Working from home on the couch

How to Negotiate Working Remotely or a New Work Arrangement

COVID gave office workers a taste of the freedom those of us who work online have enjoyed for years.

It turned employees everywhere, connected to their offices only by the internet, into instant digital nomads. Remote working was no different from … working. The old saying “80 percent of success is showing up”? Okay Boomer. Almost overnight, jobs became more focused on output: the work we created and the people who created it.

That’s a nice thought, right?

If you were one of these people, you gained a lot of power from your time in office quarantine.

Office politics? Commute making you late? Dress not appropriate for that client meeting?

None of that mattered anymore.

What mattered was YOU, and your contribution to your company.

You might be thinking “So why do I have to go back?” If you had a taste of the freedom of remote work and liked how it felt, this post is for you.

Because you don’t have to go back.

Leveraging your job to design a new career

If you worked and drew a paycheck during the pandemic and are still employed, you have leverage. You not only proved you can successfully work remotely – you also proved your worth as an employee.

Think of it this way: if you kept your job during the worst global economic crisis since the Great Depression, you must be a rock star.

COVID was an inflection point for companies worldwide, who realized they didn’t need offices anymore. It can also be an awakening for you.

You don’t need to travel around the country in a van to be a digital nomad. Or quit your job.

You just need an internet connection, and a plan.

You might be thinking that this all sounds good but does it really apply to me?

Women have a talent for second-guessing themselves when it comes to career, I know I do. Instead of leading with confidence, we often lead with introspection and questioning. That’s the gift of the female brain – to view ourselves within a greater context – but in corporate America, it can be a curse.

For example, take me.

I led the digital team at a major global firm where I launched many new initiatives and managed the firm’s most important digital assets. My fingerprints were all over these efforts.

Yet when I reached a point where I wanted to move on, I was filled with self-doubt as I dreamed of starting my own business. Though I’d quit other jobs in the past, there was more at stake this time: our son, a solid income, and dreams of early retirement.

By accident, I learned about the secret power I had on the day I gave my notice.

Instead of being shown the door, I found myself negotiating my exit. I wanted to leave, but the firm said “Not so fast.” The chief marketing officer called to ask me if I’d consider staying on in some capacity.

That gave my confidence a big boost.

woman dancing on a cliff
photo credit Joeyy Lee

So I began negotiating my exit. It didn’t take long for me and my employer to figure out how to make each other happy: I would stay on as a consultant, hire and train my replacement, and keep my salary until I was ready to part ways.

That gave me the runway I needed to put plans in place for my next move. And it gave me a chance to catch my breath, which is exactly what I needed to do to be able to start my new venture.

The big lesson I learned from that experience is that you don’t have to leave your job in order to design a new career. You just have to be ready to negotiate.

Negotiate like a boss
Photo credit: Brooke Lark

If you aren’t in a position to negotiate working remotely – say you’re a teacher being called back to the classroom when school reopens – there is a world of options out there if you decide not to go back.

Anything you do nowadays can be done in some form online, including teaching (more on that below).

Preparing to make a move

Here is my advice for designing your new “work-life,” based on what I learned from quitting my job during COVID.

1. Negotiate.

Employment isn’t a one-way street. Everything is up for negotiation. You can negotiate a remote working arrangement or leaving your job the same way you negotiate terms when accepting a new position.

When thinking about your next move, try to see things from your employer’s point of view. Understanding your value will put you in a good position to start the conversation.

Think about what you’ve done at work. Have you launched a successful new program? Has your work been credited with expanding sales or getting new clients? Remember, there is a reason you are getting paid for what you do. Try to quantify the “what you do” part. It will help you understand your worth.

Go back and read your annual reviews. I bet you’ll find some confidence boosters in there.

Also think about what the company gains from you leaving. Okay, this is a little tricky, but it can be another source of empowerment.

If you have a high salary, the company stands to save money when you leave. They might even pay you a severance because in the long run, it’s a cost-saving move for you not to be on the payroll.

Your leaving also gives your company the chance to do things differently – to restructure the team or promote a high-performing employee into your job.

The clean slate you are waving in front of them doesn’t diminish your value. Instead, use it to your advantage.

When I was in the process of leaving my job, profits at the firm were down. I knew there were parts of my job that weren’t a priority in an economic downturn, like running ad campaigns. The part of my job that wasn’t optional, managing the website, could be handled by a smaller team.

Approaching the situation as a “win-win” is a great way to begin negotiating.

2. Write a proposal for your employer.

Turning in your two-week notice is one way to quit, but there are other ways to do it. Writing a plan before you begin the conversation helps you figure out how to design your new work arrangement.

Let’s say you don’t want to leave your job but discovered during COVID that you could do it in less time at home because you had fewer meetings and were able to work through lunch.

Your plan could propose moving to a part-time schedule so you can build more balance into your life. And the way that happens is by working remotely four days a week.

Include all the essential functions in your job and how they would be covered. Make your plan read like a pact with your employer.

Share your plan with a trusted confidant at work and ask for a critique. Remember that person won’t have the confidence you have built up around designing your new work-life, and out of concern for you may try to talk you out of it. Let them know you are looking for feedback on the plan – ways to tweak your pitch to make it more enticing. Who knows, you might even wind up inspiring them!

Schedule a meeting to negotiate your request and share the proposal at the meeting. This will serve as a de facto agenda for your meeting. For me, a plan also takes the edge off. Having something in writing is a way of legitimizing your request.

3. Write a plan for you.

Now for the fun part! You get to create your dream job life on paper.

Working from home with kids
Photo credit Ketut Subiyanto

Start with big goals. And yes, those can be life goals. If your dream job is working 30 hours a week and being able to pick up your kids from school, guess what? That is a work goal, too.

The pandemic taught us that there is no shame in mixing work and life goals together.

Quarantine made it okay to be an employee AND a human because there was no hiding one from the other during the pandemic.

Being interrupted in meeting by your kid who needs help setting up his Zoom class? Happened all the time. Holding a team meeting from the couch in your living room? It’s all good.

The pandemic dragged the big “secret” out in the open: When we go to our jobs, we don’t stop being humans. It’s OK to prioritize your personal goals when thinking about your job.

Once again, so it really sinks in: It’s OK to prioritize your personal goals when thinking about your job.

Need inspiration? Think about what you’ll be missing by staying in a job you don’t love.

Write an elevator pitch. This is a short introduction that helps explain yourself to people who don’t know you. It’s a great way to start your plan.

It’s sort of like a branding exercise, where you boil yourself down to several really awesome bullet points.

You can use this pitch as a guiding light to keep you focused. If you decide to leave your job, it will be helpful on the days when you feel adrift – and if you are embarking on a new adventure, there are bound to be some of those days 🙂

Next, think about your goals, your pitch, and then try to write down some actionable steps you can take toward reaching those goals.

Here’s my example:

Elevator pitch:
Alice Cervantes is a writer and digital marketer who specializes in creating content and the digital channels used to promote content. A former journalist, she blends story-telling with a deep knowledge of the digital space to create meaning and awareness for businesses.

Build a fulfilling career that allows me to use my creativity to inform and inspire and to make a difference in people’s lives while giving me the freedom to travel.


  • Create a personal brand
  • Buy domain & write tagline
  • Build website
  • Create legacy content
  • Launch website
  • Promote website and services

I’m currently working on that last bullet point, which reminds me I need to update my plan. What a good feeling that is … just having typed it out, I realize how far I’ve come. 🙂

4. Get a career coach.

When I first heard about career coaching, I thought it was the kind of job that wasn’t a real job.

Boy, was I ever wrong! Luckily, my former employer got me a career coach, because I can’t say that I would have hired one on my own. But I’m grateful to have had the experience of working with one.

Career coaching gave me the confidence I needed to make a change and then showed me how to do it.

Career coaches are kind of like therapists for work. They are professional sounding boards who let you share your struggles and ideas and feelings, but that’s not the whole of what they do. They are experts at helping you create a plan to achieve your goals, sort of like making your dreams actionable.

I will never forget being asked by my coach to design a plan to deal with a specific problem goal I had shared. I thought – this is crazy, and will never happen.

And then a month later, BOOM. Mission accomplished.

And that was just the starting point. From hitting work specific goals to figuring out how to design a new life, coaching was the vote of confidence I needed to think big and keep myself on track.

5. Form a support group.

When I shared my plans to leave my job on Facebook, my hive exploded with support. Many friends reached out to congratulate me, and a few of them were interested to know more. So I decided to continue the conversation and started a support group.

There were just three of us for the first meeting; the people who had reached out to me. Each person in our little group was contemplating making a change, a pivot of some sort.

We had monthly Zoom calls with no agenda, but we found a lot to talk about and learn from each other.

The group started to gel. We added a few members and leave our sessions brimming with ideas that sometimes spill into side sessions.

During the quarantine, these meetings also filled the need for social contact. But as life is getting back to normal, I am still finding them worthwhile. Who doesn’t love a meeting with girlfriends that requires no preparation? The best kind of meeting for sure. 🙂

Woman contemplating life looking down a road

Digital nomad tools

There have never been more opportunities to make a living virtually.

The digital space has expanded so much since I left journalism to work in it. Nowadays, you definitely don’t even have to be a “digital” person to make a living online. In fact, you don’t even have to have a website!

But I do want to cover websites because that’s what I’ve gotten the most questions about since launching my blog, and I’m a big believer in having your own real estate on the Internet if you can.

To build a website, you need these things:

  1. Domain – name of your website
  2. Hosting – server space where your website lives
  3. CMS – Content management system – a framework that allows you to easily build and update a website without code
  4. Content – the copy, photos and widgets for your pages

Domain & hosting

I bought my domain and hosting from Bluehost. Bluehost is one of the biggest providers of hosting out there, but the reason I went with them is customer support. You can actually call Bluehost and get a person on the phone! That person often can often fix your problem, too. Huge for someone like me, who’d rather be writing copy than writing code.

Plans start at $8 a month and come with a free domain.

Content management system

My blog is powered by WordPress, by far the top CMS and blogging platform. It is free and flexible, with seemingly infinite design and functionality options. You can create a blog, website or even an app with WordPress.

There is a learning curve with WordPress, but it’s worth investing in the know-how. And if you don’t want to build it yourself, there are thousands of people who will build it cheaply for you.

Fiverr. This is where to turn if you are looking for someone to build your website – or any digital marketing need.

Fiverr is a giant marketplace for low-cost, freelance digital services. From logo designs to voice-overs to website builds, if you have an idea for creating something digital but don’t know how to do it, you can find help here.

If you want to keep it super simple and don’t mind paying for a CMS, try Weebly, Squarespace or Wix.

These are solid “all in one” platforms that work well for those seeking a super easy website builder. The tradeoff is they are more limited in design and functionality. But that can be a positive, too, because you won’t drive yourself crazy with endless options and customization. These options will run you from $20 to $50 per month.

Building a career online without a website

I like having my own website so I can control all aspects of my content and am not subject to another site’s rules, which could affect my business. But if you’re willing to play on someone else’s turf, there are many other avenues for you to explore.

Whatever it is you do, there’s a good chance there is a business out there that will bottle it and sell it for you online.

The best example, of course, is social media. You cultivate a following and leverage your audience to earn money through advertising or business deals. But you don’t need to have thousands of followers to make money online.

Create an online course and teach your skills

Going back to my teacher example, let’s say you love to teach but don’t love standing in front of a class all day. Or maybe you’re a knitter who loves to talk about knitting but doesn’t want to open a store of your own.

Udemy is a great place to set up your virtual classroom or take classes yourself. Udemy’s motto is “teach the world online.” It offers courses to more than 40 million people in 65 languages.

Skillshare is another online course marketplace that offers access to 25,000 video courses for a flat fee. You can also upload your own classes to Skillshare and earn money each time someone views your video. You can click here to get 30 percent off membership.

Design your own line of merch

If you’re an artist looking for a way to monetize your art, you can upload your designs and sell them on hundreds of products without any upfront costs. Printify, Printful and Society6 are websites that offer print-on-demand manufacturing of custom T-shirts, flip flops, iPhone cases and home decor – even pet beds!

This post tells you how you can create your own line of merch for less than $20.

You can sell these items on your own website, or you can sell them on other channels like Etsy or EBay.

If you are still with me at this point, and have found yourself starting to think about your next move, I hope you will continue to explore your dreams and see where they take you.

Or you could always buy an old VW van and drive into the sunset 🙂

Vinage 60s VW bus
Photo credit Martin Kallur

Advertising Disclosure: recommendations in this article contain links that may pay me a small commission, at no cost to you, when clicked. As always, thank you for your support.

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