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Beyond the Nine to Five: Insights from Experienced Freelancers

May 28, 2024
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As an increasing number of marketing professionals opt to go freelance, we want to provide valuable insights for those considering freelancing or who may just be starting to freelance. We spoke to four experienced freelancers on the Wripple platform to find out why they do it, what’s been hard, and what’s been most rewarding about their journey.

Evelyn Creekmore

Content Director/ UX Content Strategist & Copywriter  

Years Freelancing: 7

Why did you go freelance?

I’ve freelanced on the side my whole career, and it’s a been a great way to gain experience and build new skills. My first full-time copywriting job was at a bank, and I worried about getting pigeon-holed as a financial writer. Through a professional organization for women in communications, I met freelance clients who helped me diversify my portfolio, which helped me get my first agency job.

I loved freelancing and often thought about doing it full time but couldn’t bring myself to leave the security of a full-time job. When the last company I worked for full time closed suddenly, I went into a job search frenzy that included freelance and full-time. I was taking all comers and extremely fortunate to get a six-month freelance contract with a dream client within a few weeks. I couldn’t have asked for a gentler introduction to the world of full-time freelance.    

What has been the biggest challenge you’ve faced as a freelancer and how did you overcome it?

The biggest challenge I’ve faced—and still face—as a freelancer is the peaks and valleys of work. I love the peaks and hate the valleys. I try to deal with them by staying positive and connecting with fellow freelancers for mutual pep talks. In the lowest valleys, my thoughts drift to the “security” of going full-time again.

What has been the most rewarding thing about freelancing?

The most rewarding thing about freelancing for me is the variety. Working on a variety of products and services across industries has always been important to me, and it’s been a big consideration in any full-time job search. I’ve been fortunate to have full-time jobs where something new and interesting was always happening, and with freelancing, the variety is amplified. I’m always learning something new.

 

Eli Grant

Digital and Marketing Strategist  

Years Freelancing: 7

Why did you go freelance?

I started freelancing as a way to better control my schedule. My wife and I had just had our second child and my previous agency role required a lot more travel and longer days and weeks than I was able to (and wanted to) devote to work.

What has been the biggest challenge you’ve faced as a freelancer and how did you overcome it?

I think I’ve had three big challenges.  

  1. Finding enough work to make freelancing financially viable. Wripple has proven to be an invaluable partner in this, allowing me to worry less about having to hunt down new business and instead focus on delivering great work.
  1. Deciding what kind of work and roles I want. As a freelancer, it has been tempting to take any role or project that is offered rather than focusing on things that are interesting, rewarding, and continue to help me build valuable skills and experiences. Over the past four years, I've been able to hone in on the types of projects I enjoy— and am good at— and focus more on these opportunities.  
  1. Having the confidence to be able to work on my own. Previously being part of large teams, I had lots of other talented people to lean on, but working on my own, I've had to build up my confidence in my knowledge and skills to be able to deliver without additional support.

What has been the most rewarding thing about freelancing?

The most rewarding thing has been gaining the additional family time and flexibility I hoped I would by going freelance. Being able to spend less time on the road and at the office and more time with my children has been the main accomplishment.

Christopher Santoro

Brand Strategist & Designer

Years Freelancing: 12

Why did you go freelance?

When I graduated from Massachusetts College of Art & Design back in 2012, it was a few years after the 2008 economic crisis. Full-time opportunities were either scarce or not good listings—job postings that wanted senior-level expertise for junior-level pay. Admittedly, my portfolio at the time didn’t have a lot of the UX/UI work that was sought after, so I started contract-freelancing from the get-go while bringing in private clients for my design studio.  

What has been the biggest challenge you’ve faced as a freelancer and how did you overcome it?

As a freelancer, you have to keep a keen eye on all the details—macro and micro respectively. You’ll have to be comfortable with wearing numerous hats, including the ones you’re not as savvy with, while ensuring high-quality work. You’ll have to be flexible and adapt to changes that occur within the project.  

The hardest challenge of all is learning how to do those things while protecting your energy and bandwidth. A big part of that is knowing yourself. Be honest (and kind!) with yourself, as well as the client, on the things you’re comfortable taking on. Don’t work longer hours than necessary. Not only do you protect yourself, but you end up protecting the client, the team, and ultimately the project scope.  

What has been the most rewarding thing about freelancing?

Being my own boss. It allows me to do my best work on my terms; from the type of projects I take on, to the processes I undergo for them. I’ve also found it gives me more of an opportunity to connect more deeply with my clients and help them work through problems and questions they may have. Most of all, as someone who’s always prioritized learning within my professional journey, it allows me to take on challenges and learn new skills without any of the pressures of a full-time position.

Nicole Victor

Dynamic Marketing Leader

Years Freelancing: 8

Why did you go freelance?

In 2016, I was actively engaged in the elections. After November, I felt the need to do more to help elect Democrats to office and to support causes I care about. I left the full-time work force and joined the freelance world, determined to continue to do paid work while doing more non-profit and volunteer efforts.

For the past few years, I've fulfilled my wish of doing good while also supporting myself. I’ve had some incredible contract roles with incredible people and amazing companies to challenge my mind. And I’ve been able to help non-profit organizations develop and grow to satisfy my soul.  

What has been the most rewarding thing about freelancing?

After leaving the agency world, I missed the ability to work across segments, consumers, and industries. Freelancing has allowed me to continue to constantly develop and learn from a wide variety of project types. I find that I thrive in this ever-shifting terrain, as it forces me to be agile enough to pivot strategies at a moment's notice. A positive side effect from freelancing is that I can devote more time and effort to developing my capabilities and honing my marketing skills.

Want to learn more about what it’s like to freelance in marketing today? Check out Wripple’s 2024 Team Up Report that digs deep into the perspectives of freelancers and the clients that hire them. You’ll gain valuable insights into the benefits and challenges of being your own boss, and how to put your best foot forward.

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To learn more about any or all of these solutions, contact your Wripple Client Lead, or request a demo.

As an increasing number of marketing professionals opt to go freelance, we want to provide valuable insights for those considering freelancing or who may just be starting to freelance. We spoke to four experienced freelancers on the Wripple platform to find out why they do it, what’s been hard, and what’s been most rewarding about their journey.

Evelyn Creekmore

Content Director/ UX Content Strategist & Copywriter  

Years Freelancing: 7

Why did you go freelance?

I’ve freelanced on the side my whole career, and it’s a been a great way to gain experience and build new skills. My first full-time copywriting job was at a bank, and I worried about getting pigeon-holed as a financial writer. Through a professional organization for women in communications, I met freelance clients who helped me diversify my portfolio, which helped me get my first agency job.

I loved freelancing and often thought about doing it full time but couldn’t bring myself to leave the security of a full-time job. When the last company I worked for full time closed suddenly, I went into a job search frenzy that included freelance and full-time. I was taking all comers and extremely fortunate to get a six-month freelance contract with a dream client within a few weeks. I couldn’t have asked for a gentler introduction to the world of full-time freelance.    

What has been the biggest challenge you’ve faced as a freelancer and how did you overcome it?

The biggest challenge I’ve faced—and still face—as a freelancer is the peaks and valleys of work. I love the peaks and hate the valleys. I try to deal with them by staying positive and connecting with fellow freelancers for mutual pep talks. In the lowest valleys, my thoughts drift to the “security” of going full-time again.

What has been the most rewarding thing about freelancing?

The most rewarding thing about freelancing for me is the variety. Working on a variety of products and services across industries has always been important to me, and it’s been a big consideration in any full-time job search. I’ve been fortunate to have full-time jobs where something new and interesting was always happening, and with freelancing, the variety is amplified. I’m always learning something new.

 

Eli Grant

Digital and Marketing Strategist  

Years Freelancing: 7

Why did you go freelance?

I started freelancing as a way to better control my schedule. My wife and I had just had our second child and my previous agency role required a lot more travel and longer days and weeks than I was able to (and wanted to) devote to work.

What has been the biggest challenge you’ve faced as a freelancer and how did you overcome it?

I think I’ve had three big challenges.  

  1. Finding enough work to make freelancing financially viable. Wripple has proven to be an invaluable partner in this, allowing me to worry less about having to hunt down new business and instead focus on delivering great work.
  1. Deciding what kind of work and roles I want. As a freelancer, it has been tempting to take any role or project that is offered rather than focusing on things that are interesting, rewarding, and continue to help me build valuable skills and experiences. Over the past four years, I've been able to hone in on the types of projects I enjoy— and am good at— and focus more on these opportunities.  
  1. Having the confidence to be able to work on my own. Previously being part of large teams, I had lots of other talented people to lean on, but working on my own, I've had to build up my confidence in my knowledge and skills to be able to deliver without additional support.

What has been the most rewarding thing about freelancing?

The most rewarding thing has been gaining the additional family time and flexibility I hoped I would by going freelance. Being able to spend less time on the road and at the office and more time with my children has been the main accomplishment.

Christopher Santoro

Brand Strategist & Designer

Years Freelancing: 12

Why did you go freelance?

When I graduated from Massachusetts College of Art & Design back in 2012, it was a few years after the 2008 economic crisis. Full-time opportunities were either scarce or not good listings—job postings that wanted senior-level expertise for junior-level pay. Admittedly, my portfolio at the time didn’t have a lot of the UX/UI work that was sought after, so I started contract-freelancing from the get-go while bringing in private clients for my design studio.  

What has been the biggest challenge you’ve faced as a freelancer and how did you overcome it?

As a freelancer, you have to keep a keen eye on all the details—macro and micro respectively. You’ll have to be comfortable with wearing numerous hats, including the ones you’re not as savvy with, while ensuring high-quality work. You’ll have to be flexible and adapt to changes that occur within the project.  

The hardest challenge of all is learning how to do those things while protecting your energy and bandwidth. A big part of that is knowing yourself. Be honest (and kind!) with yourself, as well as the client, on the things you’re comfortable taking on. Don’t work longer hours than necessary. Not only do you protect yourself, but you end up protecting the client, the team, and ultimately the project scope.  

What has been the most rewarding thing about freelancing?

Being my own boss. It allows me to do my best work on my terms; from the type of projects I take on, to the processes I undergo for them. I’ve also found it gives me more of an opportunity to connect more deeply with my clients and help them work through problems and questions they may have. Most of all, as someone who’s always prioritized learning within my professional journey, it allows me to take on challenges and learn new skills without any of the pressures of a full-time position.

Nicole Victor

Dynamic Marketing Leader

Years Freelancing: 8

Why did you go freelance?

In 2016, I was actively engaged in the elections. After November, I felt the need to do more to help elect Democrats to office and to support causes I care about. I left the full-time work force and joined the freelance world, determined to continue to do paid work while doing more non-profit and volunteer efforts.

For the past few years, I've fulfilled my wish of doing good while also supporting myself. I’ve had some incredible contract roles with incredible people and amazing companies to challenge my mind. And I’ve been able to help non-profit organizations develop and grow to satisfy my soul.  

What has been the most rewarding thing about freelancing?

After leaving the agency world, I missed the ability to work across segments, consumers, and industries. Freelancing has allowed me to continue to constantly develop and learn from a wide variety of project types. I find that I thrive in this ever-shifting terrain, as it forces me to be agile enough to pivot strategies at a moment's notice. A positive side effect from freelancing is that I can devote more time and effort to developing my capabilities and honing my marketing skills.

Want to learn more about what it’s like to freelance in marketing today? Check out Wripple’s 2024 Team Up Report that digs deep into the perspectives of freelancers and the clients that hire them. You’ll gain valuable insights into the benefits and challenges of being your own boss, and how to put your best foot forward.

Companies

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Freelancers

If you are a freelancer, or exploring the potential of freelancing, please learn more about working with Wripple.

Freelancers

If you’re an experienced marketing freelancer interested in joining Wripple, apply today.

Companies

Let us help assess your current modern marketing workforce capability and plan for success.