We Need to Talk About Bruno – Wait, I Mean Money – before You Quit
This week, I spent a ridiculous amount of time chasing invoices. It’s not glamorous, it’s not fun, but it’s necessary.
And while I was doing this, I had a realization: we don’t talk about money enough. It’s a taboo topic, avoided in polite conversation.
But if you’re thinking about quitting your job, money is the ONLY conversation that matters.
Because here’s the truth: Most businesses don’t fail because the idea was bad. They fail because the founder ran out of money before it took off.
If you’re serious about leaving your 9-5, you don’t just need a dream—you need a financial roadmap.
Let’s talk about everything you need to consider before making the leap.
Quote of the Week
“Risk comes from not knowing what you’re doing.”
Warren Buffett
The Hidden Costs of Leaving Your Job
Leaving your job isn’t just about giving up a paycheck. Here’s what else you might be leaving on the table:
💰 Salary & Bonuses: Walking away from an upcoming bonus, profit-sharing, or performance incentives? Check your payout schedule before resigning.
📈 Pension & Retirement Contributions: Your employer likely matches a percentage of your 401(k) or pension contributions. If you leave, you lose:
- Free money (their matched contributions).
- The simplicity of payroll deductions—now you have to manage it yourself.
- The option to merge your corporate pension into a private plan.
🏥 Health Insurance: If your employer covers part of your health insurance, expect higher premiums and out-of-pocket costs when you go solo. Before quitting, ask yourself:
- Do you have pre-existing conditions that might be excluded from private plans?
- Have you explored alternatives like ACA plans or spouse coverage?
- Can you afford COBRA if you need temporary coverage?
- Many people stay in corporate jobs just for the health insurance. I once had a client go back to corporate because his wife was diagnosed with cancer, and they needed the coverage.
🦺 Critical Illness & Disability Insurance: Many employers provide long-term disability insurance—which means if you can’t work, you still get paid.
- As a business owner, you’ll need to buy your own policy—and it’s expensive.
- Without it, an illness or accident could wipe you out financially.
🛑 Paid Time Off, Sick Leave, and Maternity Leave: When you work for yourself, no work = no income.
- Have you built a financial cushion for vacations, sick days, or parental leave?
- If you need time off unexpectedly, can your business sustain itself?
📊 Stock Options or Equity: If you have company shares, RSUs, or stock options, check your vesting schedule before leaving.
- If you quit too soon, you might lose unvested stock.
- Are you leaving before a major liquidity event (IPO, acquisition, bonus payout)?
🧾 Expense Reimbursements: Your company likely covers software, travel, conferences, even your gym membership. You’ll need to start paying for these yourself.
📚 Professional Registrations & Licenses: If your job covers industry certifications or regulatory fees, factor in that cost—some registrations are mandatory if you want to offer consulting services in the same field.
🚘 Car Allowances: If your company pays for your car in some way, expect to leave this behind and arrange alternatives.
Not planning for these can put unnecessary financial strain on your business and personal life.
How to Calculate Your Financial Runway
Your financial runway is how long you can afford to run your business before needing income. The longer your runway, the lower your risk.
Here’s how to calculate it:
- List Your Essential Monthly Expenses – Rent/mortgage, utilities, groceries, debt payments, insurance, etc.
- Add Business Startup Costs – Website, software, marketing, legal fees, coaching, etc.
- Factor in Taxes – Self-employment tax is higher than payroll deductions. Expect to pay 25-30% of income in taxes.
- Multiply by 6-12 Months – This is your buffer period—how long you can sustain yourself while building revenue.
- Plan for Unexpected Expenses – Car repairs, medical bills, family emergencies. Life happens.
Your runway shouldn’t just cover expenses—it should also give you peace of mind. The more stressed you are about money, the harder it is to build a business.
Your Income Transition Plan: From Side Hustle to Full-Time Business
Your business should generate consistent revenue before you quit. Here’s how to transition:
- Start With a Side Hustle – Use your free time to validate your business model while still getting a paycheck.
- Replace at Least 50% of Your Salary First – A safety net. If you can consistently replace half, you have proof of concept.
- Build Recurring Revenue Streams – Focus on offers that bring predictable income (retainers, subscriptions, repeat clients).
- Cut Expenses & Increase Savings – Reduce spending now so you don’t need as much runway later.
- Create an Emergency Fund – A 6-12 month buffer ensures you can focus on growth instead of panicking about paying bills.
The Unexpected Costs of Running a Business
Starting a business isn’t free. Here are some hidden costs most new entrepreneurs don’t think about:
💻 Software & Tools – Website, Phone, broadband, email marketing, design, scheduling, invoicing, payment systems.
📢 Marketing & Ads – Social media is free, but scaling often requires paid promotions.
📝 Legal & Accounting Fees– LLC formation, contracts, bookkeeping, tax filing.
🏥 Self-Employed Health Insurance – Often way more expensive than employer-provided plans.
📊 Sales Tax & Business Licenses – Depending on your location, you may have state or local business taxes.
👩💻 Hiring Help – Virtual assistants, freelancers, or team members to help you scale. 🪙 Professional Insurances – Depending on your field, liability insurance can cost thousands. 🏢 Office Space – If working from home isn’t feasible, expect to pay for co-working or office space.
Unexpected expenses can eat into profits fast—plan for them upfront.
Your 9-5 Should Fund Your Exit, Not Hold You Back
Quitting without a plan isn’t freedom—it’s financial stress.
Instead, use your corporate salary strategically:
- Invest in skills & coaching – Learn how to run a business while still getting a paycheck.
- Pay off debt – The less debt you have, the lower your monthly expenses.
- Stack your savings – The more financial security you have, the bigger the risks you can take.
Your job isn’t holding you back—it’s funding your future. Are you using it wisely?
See you next Wednesday.
