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Next level: Are you ready to be your own boss?
Quitting your 9-5 to become your own boss sounds like the dream. But managing yourself involves a different kind of grind
Goodbye, appraisal season. It made us question the 9-to-5. It made us reassess the possibility of another year of spreadsheets, Microsoft Teams pings, and a micromanaging boss. We’re now counting the peanuts and wondering if the salary hike even covers a shampoo upgrade. This is the time of the year when most corporate drones start to fantasise about a different life. One that lets us hold the reins, become a baker, a work-from-anywhere writer, a yoga guru. Could we start a company, like Soham-from-college (who wasn’t even that smart) did?
If Soham can, so can you. But before you rage-quit, here’s what to ask yourself.
Am I (sort of) ready? There’s no single way to go solo. Some people plan their exit while still employed, lining up clients, testing out a side-hustle, zeroing on the best freelancing websites, and building a financial cushion on the side. Others prefer the quit-on-the-spot, burn-all-bridges strategy. “Neither is wrong,” says leadership and executive coach Isabel Perez Porras, from Pune. “Ask yourself: Do you need a safety net, or do you thrive on the adrenaline of full commitment?”
Can I afford this life? Figure out what it takes to just stay alive every month. This includes your lifestyle expenses, taxes, insurance and other perks your job quietly paid for. “Save six-to-12 months of living costs before you take the leap,” says Tanvi Shah, a banking and finance lawyer. And face up to your relationship with financial risk, and save accordingly. Most financial planners recommend having another six-months’ worth of savings for dry spells, delayed payments, and surprise bills. And work out what the market rate is for what you plan to charge for your services – you’ll know exactly how much or how little a good month will bring.
Can I do it all (without crying)? Congrats, being your own boss means you’re also your accountant, marketing head, and HR. And oh, you’ll also need to handle legal stuff, like contracts with clients, suppliers, and partners. “Even the smallest setup needs a formal structure,” says Manasi Chatpalliwar, managing partner, Utkarsh Associates, a full service boutique law firm, in Delhi. If you’re building a brand, name, or logo, get it legally registered to protect your identity and work.” Legal, financial, even digital assistance costs money. But work out what can be outsourced to AI and what needs expert input, says Porras.
Will I be a good boss (to myself)? No HR. No clocking out. No boundaries. Going solo can feel like freedom, until you realise you haven’t seen daylight in four days. Have a clear idea of why you want to go solo. For more flexibility? Creative control? Time to play with your dog? Hold on to your why, or you’ll end up being a harsher boss to yourself than your last one. “Rest is productive too,” Porras points out.
Am I ready for the lonely bits? At first, working in your pyjamas with your cat sounds like a dream. But isolation is real. “Find your people,” says Porras. Join mastermind groups, also hit co-working spaces and cafes. Find a mentor in your field to vent to and learn from. The right network can mean less loneliness, more leads, and fewer rookie mistakes.
From HT Brunch, May 31, 2025
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