I’ve been having a recurring conversation lately. Different cities, different conference rooms, different names on business cards. Same anxiety underneath.
The (mostly) men I’m meeting are in their 50s and early 60s. They’ve built real things. They run real companies. They sit at the tops of decision trees in organisations that matter to this economy. And when I steer the conversation toward the new generation of self-taught digital workers, something shifts. The posture changes. The vocabulary gets defensive. They are visibly tense.
“These kids are beating the system”. Hold my glass. I’ve heard that phrase, or some version of it, more times than I can count. And every time I hear it, I think: this is what fear dressed up as principle sounds like. Because the kids aren’t beating the system. They exited it. Quietly, methodically, without asking anyone’s permission. And they built something better for themselves on the other side. Which the current generation of executives couldn’t.
Let me name them properly. I’m calling them Bypasspreneurs. Pakistani coders, analysts, designers, marketers and micro entrepreneurs who bypassed the legacy education-to-employment conveyor belt, bypassed the compressed local salary bands, bypassed the slow internal hierarchies and the gatekeepers who guard them. They connected directly with global clients willing to pay global rates. In the first eleven months of FY2026 alone, freelancers generated over a billion dollars in IT-related export earnings. Total IT and IT-enabled services exports are tracking above $4.18 billion for the year. This is a structural shift in how Pakistan generates foreign exchange, and it happened largely without institutional help and certainly without the blessing of the executive class now complaining about it.
So what exactly is the complaint? It comes in three flavours. First, the tax grievance: everyone should be treated equally; the preferential regime for freelancers is unfair; bad actors are abusing it. Second, the hiring frustration: we cannot find good people in software, analytics, finance and marketing because the best ones have gone independent. Third, the unspoken one: we didn’t train these people, we didn’t credential them, and yet they’re outearning our mid-level managers and threatening to outpace us entirely.
What I find stunning is not that these concerns exist but that they are the dominant response. No curiosity about what created this cohort. No reckoning with decades of elite capture in education and credentialing that made these alternative pathways necessary. No serious engagement with the macroeconomic signal that foreign buyers are willingly paying premium rates for Pakistani output. Just: tax them. Regulate this back into a shape we recognise. That is institutional self-preservation wearing the clothes of policy.
And here is the part worth sitting with. I compiled the names and estimated ages of 50 CEOs running Pakistan’s largest banks, PSX-listed companies, and private conglomerates. The average age is 58. Thirty-six of the fifty are 55 or older. Seventeen are past 60. Only a handful are in their 40s, and those are mostly multinational appointees rotating through or next-generation family successors, not people who climbed through Pakistani institutional structures.
The men setting policy, lobbying tax authorities, and controlling the hiring decisions overwhelmingly began their careers in the early 1980s, in a world of paper files and relationship banking, and are now making decisions about a generation that taught itself everything from YouTube and a laptop and has already sold that skill to buyers in New York, Dubai and London.
These same executives, by their own admission, mostly use AI to generate summaries, draft reports and run basic research. The generation they are trying to contain has moved past that. The Bypasspreneurs use AI to redesign workflows, build client-facing tools, and run lean operations across time zones. They are compounding capability at a pace traditional structures are not built to absorb. The gap is widening every quarter – and the people with the institutional power to close it are spending their energy trying to tax it instead.
Pakistan cannot afford this standoff. So let me be direct about what the corporate leadership class actually needs to do. Not aspirationally but concretely.
PSX 100 companies, large family-owned conglomerates and banks: stop treating Bypasspreneurs as a tax problem and start treating them as your most valuable external resource. Commission them for the hard work, not the easy work. If you run a listed company or a Seth-owned business with real institutional weight, stop using independent digital talent for low-stakes, low-pay tasks while shielding your permanent structures from scrutiny.
Bring Bypasspreneurs in to pressure test your core workflows against AI-augmented alternatives. Have them build internal decision support tools your own teams lack the fluency to build. Have them audit functions protected by hierarchy rather than performance. Pay them at global rates. Anything less signals bad faith and accelerates talent flight offshore. And do not lecture them on what to build or why your problem is uniquely hard. Get past that.
Stop trying to own them and learn to engage them instead. The old compact, predictable progression within a hierarchy in exchange for loyalty is not what high-agency talent wants and not what the market rewards. Build outcome-based engagement: project-specific mandates with clear deliverables, guild-style collaborations, lightweight venture arrangements where both sides have skin in the game. In software, analytics and strategy, where your hiring has already broken down, run structured pilots that pair your institutional knowledge with their digital agility. The objective is not mass conversion to employment. It is to capture output and momentum while they continue serving global demand and bring that knowledge back in.
Banks specifically: the Bypasspreneurs have a payment infrastructure problem you have the power to solve. Foreign remittances from freelance earnings flow through friction-heavy channels. That is not a compliance headache to avoid. It is a deposit base, a transaction volume and a relationship opportunity sitting uncaptured. Build the rails before they route permanently around the formal system.
Use your political leverage publicly and specifically. The 0.25 per cent final tax regime for genuine IT exporters was extended to 2029. Stop quietly lobbying against it while complaining about bad actors at dinner. Defend the regime. Separately and precisely, back enforcement against abuse. Those are two different arguments and conflating them is intellectually dishonest.
Install reverse mentorship as a board-level practice, not a PR exercise. Every CEO should have recurring exposure to someone operating at the frontier of what global clients buy and what applied AI does in production. A real relationship, repeated, with accountability both ways. This is the only honest way to close the knowledge gap driving both the fear and the bad policy.
Finally, redefine what you are optimising for. Most boardroom conversations are still about defending organisational position. The required shift is towards Pakistan’s total digital exports. When a policy shrinks the overall pie to protect a slice, name it as that. Do not dress it up as fairness.
The Bypasspreneurs did not wait for the system to be ready. They assessed what it could offer, found it insufficient, and built their own pathways. That is not ingratitude. That is rationality.
The executives I’ve met built real things under genuinely difficult conditions. The anxiety is not manufactured. Plateauing in what should be your strongest professional decade, while a self-trained generation using YouTube moves faster than your organisation can adapt, is hard. But park the ego, get out of the ‘I know better’ mode and embrace the opportunity.
Difficulty does not make the defensive posture strategic. It makes it understandable and still wrong. History will not record the precise tax percentages debated in these boardrooms. It will record who expanded Pakistan’s digital frontier and who tried to regulate it from behind a desk. The Bypasspreneurs already made their choice. The question for the corner office class is whether they use the platform, capital, and networks they still hold to walk alongside this generation or spend their remaining influence trying to slow it down.
The choice is entirely theirs. So are the consequences.
The writer is a strategist focused on digital transformation in emerging markets. He tweets/posts@faizansiddiqi and blogs at: blog.chinookstrategy.com
