nothing changed. I kept proactive, working harder, faster, and longer than anyone else, just as I’d been taught was essential for success. All while being patient and repeating to myself “Rome wasn’t build in a day. You’re just working your way up. Keep at it. This will pay off”.
And then it finally dawned on me: careers don’t work the way I was taught. The better you are at what you do, the bigger the incentive to keep you exactly where you are. I was shocked. I had been blindly applying old widsom to a new world.
This was the first of many realisations that, over the next decade, led me to distance myself entirely from institutional careers.
For those of us who grew up believing that joining a prestigious institution—a corporation, a university, the government—would allow us to climb the ranks through raw talent and grit, it’s often completely impossible to imagine alternative routes to professional fulfilment. You want to be an investment banker, the world’s best ballerina, an astronaut—but you don’t want your career to depend on others? So what—do you start your own bank? Your own theatre? Your space agency?
I’m not saying it’s simple. I’m saying it’s possible. And it starts with shifting your mindset.
You are a product (like it or not)
Without knowing how to sell yourself directly to the end user of your trade, your entire professional life reduces to hitching rides and being a guest on somebody else’s car—no matter how luxurious the seat.
It’s the personal counterpart to the “engineer’s fallacy” – I was taught that great employees sell like hotcakes, just like great products sell themselves. It’s a comforting narrative, but neither is true.
Selling is like hunting—it’s what brings food to the table. That’s why, in many companies, salespeople are the highest-paid employees and the first to be paid, even though they generally aren’t the sharpest tools in the box.
Not knowing how to sell is the equivalent of not knowing how to hunt prey or start a fire if you’re stranded in the wilderness—you just won’t survive. If you can’t provide for yourself, no matter how talented you are, your survival depends on those who can. They are higher up in the food chain and you dance to their tune.
Are you a butcher or a hunter?
Now, an important point. You might be confused whether by “selling” I mean knowing how to land a job at Goldman Sachs on your first interview, knowing how to sell a pen to Jordan Belfort, or something else. In this context, selling means one of three things:
- Selling your services to an employer
- Selling someone else’s services to a client
- Selling your services to a client
The above differ only in terms of what is being sold and in your proximity to the end user (aka to money). Going back to the hunting metaphor:
- You’re a non-sales employee—you process food
- You’re a salesperson—you hunt for food
- You’re a business owner or a freelancer—you hunt and process food
It’s not about whether you want to sell or not. You can choose not to focus on sales as your core expertise, but regardless of your background, you still need to sell. Selling is essential no matter your skillset.
Whether you’re a banker or a dentist, you only have two choices:
- Sell directly to the end user.
- Sell your skills to an intermediary who provides you with a fully-converted, paying customer.
This is a crucial distinction. Have you ever considered that your “proximity to the source” might be as crucial to your career satisfaction as the specific field you’ve chosen? In other words, that how you do it might be just as important as what you do?
Sales as the stepping stone to freedom
For years, I believed that showcasing my competence and grit to employers was all I needed to land my dream job.
Culture didn’t help. From a young age, I was taught that selling was inherently dishonest—an immoral shortcut taken by those looking to “skip the queue” in life and avoid doing the hard work. I equated salespeople with con artists. I wondered why anyone would push something on me; the idea felt cringeworthy. If I needed it, I’d find it myself.
Fast forward, and I found that landing my dream job didn’t significantly change my professional fate. Working hard and being technically excellent — the very qualities I was taught would cement my position in life — meant nothing compared to random political decisions way above me and the ability to just bring in more business. I was a top-notch specialist in a high-paying corporate job, with zero control over my career. My only choice was to keep switching employers.
How could I get out of there? Well, I decided to start a business, but in hindsight, I wouldn’t do it the same way. I lacked some core skills, which I had to learn the hard way at great personal cost. Today, I would approach my exit differently.
I didn’t realise it then, but the first and most important skill you need to master when breaking out of the pack is the ability to sell directly to customers. You need to hunt and cook your own food — no matter if the prey is small and the cuisine is lacking.
You need to start developing these skills as soon as possible. For most of you, A LOT of the effort will be about overcoming discomfort. I know. I’ve been in your shoes. Cold calling. Cold emailing. Leafleting in silly costumes. Door knocking. Posting on shitty social media threads. Joining random meetup events. It’s all part of the ride — embrace it with curiosity and a little silliness, not with pity or self-judgement.
Pro tip: If you are struggling, get a coach – that’s why I’m here 😉
Letting go of narratives
I’ll repeat it once more: as long as your core expertise is technical in nature and you don’t know how to sell it directly to paying customers, you’ll always be at the mercy of intermediaries—nothing but a guest on somebody else’s journey.
No amount of technical proficiency can save you from this. When things are going well in your career, you might get the illusion that being great at what you do is all it takes. It’s not. Don’t be fooled.
Some of you may not care. For the longest of time, I didn’t either. There’s nothing inherently wrong with choosing material comfort and financial stability over meaning and agency, for a period or for the long run. Some may even be lucky enough to have it all. Every journey is unique.
For me, through my twenties and thirties, I learned that creative freedom, control over my time, and the ability to take swift and decisive action matter more than comfort and status.
This wasn’t a sudden realisation; it was a gradual and painful process. Letting go of your former self and of outdated ideas about the world is hard.
So if you want to take control of your career, learn to sell soon and do it like your life depends on it – because it does.
Want to chat about it? Drop me a line.