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Published November 8th 2021

How I Made a Successful Switch from Traditional to Freelance Work

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Working as a freelancer has become increasingly popular, particularly during the pandemic. Some freelancers took the opportunity to start a side hustle from home while still keeping their 9-5 jobs. Others have fully made the switch from traditional work, building freelance empires as their main source of income. 

Trust me, I’m one of those people. I can tell you there are numerous perks to freelance arrangements, including the flexibility to work remotely and the autonomy of being your own boss. But freelancing is not for everyone, and it can be a challenging career path. Working without a safety net and pouring all of your free time into building and protecting your brand can be daunting. 

I’ll provide you with some of the benefits and challenges of freelancing so you can decide if it’s right for you. Then, I’ll offer some of my best tips for would-be freelancers to make a smooth transition from their traditional jobs. 

Why should you consider freelancing?

While the COVID-19 pandemic certainly changed the world of work, shifts toward remote, hybrid, and freelance arrangements began before - the pandemic just hurried them along. But when it was mandatory, many individuals got a taste of WFH and now prefer to offer their skills in a more flexible capacity. 

Remote and freelance work can be very productive and lucrative for freelancers and those who employ them. In fact, freelancers contributed over $1.2 trillion to the US economy last year. In addition to flexibility of working hours, freelancing allows professionals greater control over what projects and clients they choose. It also allows them to develop organizational and project management skills and build professional portfolios that might not have otherwise been feasible. 

But as I found - working on your own can be a major drain on your energy if you’re not prepared. It can be difficult to get established in relevant industries, and not every freelancer will have the marketing know-how to go viral and gain a wide customer base. Plus, if you don’t have a financial safety net, the inconsistency of income might not appeal. 

I’m here to help you think critically about the potential switch to freelance work so you can get the pros while minimizing the cons. 

Is freelancing right for you?

There are many perks of building a freelance business, but it’s hard work, and it’s not for everyone. These tips will help you understand if (and what type) of freelancing is right for you:

Do some soul-searching

Before you take the plunge, ask yourself why you want to get into freelancing. If your answer is something like, “I’m annoyed with my boss,” then maybe you should not make the switch on a whim. There are ample ways to upskill and pivot between fields while maintaining a traditional work arrangement, so freelancing should not simply be used as an out of a job you don’t enjoy.

The best freelancers are self-motivated, organized, and able to thrive without structure. If these traits do not describe you, then perhaps freelance is not your calling right now. This is not to say you can't develop these qualities over time and consider freelancing later on. Or, consider keeping your current position and try freelancing on the side to see if it works for you. 

Assess your professional skills

Another question to ask yourself is what marketable skills you have to offer to clients. Some common fields freelancers work in are writing, editing, marketing, web development, software development, and graphic design. 

Some people wrongly assume freelancers are amateurs in their fields, but this is not always the case. While some use freelancing to build up their skills, many are already highly skilled in their fields, and lots are (or were) traditionally employed in those industries for years. If you have marketable skills to offer in fields where there is high demand, you might be able to make more money freelancing than you do in your current job.  

Assess your “soft” skills 

As part of your skills assessment, you also need to assess your so-called “soft” skills - that is, the things you can’t get a degree in, like resilience and emotional intelligence. When applying to jobs, it may sometimes feel like “hard” skills are prioritized in the vetting process. But if you’re planning to be your own boss, your main employee - you - had better have all the personal traits critical for success in a flexible work setting. 

I’ve said it before, and I’ll say it again - it is absolutely imperative that freelance professionals are organized, self-aware, intrinsically motivated, and practice good time management. While these are skills that can be developed, some personalities are naturally more inclined than others. If you want to succeed as a freelancer, you need to either already have these skills or develop them quickly before you start out. 

Use the right tools

Once you’re sure freelancing is the right path, you will want to equip yourself with some tools to help you. Things like time management, project management, and self promotion are all crucial for freelance success, and there are a few must-have tools for freelance professionals to do this effectively.

Look into freelance platforms

Unless you are already tapped into professional networks, you will probably need to do a lot of work early on in your freelance career to secure clients. As I found, platforms exist to help you make client connections. Some of the better-known freelance platforms include Upwork, Fiverr, and, but there are many choices of platforms that are credible. 

When choosing your platform, it’s important to think about what you want out of the arrangement. Some platforms, like Upwork, are better for long-term arrangements where you do a lot of smaller jobs for the same client over time. Others have higher barriers to entry, so they might not be the place to start if you are early in your career or just feeling out the freelancing market. 

Prioritize time management

This is the last time I’ll talk about time management - I promise. But it is probably the biggest sticking point for some freelancers. When you work from home, it can be easy to get distracted, forget to set boundaries, and work all hours. 

To avoid burnout, it’s absolutely imperative that you create an organizational system that works for you. This includes how you prioritize new projects, manage ongoing ones, automating manual tasks, and so on. 

It might be as simple as a Google Calendar, or you might want a full-on project management software suite as you advance. Particularly if you are a writer or marketer, there are also tools available to automate content research and creation, check your grammar and tone, etc. 

You may also need virtual communication tools to communicate with clients. Openness and clarity of communication are crucial to building trust when working remotely, and it will both make your life easier and make clients more likely to work with you again. The particulars are up to you, but using the right tools will go a long way in helping you thrive as a freelancer. 

Build your brand

Early on in your freelance career, I found it easy to rely on freelance platforms and word-of-mouth referrals to beef up my client base. But as I progressed, I started to think about my freelancing as a personal brand that I could cultivate online.

For one thing, as you build up your portfolio, you can feature it by creating a website. Then, you can harness social media to get your name out there and get traffic to that website. Consider free tools like Google Analytics to prioritize search engine optimization for your site and make sure you are ranking for the search queries relevant to your industry. 

You can also consider tools to partner with influencers so you can tap into existing social networks (in addition to building your own). This can be useful if marketing is not your area of expertise because you are partnering with industry experts whose whole business relies on loyal social media followings. 

Prepare for financial success

A final important step in my opinion towards freelance success is thinking about how you will manage money. Some freelance platforms have accounting features built in, but if not, you will need a reliable bookkeeping method. What’s more, freelancing is not always a steady stream of income, especially when you’re just starting out. That’s why it’s important to prepare for the worst even if you’re hoping for the best by having savings and a plan in case of financial emergency.

Once you get more established, you should also look into investment opportunities and planning for the future. While you might not have thought too hard about this in your traditional job, as a freelancer, you won’t have an employer offering insurance and a 401k. But you shouldn’t go without these things either, so be sure to look into options for self-employed individuals to protect yourself and your financial security. 


Freelancing can be an enjoyable and lucrative career move, but as I found, it’s also not without risks and challenges. Hopefully these tips will help you think critically about your switch to freelance work and make sure it is right for you. That way, you can know your area of expertise and build a successful brand that highlights your skills as a freelance professional. 

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