BUSINESS

In January of last year, I had a moment that probably occurs to most of us.

I was staring blankly at a spreadsheet I'd built for someone else, sitting in a meeting I didn't need to be in, nodding at things I didn't really agree with. And I thought: Wait. Is this it?

I wasn't burned out (yet). I wasn't miserable. But I was deeply, existentially… bored. Like I was watching someone else live my life through a webcam.

Truthfully, this had been the way things were for a good while, ever since getting started on the corporate ladder of getting good jobs, learning office politics and trickling yourself up into the 'big leagues.'

That afternoon, I scribbled a question in my notebook: What would it actually take to leave this job — without going broke or insane?

This is the article I wish I'd found back then.

Not a "Quit your job and hustle till 2am!" motivational speech. Not a sugar-coated dream of sipping cocktails on a beach while passive income rolls in. But a realistic, 10-month roadmap for how a regular, risk-averse, slightly-overthinking office worker can slowly but surely build an escape plan.

Let's get into it.

Step 1: Decide You're Actually Going to Do This (Month 1)

This sounds basic, but it's the keystone.

Most people stay stuck because they think they want to quit, but they don't actually commit to it. It stays abstract — something Future You might do once you magically stumble across "the idea" or win the productivity lottery.

This is not the time to get yourself stuck on teasing the idea, or entertaining the thought, but not pulling through. Month 1 is the time when you decide whether you are actually committing to this or not.

  • Do you want more freedom, or just a less annoying job?
  • Are you trying to escape a boss — or a version of yourself?

Write it down. Make it real. Then tell one person who won't laugh at you. These are going to be your two tethers that will keep you grounded when the real time to quit comes around.

If you are like me, you are going to need these tethers very much. Do go back to the note you wrote, do bring the subject up to that one person now and again. The key aspect to keep in mind during this month is that you need to keep yourself in touch with the idea.

Feel your fears, face judgement from the comfortable side of yourself when you think about these things. All of this is essential to making sure that your plan is not going to flop.

Step 2: Cut the Fat, Keep the Freedom (Month 2)

Leaving your job doesn't just mean replacing your salary. It means rethinking what you actually need.

Here's what you should be doing in Month 2:

  • Review 3 months of expenses and decide what corners you can cut in your budgeting efforts (turns out, $180/month on Uber Eats was not "essential")
  • Identify your true minimum viable lifestyle — MVL (spoiler: it's not as scary as you may think, and it may even act as a form of meditation on the things you truly value in life)
  • Create a "Freedom Number" — the monthly income you'd need to semi-retire or go part-time

This entire prepping will give you something that is profoundly necessary at this point: a clear target. Remember, you are not trying to build a six-figure empire. If you are like me, you may just want to cover your bases and buy back your time.

That's exactly what you should aim for.

Step 3: Learn a Monetizable Skill (Months 3–4)

Now comes the part where we leave corporate fluff behind and start building something useful.

For me, monetizable skills were always tied to writing and digital marketing, because that's what I was very good at. For you, it could be:

  • Notion or Airtable consulting
  • SEO, email marketing, or content creation
  • Tech support for small businesses
  • Voiceover work or video editing

The goal here isn't mastery. The goal is to learn just enough to help someone with a problem they'll gladly pay to solve. If you can do that once, you already have one foot out.

I recommend what I call the Google curriculum:

  1. Pick one skill you're curious about
  2. Google the 10 best tutorials and do all of them
  3. Build a tiny project that proves you know your stuff (both to yourself and one potential client)

At the end of Month 4, you should be able to point at something and say, "I made this."

Step 4: Start Selling, Quietly (Month 5)

This is the scariest part. It's also where everything starts to change.

Month 5 is about putting your skill into the world, imperfectly as it is.

That might mean:

  • Doing your first freelance job for a friend
  • Selling a $19 template on Gumroad
  • Offering a free audit or strategy session to a stranger on Reddit

The goal isn't to get rich. The goal is to get paid once. To prove that money can come from you instead of just your job. This is a very necessary step that not only helps you psychologically, but also operationally.

One job down means one experience you can learn from, an opportunity to improve one thing in your life before getting to the next one. This is the lifeblood of the escape plan.

When that happens, something clicks in your brain. And you'll never look at your paycheck the same way again.

Step 5: Build Systems, Not Just Effort (Months 6–7)

By now, you've got proof of concept. You can make money outside your job. But you're probably doing it in an unsustainable way — lots of hustle, little structure.

It's time to think like an operator, not just a freelancer. This entire thing you are doing needs to be optimized, both for the sake of your paycheck and your time. To get started, you may find a few questions useful.

Ask:

  • Can I turn this service into a product?
  • Can I automate outreach, delivery, or onboarding?
  • Can I use content (YouTube, Medium, email) to generate inbound leads?

You don't need a 17-step funnel. Just build one repeatable process that doesn't eat your entire week. Once you have a unit that can produce money, you can look further out to making multiple units, or just a few that work really, really well.

Step 6: Create a Runway + Buffer Fund (Month 8)

Let's be responsible, shall we?

Month 8 is where you consolidate the financial cushion that makes quitting realistic, not reckless. This is the time to take your savings, investments and other financial accounts and see what situation you have on your hands. Ideally, aim for:

  • 3–6 months of living expenses (bare-bones lifestyle)
  • A "leaving cushion" of at least $2,000–$5,000 for emergencies
  • Income from your side business covering at least 40–60% of your basic costs

This is where your stress starts to drop and your confidence starts to grow. Truthfully, you are already more than halfway there.

Step 7: Make the Plan Public (Month 9)

Tell your partner. Your best friend. Maybe even your manager (depending on your relationship). This is the time to activate that point of no return boost that is going to get you over the threshold.

There's something powerful about making your exit plan visible. It forces you to treat it seriously. It shifts the narrative from "someday" to "I'm doing this." Especially because we're already in Month 9, the reality of it all will help you feel what this new life you are building may look like.

Bonus: If you've been reliable, many managers will respect your honesty. Some might even support your transition. I've seen people negotiate part-time contracts or project-based consulting roles post-exit. Keep the door open.

Step 8: Pull the Cord (Month 10)

This is it. You've built the skills. You've earned money. You've tested your idea. You've saved the buffer. Now, you get to trade certainty for autonomy, an equation which you should already be familiar with by now.

It will feel both thrilling and terrifying. That's normal. But remember: you're not leaping into the void — you're stepping into something you've spent 10 months carefully building.

Write the resignation letter. Take a long walk. Breathe.

You just changed your life.

Final Thoughts: Your 9-to-5 Was Training

One of the biggest mindset shifts I had to make was this:

Your career wasn't a waste. It was training for what comes next.

All those emails? Negotiation practice. Those meetings? Lessons in human psychology. Those PowerPoints? Your new sales pages.

You're not starting over. You're leveraging what you've learned over many years to create a new lifestyle for yourself. There is little to no resource wasted in this process, not if you look at it close enough.

So if you're sitting in your office chair today, wondering if you've missed the boat, you haven't. You're right on time.

Build slowly. Think long-term. And trust that if you commit to 10 months of focused work, you can earn something more valuable than money:

Your time back.

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