Navigating the Uncertainties of Remote Work: Is a Second Remote Job Your Safety Net?

What if I told you I haven’t worried about losing my job in over five years? Not because I’m irreplaceable, but because I have something most people don’t – a backup plan that actually pays me.

I want to talk about something that might sound crazy – having two remote jobs at the same time. Now before you think I’m being unfair to my employers or I’m simply insane, hear me out. I’ve been doing this since 2020, and it’s completely changed how I think about job security.

My Remote Work Journey Started Before It Was Cool

I started working remotely back in 2015 – five years before the pandemic forced everyone else into it. Back then, remote work felt pretty risky, especially when you’re working for companies overseas. Those jobs can disappear overnight without any notice, and there’s not much you can do about it legally.

That’s when I decided to try something different. In 2020, I started keeping two remote jobs at once. And you know what? It’s been a complete game changer and frankly, I couldn’t go back to working just one job anymore. I’ve gotten used to receiving 2 paychecks monthly and not gonna lie, it feels good.

The Hard Truth About Remote Work Security

Based on experience I can say that remote work is amazing, but let’s be honest about the downsides that nobody wants to talk about.

The “Out of Sight, Out of Mind” Problem

When layoffs happen, guess who often gets cut first? Remote workers. There’s something psychological about not seeing someone every day that makes it easier for managers to put them on the chopping block.

Career Growth Gets Complicated

It’s genuinely harder to get promoted when your boss doesn’t see you daily. You miss those random conversations that turn into opportunities. You’re not there when decisions get made or when someone needs to think of who to recommend for a project.

Companies Are Still Figuring It Out

Many organizations are still experimenting with remote work models. Your position might get eliminated not because you’re doing bad work, but because they’re “restructuring” or trying to save money. Remote positions often feel more expendable to leadership.

Why Two Jobs Became My Ultimate Safety Net

So what can you do? Here’s my solution: have a backup plan that actually pays you while you’re using it.

Financial Security That Actually Works

The biggest win is obvious – money security. If one job disappears, I’m not scrambling to pay for my basic needs. I have time to find something good, not just accept the first offer that comes along.

Skill Development on Steroids

Working in different environments simultaneously has made me incredibly adaptable. I’m solving different types of problems, learning different systems, and staying sharp in ways that a single job never could provide. It’s like having two professional development programs running at once.

The Power to Say No

But wait, there’s more! Want to know the best part? The money security and the safety net of having a backup job give you the leverage that allows you to say no to lowball offers or projects that you don’t enjoy doing.

In my case, for instance, I don’t like doing customer service related jobs and when it’s part of the job description, I don’t go through with the job application. Same thing when someone presents a job opportunity with a low offer—without hesitation, I respectfully decline, inform the recruiter that I don’t accept offers below $xxx, and then I move on. And when I’m thinking about quitting one of my jobs, I don’t stress about it because I have the safety net of having another job.

The Sleep-Better-at-Night Factor

Not gonna lie, I sleep better at night because I rarely have to deal with financial stress and I’m not constantly worried about losing my job because I have options. That constant background anxiety about losing my income? Gone.

Before You Jump In: The Reality Check

Now for some reality check – working 2 remote jobs isn’t for everyone, and there are serious considerations you need to think through.

Check Your Contracts First

Some companies have exclusivity clauses or conflict-of-interest policies that prohibit additional employment. Getting fired for violating your contract defeats the entire purpose. Read the fine print before you do anything.

Can You Actually Handle Two Jobs?

Be brutally honest with yourself. If you’re already struggling to manage one job well, adding another isn’t the solution. You need to be able to deliver quality work to both employers, or you’ll end up with zero jobs instead of two.

Tax Complications Are Real

Your taxes become more complex, and you might jump into higher tax brackets. More money sounds great until you realize how much more you’ll owe in taxes. Plan accordingly and maybe talk to an accountant.

The Ethics Question

You need to be able to fulfill your obligations to both employers without cutting corners. Don’t take on more than you can handle, and be transparent where your contracts require it.

How I Make It Work: My System

If you’re thinking about trying this approach, here’s what’s worked for me over the past five years.

Time Zones Are Your Friend

Time blocking is everything, but I have a secret weapon – I work with US and UK companies which means I operate on different time zones. There’s only 1-2 hours overlap, which is totally doable. No mixing, no confusion, and both employers get my focused attention during their business hours.

Keep Everything Separate

Different computers when possible, definitely different email accounts, separate calendars, separate everything. This isn’t just about organization – it’s about maintaining professional boundaries and avoiding any potential conflicts.

Master Priority Management

I use apps like Trello or Todoist to track what needs to be done when for which job. Deadlines can’t slip through the cracks when you’re juggling multiple responsibilities. Find a system that works for you and stick to it religiously.

Don’t Forget to Take Care of Yourself

Two jobs can burn you out fast if you don’t actively manage your energy and time. I schedule breaks, maintain boundaries around my personal time, and say no to additional projects when I’m at capacity. Your health and sanity matter more than any job.

Is This Strategy Right for You?

This approach works best for people who already have strong organizational and time management skills, can find complementary (but non-competing) roles, handle pressure well, and value security over additional free time.

If you’re constantly overwhelmed by your current job, struggle with time management, or barely have time for your personal life, adding a second job will likely make things worse, not better.

Also, you need to value security over free time. Because let’s be honest – you’ll have less free time.

The Bottom Line

Remote work is still evolving, and we all need to find ways to protect ourselves. For me, having two jobs has been that protection. It’s not easy, but it’s given me peace of mind and financial security.

The key is being honest about your capabilities, careful about your choices, and strategic about how you implement this approach. It’s not a get-rich-quick scheme – it’s a calculated decision to trade some free time for significantly more financial and professional security.

What matters most is finding what works for your situation, your skills, and your goals. For some people, that might be building an emergency fund. For others, it might be developing a side business. For me, it happened to be maintaining two remote jobs.

The important thing is having a plan that helps you sleep better at night in an increasingly uncertain work world.

Have you ever considered working multiple remote jobs? What’s your strategy for dealing with remote work uncertainty? I’d love to hear about your approach – send me an email!