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Why I Took a Full-Time Job After 10+ Years of Freelancing

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On November 29th, 2021, after more than a decade of freelancing, I started a full-time job as a Senior Product Designer II at Instacart.

I realize this may be quite surprising and intriguing to my 60k+ annual readers who regularly look to my blog and newsletter for freelancing advice. Many of you are probably thinking:

  • I didn’t see that coming!
  • What changed?
  • Why now?
  • Why Instacart?
  • What about your company and your clients?
  • What about your blog?
  • Will you ever freelance again?
  • Isn’t this a step backward?

As I always have in the past, I’m excited to share the details of how I came to this decision and offer a unique perspective on what I think is a rare career pivot.

History & Context

First a quick recap. As many of you know, I started freelancing part-time in 2009 and graduated from college in 2012. With a degree in web and mobile UI/UX design, I got a job at a small web design agency. I worked there for 3 years and continued freelancing on nights and weekends.

In 2015, I left that job and began freelancing full-time. That’s also when I started my blog and newsletter. In 2018, I established my own company, Matthew’s Design Co. and have since completed several high-value, multi-year projects, worked with world-class brands, and won multiple international design awards.

By all accounts, my business has been thriving.

Contracting with Instacart

In June 2021, I was offered an exciting contract opportunity to work remotely with Instacart as a product designer. I decided to maximize the opportunity and agreed to a 40 hr/week contract that could be renewed every 3 months.

Why not, right? There was no risk.

I had the availability, it wasn’t a long-term commitment, and they paid my full rate. The projects were exciting and I got to add another world-class brand to my portfolio and resume.

I was immediately impressed with everything about Instacart. The projects, team, culture, quality, business approach, and management style were all the best I had ever experienced. I felt welcomed, supported, encouraged, and valued from day one. Everything was organized, communication was clear, and I appreciated how they respected everyone’s time, particularly in meetings.

It was the perfect fit for me. These were my people.

During my contract, I was asked several times about joining Instacart full-time. I wasn’t receptive to the idea at first (notably because I have my own successful business), but as I learned more about Instacart and what a full-time opportunity could look like, I started to consider the offer more seriously.

After 6 months of contracting, I did a round of interviews, received a formal offer, and decided to accept a new and exciting position!

Deciding on Full-Time Employment

Needless to say, deciding to join Instacart as a full-time employee was a massive decision and a huge shift away from running my own business:

  • Will I be happy with the compensation?
  • What will take my career further, Instacart or Matthew’s Design Co?
  • Will I be happy with the team and projects?
  • Am I ready to give up being my own boss?
  • What about my clients?
  • What about my company?
  • How will this impact my finances + taxes?
  • How will this affect my lifestyle?

When I stepped back to look at my career goals, I remembered that freelancing was never the end goal for me. I didn’t start freelancing because I hated my full-time job or wanted more freedom. It was a decision I made because it made sense, it was exciting, and I was really good at it.

The same was true when I started my own company, Matthew’s Design Co. It was the next logical step, not a lifelong career goal. I’ve always focused on continuous improvement instead of reaching goals and milestones. If my goal was to be a business owner, I wouldn’t have taken a full-time job at Instacart.

I also realized that I had maximized the potential of my own company. There’s a limit to how much work I can handle on my own each year and I reached an income ceiling. If I wanted to earn more from my business, I’d have to scale it up in a way I wasn’t comfortable with.

I don’t want to hire a project manager, employees, or subcontractors. Managing people doesn’t interest me. I love designing and building high-end digital products that make people’s lives better. My company was only meant to be a branded freelance business, not a firm or an agency.

Lastly, running a business is a huge amount of work. When I’m not actually working, I’m thinking about work. While I’m proud of my success, it’s come at a cost. The business is always at risk of failure if I’m not constantly maintaining it.

I had to be honest with myself about this in order to make the right decision!

Now that I’ve covered the background and rationale, I want to some additional thoughts in Q/A format.


Will I be happy with the compensation compared to my own business?

Compensation was one of the bigger factors in my decision. My starting salary was comparable to what I earned in each of the previous 3 years as a freelancer. In addition to that, there was a substantial equity component to my offer. I was also able to negotiate a signing bonus. Moving forward, I’ll be earning significantly more with less stress, less cognitive effort, and lower risk than if I stayed a full-time freelancer or small business owner.

Are the benefits good?

Benefits are another major aspect of the compensation package. As a freelancer, I was paying incredibly high costs for health and dental insurance. Having subsidized healthcare, dental, and vision insurance through Instacart will provide a massive annual savings. A matching 401k retirement plan along with many other perks make this an outstanding opportunity.

Are you worried about giving up the freedoms of freelancing?

No. The biggest freedom is working from home, which I’ll still have. I also get unlimited paid time off and reasonably flexible working hours. While there are some tight deadlines, no one is leaning over my shoulder every day. Instacart is extremely respectful of my time, they handle meetings efficiently, communicate clearly, and trust me to get my work done. When you combine that with not having to negotiate with clients, write proposals, manage projects, and collect payments, I think it’s a net gain.

Will I be happy with the team and projects?

Thankfully, I had the opportunity to work 40 hours a week at Instacart for 6 months before taking a full-time job. I’m staying on the same team and working on the same projects, both of which I love. There’s such a wide variety of teams and projects at Instacart that it’ll be happy and fulfilled for many years to come!

Am I ready to give up being my own boss?

Yes, for now. Being my own boss was never a lifelong goal and while I do enjoy it, it’s also incredibly stressful and time-consuming. In this season, I’m looking forward to relaxing and working on fun projects that I don’t have to manage myself.

What about my clients?

Right now I only have 3 long-term clients, all of whom have successfully launched their products. My plan is to stay involved with them for their “Phase II & III” initiatives throughout 2022 in the mornings and evenings (hopefully not weekends). I don’t plan on taking on any new clients in 2022.

What about my company, Matthew’s Design Co?

Right now, nothing is changing. My business and website will stay the same. I’m just not taking on any new clients in 2022, but I do plan on maintaining the 2-3 best client relationships I have and continue to work with them as needed, hopefully until their new startups outgrow me!

What about my blog, newsletter, and community?

My blog and newsletter aren’t going anywhere. While I haven’t had much time to focus on them through this transition, I don’t plan on retiring either of them right now. My blog and website attract tens of thousands of readers each year and as long as they are helping people, I’ll keep them active and continue to improve them.

The Freelance Institute will also remain active for now. I may even hire a community manager to foster more engagement. I’ve been torn on how to make the community even better, but don’t have any plans to retire it.

How will this impact my finances + taxes?

Financially, this is a major improvement. From a tax perspective, things will get a little tricky since I’ll have my business and W-2 income, but that’s nothing my accountants and tax advisors can’t help me navigate!

How will this affect my lifestyle?

Lifestyle is something I think most freelancers undervalue. When I started freelancing, I was single and living in an apartment. Now, I’m married with a house, land, a dog, and cat. My wife and I are thinking about moving to a new state and starting a family.

Circumstances change. In this next season of my life, if there’s an opportunity to have more stability, more income, more downtime, more growth, less stress, less effort, and less uncertainty, that’s an opportunity I want to pursue.

Final Thoughts

Not long ago, full-time employment meant commuting to work, navigating office culture, and climbing corporate ladders. But there was a major shift in 2020. Working from home became much more common. High-paying, fully remote job opportunities offer much of the same freedoms freelancers desire.

Career paths don’t have to be linear. It’s ok not to stay a freelancer forever once you start down that path. Going back to a full-time job doesn’t mean you’ve failed.

Freelancing was never the end goal for me, but I may decide to change directions again in the future — and that’s ok.

This is an excellent opportunity and I believe it’s the right decision for the next season of my personal life and professional career.

I’m extremely excited to be joining Instacart and plan to be there for years to come!

Last updated on September 7th, 2023

About Matt Olpinski
I've been freelancing since 2009 and have worked with over 100+ clients including some of the biggest brands in the world. I later started my own company Matthew’s Design Co. and now teaches 50,000+ freelancers each year how to succeed through his personal blog, newsletter, and community for freelancers.