Remote Career & Money

Remote Career & Money

ByEvan Parker

Remote work isn’t a fairy tale—sometimes it’s 3 AM Slack messages, taxes in four states, and explaining to your grandma for the tenth time that “no, I don’t just play on my laptop all day.” Still, the freedom is real. If you want to build a sustainable remote career, find solid contracts, and keep your money in check (without losing your mind), you need more than just WiFi and hope. Here’s my practical playbook—no hype, just the stuff I wish I’d known in year one.

Finding Contracts That Don’t Suck

You’re not alone if Upwork makes you want to scream. Instead of bidding wars and $10/hour gigs, let’s talk about finding real projects with real budgets.

Real talk: My first remote contract paid $40/hour. Within a year, I was negotiating $85/hour for similar work—just by changing where and how I looked.

Where to Look (and Where Not To)

  • Direct Outreach: LinkedIn + email are gold. Personalize your pitch. Example: “Saw your team is hiring React devs—can I help you hit your Q3 roadmap faster?”
  • Curated Platforms: Try Toptal, Gun.io, We Work Remotely, and Remote OK. Higher signal, less noise, but you’ll need a strong portfolio.
  • Referrals: Ask current and past clients for intros. I send a one-line check-in every quarter. 60% of my gigs in the last 2 years came from referrals.
  • Skip: Race-to-the-bottom job boards, unless you’re building a portfolio from scratch (even then, set a floor for your rates).

Checklist: Landing Your Next Remote Contract

Step What to Do Pro Tip
1. Audit Your Profiles Update LinkedIn, portfolio, and Github. Show fresh work and results. Use keywords that match your target roles.
2. Outreach Message 5-10 leads a week. Keep it personal and brief. Include a quick Loom video intro—stand out fast.
3. Vet Projects Ask about budget, timeline, async culture, and payment terms up front. “Can you share how you typically work with remote contractors?”
4. Negotiate Respond with your rate and why (see next section). Never accept the first offer unless it’s great.

Negotiating Rates: Scripts, Math, and Mind Tricks

Here’s the thing: most remote contracts are negotiable. Seriously. If you don’t ask, you’re leaving money on the table.

How to Calculate Your Rate (For Real)

  • Research market rates for your skill (try Glassdoor, Levels.fyi, Blind)
  • Add 25-40% for self-employment taxes, insurance, unpaid sick days, and admin time
  • Factor in your experience (specialists can charge more)

Example math: If a full-time engineer makes $120k/year in your area, that’s ~$60/hour. As a contractor, aim for $75-90/hour to cover overhead.

Negotiation Script (Steal This)

You: “Based on my experience and the project scope, my rate is $85/hour. This covers not just development but also proactive communication and flexible availability. Let me know if that works for your budget.”

Them: “That’s a bit high…”

You: “I completely understand. Given the complexity, I’d need to stay in this range to ensure quality and availability. If that’s a stretch, we could adjust scope or timeline. What’s your budget range?”

Don’t undercut yourself. If they can’t meet your rate, it’s often a red flag for future headaches.

Async Workflows That Actually Stick

Async work isn’t about sending emails at midnight—it’s about building systems so no one’s waiting on you (or waking you up). Here’s what’s worked for me across teams and time zones.

Key Practices

  • Use clear, written updates: Daily or weekly standups in Slack/Notion. No one likes guessing.
  • Shared docs: Centralize specs and decisions in Notion, Google Docs, or Confluence.
  • Default to over-communication: If in doubt, write it down.
  • Set boundaries: Block focus time. Use status messages—“Heads down, back at 2 PM.”
  • Automate workflows: Zapier, Make (ex-Integromat), or GitHub Actions for repetitive tasks.

Async Tool Stack Cheat Sheet

Need Tool Why?
Project Management ClickUp, Trello, Jira Clear task tracking, async updates
Docs & Knowledge Base Notion, Google Docs Everything searchable
Communication Slack, Twist, Loom Async chat + video
Automation Zapier, Make, GitHub Actions Save hours every month

Taxes & Insurance: The Basics by State

I am not a CPA. But here’s what I’ve learned as a remote contractor bouncing between states:

  • Check state rules for where you live and where your client is based. Sometimes you owe in both.
  • Self-employment tax adds ~15.3% on top of federal/state income tax. Don’t skip quarterly payments (use IRS Direct Pay).
  • Health insurance: Healthcare.gov works for most, but check if your state has its own exchange. For travel, look into SafetyWing or Nomad Insurance as backup.
  • Track every expense. Tools like Wave, QuickBooks, or FreshBooks save your sanity at tax time.
  • Get a pro for year one if you can swing it. Find one who actually understands remote work (many don’t).

Pro tip: Save 30% of every payment in a separate account. It’s not yours (yet).

Insurance Checklist

  • Health: Marketplace/ACA or private plan
  • Professional liability: Hiscox or Next Insurance
  • Travel: SafetyWing
  • Equipment: Add your laptop/gear to renters/home insurance

Weekly Admin Routine (15 Minutes, Promise)

Staying organized is a pain—unless you make it a habit. Here’s my real routine (alarm goes off every Friday at 3 PM):

  • Review open invoices (send nudges if needed)
  • Log expenses (scan receipts or forward emails to accounting app)
  • Update time tracking/project boards
  • Check upcoming deadlines
  • Send 1-2 check-in emails to past clients (plant seeds for future gigs)

Total time: 15-20 minutes, max. If it takes longer, trim steps or automate more.

Quick Tools List

Remote Reality: One Story

Last year, I landed a six-month contract from a cold LinkedIn message. The negotiation started at $60/hour; I held out for $80. The client agreed—then the project nearly doubled in scope halfway through. Because we’d set clear async processes and scoped work in Notion, it didn’t turn into chaos. I invoiced biweekly, tracked time in Toggl, and stashed 30% for taxes. Six months in, they extended the contract and referred me to two more clients.

Moral: Get your basics right, and the rest falls into place. Even when everything else is on fire (figuratively or not).

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