The Accidental Freelancer: My Journey from Exempt Status and Paid Vacation to Hourly and Remote Work

Dennis Shiao
6 min readOct 26, 2018

This wasn’t planned, but I’m enjoying the ride 🚴

For 20+ years, I’ve worked full-time jobs. Wake up, shower, put in an honest day’s work. Come home, relax a bit, then repeat the cycle the next day. As a creature of habit, I enjoyed the routine.

Earlier this year, I was laid off from my job 😮

I applied to jobs and went through the interviewing process. I made it to the final round with a few opportunities, but a different candidate was chosen.

In the meantime, I picked up a few consulting projects (e.g. 10–15 hours per week in total) to keep me busy. Still, my intention was to find a full-time role.

The Possibilities Emerge

As I continued to search, I listed my role as a “marketing consultant for hire” on LinkedIn and Twitter. As past colleagues and contacts discovered my new status, they began to reach out with ideas and opportunities for project work.

I decided to take on as many projects as I could, to model the workload of a full-time job. Since these were flexible arrangements, I could always wind them down if a full-time opportunity came along.

While I’m still open to full-time opportunities, I’m enjoying my status as the Accidental Freelancer.

Here’s what it’s been like.

Getting Paid: Full-Time vs. Hourly

In my full-time roles, pay was a constant. The paycheck would come twice a month, whether I worked, took vacation or was sick.

These days, I’m only paid when I log hours.

Currently, my client projects are structured as a series of tasks. I complete the tasks, while tracking my time. Working at an agreed-to hourly rate, I then invoice clients based on hours worked each month.

It’s pretty dynamic — there’s not a defined range, such as “20 hours every week,” it’s literally “pay as you go.” All of my projects are remote, so there’s no office to report to. It’s been a big shift in mindset.

In my new arrangement:

I’m only paid when I’m actively working

And that made me realize how much waste exists in full-time jobs. I might put in a 10 hour day in the office and feel good about that. But there was the 90 minute lunch, the 60 minutes of hallway/kitchen chatter and many other moments that I’m not at my desk working.

I wouldn’t be surprised to find 5 hours of actual work time during that 10 hour day. In my freelancer arrangement, I’m paid for just those 5 hours.

Lately, there are days when I clock in less than 8 hours of work, but it feels like I spent the entire day working. I’m telling you, the 6-hour day is the new 10-hour day 😎

Also, when I think of the statement, “I had a good week,” that means something different now. In full-time jobs, a good week was the completion of a project, especially one that was done well.

These days, good weeks are also measured by how many hours I booked.

Daily Schedule: Dictated by Me 💪

Aside from schedule meetings and deadlines, I dictate my schedule.

Now that I’m on the outside, I look at office jobs and find some of the conventions a bit silly. I wanted to arrive at my desk early in the morning and not leave the office until a certain time. If I was never at my desk, I know that colleagues would wonder where I was.

These sorts of considerations don’t exist in the freelance world. Get the job done for your client and they’re happy. Doesn’t matter if you worked on it at 12am, 12pm or anywhere in between, so long as it’s complete and meets expectations.

In my full-time roles, I’d think about two modes: work-mode and non-work-mode. If I was responding to emails at 10pm at home, I’d concede the need to shift into work-mode. As a freelancer, I’m shifting back and forth and not even thinking about it.

Grocery store at 11am? Sure, no problem.

Sometimes, I’m at the grocery store in the middle of the day and cooking dinner for the family at 3:30pm.

To make dinner in the past, I’d need to rush out at 5:30pm, grab some groceries, then start cooking at 6:15pm, while the hungry family waited.

Note: I share cooking duties with my wife — didn’t want you to think that I did all the cooking in the household.

These days, I find pockets of productive time between 9pm and 11pm, when the house is quiet and I’m in a good mindset. Weekend mornings between 8am and 10am are similar.

The Office: It’s Fluid

Where I do my work is completely fluid.

My go-to spots include an office in the atrium of my house, the San Mateo Public Library, Le Boulanger and assorted Starbucks and Peet’s stores.

I thought about paying for a co-working space, but find the “hopping around approach” to be just fine and less costly.

My main overhead expenses are the food that I eat when “in the office,” and the parking meters 😊

For meetings with video conferencing, I take those at home, where there’s a controlled sound and visual environment. I take some calls and meetings from my car, as it makes me feel efficient: I’m getting work done while in transit.

Selling and Marketing: Me!

Without compromising the quality of work on my current projects, I need to be thinking about landing the next one — or, at least putting myself out there to attract interest.

Over my 20+ year career, I’ve worked with hundreds (perhaps thousands) of people. Someone out there has a need I can fill. But they may not know I’m available. I’ve been at this freelance things for only a few months.

While I haven’t directly pitched myself to people, I try and make my status known (e.g. “marketing consultant for hire” on LinkedIn). I want people to think of me when they come across a new consulting or freelance opportunity where I’d be a good fit.

I’ve been more active on LinkedIn lately, so that I’m top of mind with my professional network.

Loving the Chromebook

After being laid off, the first thing I needed to do was buy a laptop.

I had a modest budget to start with, so I looked at Chromebooks. I found an Acer Chromebook 14 for a really nice price and bought it.

There are no local applications or local documents on a Chromebook. Everything is stored in Drive and applications are either a Chrome (browser) plugin or run from a web page.

I’m a full G Suite convert, constantly using Drive, Docs, Sheets and Slides (oh my!). This post was composed in Google Docs via the Chrome browser on my Chromebook.

I love that I can save G Suite documents as Word, Excel, PowerPoint and PDF, as those are formats my clients use and expect. One downside is that Google now knows more about me than ever 😜

Everything Is Subject to Change

With freelance work, a project can last for 6 months or it can end tomorrow. The scope can change mid-way through.

It feels about right in the gig economy, subscription-based world that we live in.

And that’s just it: I’m MaaS, “Marketer as a Service,” and my customers can cancel at any time. Even en MaaSse 😆

That’s why “marketing yourself” needs to be constant. Your existing roster of client projects provides an insurance policy. If one project is cancelled tomorrow, you have the rest to fall back on.

Fitness and Happiness

I’m as fit and as happy as ever.

The flexibility in my schedule means that I can dictate my exercise schedule. And I’ve been exercising a lot 🏋️‍♂️

In the past, I had to work around a day in the office. In the fall and winter, when nightfall comes much earlier, it was challenging to find the motivation to exercise after work.

Life can work in mysterious ways.

I was bummed to be laid off. But having lived the freelancing life over the past few months, I wonder if this was meant to be. That this path I’m taking is the best one for me.

My Fitbit is setting new records and I feel great. I exercise, I’m in good health and I’m happy. Aint life great? 🤙

Thank you

Thanks for reading this far! To learn about the B2B marketing agency I founded, visit the Attention Retention website.



Dennis Shiao

Founder of marketing agency Attention Retention. Subscribe to my “Content Corner” newsletter: