Fully Booked VA Blog

Starting Your Own Business: 6 Steps to Conquer Freelancer Self-Doubt

Fear. Self-doubt. Overwhelm.

What if I’m making a biiiiiig mistake?

The truth is, we’ve ALL been there. I don’t know one single person who jumped on the freelancing train with nary a worry. Not one single person who waltzed into this new lifestyle and career choice without SOME sort of negative nagging thoughts. But I do know some people who let the fear and overwhelm stop them in their tracks. They hold on tight to the “What if I’m making a big mistake?” refrain while they continue to go to jobs that make them miserable, day after day, week after week. What these people need is a plan to deal with overwhelm, which in turn will make them feel better prepared for the rollercoaster of freelance life.

And this is exactly what Caroline Peterson, this week’s guest blogger, is here to talk about.

Thanks for sharing your insights, Caroline!

So you’ve decided to start your own business or jump into the freelance world? Welcome to the controlled chaos club!

Early in the year, I left my corporate job as Senior Copywriter to pursue starting my own copywriting business. It wasn’t a decision I took lightly. I had been planning it for quite a while before I turned in my resignation.

Since then, I’ve found myself skateboarding around on the wildest learning curve I’ve ever had the pleasure of riding. Feel the fear and do it anyway is my constant motto as I find myself having to have to push through the self-doubt (and that nagging feeling of getting one more thing done on my never-ending to-do list). Since starting my business, there are quite a few other real-world tips that have helped me along the way.

And on the off chance that you, too, are struggling with a bad case of freelancer self-doubt, here are my recommendations.

1. Have a Plan Before Day One

Even if you’re doing freelance work on the side of your current day-job, it’s imperative to set up a schedule to accommodate finding clients and working on client projects. In my case, I found a couple freelance clients and did copywriting work with them before and after my job, as well as on the weekends.

Doing this gave me a good idea of what kind of work I could expect if I did this full time.

More importantly, I planned how much time we would need in order to save and have enough money for a cushion to start my own business.

That cushion has been helpful and sanity-saving while I get my freelance business off the ground. Sure you could up and walk out of your cushy paying corporate job, but for a Type-A planner like me, it was nice to have that savings while I adjusted to the irregular paycheck of freelance work.

2. Set up Goals as Reminders

There are guaranteed to be tough freelance days– heck, weeks– and on those days I like to pull out a little sheet that lists the reasons why I started my own business. It can be something as simple as, “Setting my own schedule” to give me the motivation I need to keep pushing on through the rough patches.

Additionally, you can set up monthly goals to keep you on the straight and narrow.

For me, the first few months of setting up my business meant doing a lot of back-end work, such as figuring out a bookkeeping software, setting up templates for contracts, and finding a project management software to use. (I love Asana by the way.) These may have been boring goals, but they were goals nonetheless.

You have to remember, a good portion of your hours, if not at least half, will be dedicated to doing the menial and tedious administrative work of running a business. And that’s okay!

I probably had these grand delusions that I would just be writing on the beach all the time, rather than sweating over how to invoice my next client and which software I should use for that.

Getting realistic with your goals is key to not burning out in overwhelm.

3. Create a Schedule that Works for You

In the beginning, I told everybody I would stick to what my normal corporate hours were: 9 to 6. I quickly realized that starting a new business, with few clients, meant I didn’t have a ton of work to do at first and would end up being chained to my desk all day unnecessarily.

It was pretty demoralizing!

Now, I set up my mornings specifically for prospecting new clients and answering emails for current or potential clients.

The rest of my day is then spent working on current projects for clients or updating my website, which I’m redesigning. During my afternoons, I also set aside specific days and times to batch edit photos, set my social media schedule, answer any website or social media comments and take online copywriting master classes.

Just having this regular schedule gives me a good idea of how much time I spend on certain tasks, and that helps me properly set up schedules for the following weeks, avoiding overwhelm.

Also, in the beginning it can be extremely frustrating when certain tasks take a long time to complete. I used to beat myself up for how long it would take to send one proposal to a client, but after I got that first proposal sent, I now use it for future templates.

Give yourself some credit and be forgiving. You are never going to perfect a new business right out of the gate.

4. Join a Freelance Network

Freelancing or starting your own business can be incredibly isolating, so it’s crucial that you find other like-minded business individuals. Facebook was my hero in this instance!

I joined a copywriting group, and it has not only been validating but also humorous to see how we deal with similarly irritating situations and funny client requests. Gina has an amazing community for freelancers within The #FullyBookedVA System where VAs and freelance writers can gather around a virtual watercooler.

It’s important to have some like-minded people to turn to when no one else around you can answer your questions. These “colleagues” are an invaluable resource, and the earlier in the process you cultivate it, the higher the rewards.

In real life, there are plenty of local organizations for small businesses or freelancers that you could join. Many often don’t even have a membership fee, but do once-a-month meetups at cafes to go over new things in your industry. It’s usually pretty informal and often they’re very welcoming to newcomers because–hey!– everyone was new once!

If there’s one thing to take away from this list, it would be to find your own network either online or locally so you know that 1) you aren’t alone and 2) you’re valid feeling overwhelmed, frustrated and–good God–just concerned whether or not this whole new business thing is going to work out!

Because, guess what? Everyone else feels that way at one point or another too!

5. Build a Support System

Nearly as important as getting your network in place, is leaning on your personal support system, whether that’s family, friends or old colleagues.

If you think about it, your personal support system truly knows you best, so when you’re looking for a little ego boost, it’s helpful to reach out to them. Even if it’s just for a simple pick-me-up or to remind you of that one time you did that funny thing–like wear a Spice Girls T-shirt in high school–you can always count on the people who know you to make you smile.

And that’s incredibly important during this roller coaster period.

I’ve found that when I’ve opened up about my struggles or pushing through the constant freelancer self-doubt, many of my friends or family confessed that they’ve encountered similar struggles in their careers.

I also meet up with old colleagues for lunch every once in awhile. It has been helpful staying in tune with what’s going on in the ad agency world, as well as keeping my Rolodex (Does anyone use those anymore?) updated so I know who I can reach out to if I need an Art Director or Photographer for a particular client project.

The key is to lean on the people you admire in your personal support system.

I’ve quite literally reached out and asked, “What do you think I’m good at?”

You’ll most likely be happily surprised to hear some of their answers and also intrigued at what other people think about you in terms of career possibilities.

6. Know It’s a Rollercoaster Ride

Starting something outside your comfort zone, whether that’s going freelance or starting your own business, is going to be filled with ups and downs.

I was confident when I started my business that it would be successful and while that’s still true today, there are times I’m upset it’s been a slower start than I anticipated.

The important thing is to buckle up, know it’s going to be a crazy-fun ride and keep going.

Once I land a client, they often keep me because they like working with me; the problem is finding more of those similar clients during the slower times.

This search can be the most demoralizing part.

That’s when it’s imperative to remain confident, pull out that list of reasons why you started a business or went freelance, and lean on your network and personal support system. It’s a tough thing to do – always having to pull yourself up by your bootstraps and remind yourself of why you’re doing this! But it’s important to be your own champion and surround yourself with people who will do the same.

Here’s to many more years of controlled chaos success!

Ready to kick off your freelancing journey? Join The #FullyBookedVA System and let’s do it – together! 

Caroline Peterson is the woman behind Not Your Average Gal, a lifestyle brand immersed in the world of travel and living an unconventional life. She recently left her ad agency job as Senior Copywriter to jump – feet first – into pushing through self-doubt by starting her own copywriting business. If you’d like to take her up on any of her word wizardry, c’mon down and get in touch

Gina Horkey

Gina Horkey


Gina Horkey is a married, millennial mama from Minnesota. Additionally, she’s the founder of Horkey HandBook and loves helping others find or become a kickass virtual assistant. Gina’s background includes making a living as a professional writer, an online business marketing consultant and a decade of experience in the financial services industry.

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