The Successful Freelancers Journey; Challenges, Recessions, And Lessons


Are you thinking of starting your own business? Or are you a freelancer looking to improve your skills and increase your rate? If so, this article is for you. 

In this article, I will cover an interview I did with a freelancer and a business owner. In this interview, they share their personal experiences throughout their freelance journey. These individuals and I by no means speak for all freelancers and business owners, but their experiences mirror my own, and valuable insights can be gained from their stories. I hope you find this information valuable!

The topics covered:

  • Perks of freelancing.
  • Biggest worries for freelancers and business owners.
  • Things freelancers and business owners wish they knew sooner.
  • Who is cut out to freelance? What does it take?
  • And working a 9-5 vs. working for yourself.

The individuals I interviewed are Rayna Opaku, who works as a freelance Copywriter, and Max Lord, who is the Owner and Creative Director at Bridged Media.  Rayna has successfully managed multiple clients freelancing and sustained a nomadic lifestyle through her freelancing endeavors. Max built his small videography passion into a thriving videography company that assists businesses throughout the UK and continues to expand. Take a look at what they have to say about their professional journey.

Q. 1: What factors (such as flexibility, control over schedule, etc.) do you like about working for yourself? 

No need to request time off or sick days from an employer. “If I need to take a day off, I just take a day off. It’s nice to be able to pick my schedule. 

I don’t need to ask anyone for time off. I don’t need to beg anyone to switch my shift… I can be like, ‘Hey, I am not available.’ Done. The amount of work-life balance is incredible… now the idea of asking someone, another human, for time off… is ridiculous.” – Rayna.

“The idea that you always have to work for someone for the rest of your life should die.” 

– Rayna

More financial independence and security, especially through a recession or inflation. “It gives a lot of financial stability and independence. Inflation has not affected (me); my rates just increase.” – Rayna.

Now, this is not to say freelancing is always smooth sailing. Many freelancers experience income volatility for the first 6-24 months. However, freelancers who consistently attract leads set competitive rates, and lead with confidence can cultivate a stable income. 

Recessions can be great news for freelancers! Since companies are cutting costs and reducing labor, private contractors and freelancers can land more projects.

Freedom to operate your business in a way that fits your lifestyle and values. “One of the best things about working for yourself… is you don’t have to run things exactly how other people do. Sometimes I will have a day off in the middle of the week and then substitute that day for working a little more on a Saturday. To some people, that’s nuts, but I enjoy that because I can get things going.

I don’t mind working massive hours on a Monday or a Tuesday with the benefit of having way more time off later in the week. Having that ability not to have to show up for work or show up hard for work is something I enjoy.” – Max.

Work-life balance is a challenge for most people, freelancers included. However, over time a freelancer can find a schedule and workflow that meets their needs! This opportunity isn’t usually available in a 9-5 position where your employer dictates your time. 

Q. 2: What were some of the biggest worries/stressors you had in the first 12 months of starting to work for yourself? 

Self-doubt and imposter syndrome. “I wasn’t sure if I could take on this client. I wasn’t sure I could write that article. I wasn’t sure my portfolio was good enough. I wish I had not done that (worried so much).”- Rayna

.“The biggest worry I had when starting was that I wasn’t at the level where people would take me seriously…. In video, you can make a blockbuster-looking video, or you can shoot something on your phone. When I was starting, I wanted to make really good content, but I didn’t have enough experience… to know what makes a good video.

Through doing it enough times and going through the process… and listening to clients… I’m at a point where I’m very comfortable having a conversation with a client knowing I can produce something really good for them.

But when I started off, I was really worried: ‘Are they going to see through me?’ ‘Are they going to see through the fact that I don’t have all that experience, that I don’t know what I am doing all the time?” It’s kind of like imposter syndrome. You may think, ‘Am I good enough yet? – Max.

Imposter syndrome is more common than we think. Time Magazine comments that as much as 70% of individuals experience imposter syndrome throughout their life!

Covering expenses and bills for the first 12 months. “The first 12 months were rocky, and that’s on me. Had I increased my rates and bid for higher jobs, I don’t think I would have struggled as much.” – Rayna.

Those who run a business or freelancers must become expert budgeters. There are a variety of tips and techniques to survive rough periods and ensure you have the time to pursue high-value projects. 

Q. 3: What are a few things you wish you had known sooner? 

Have the right mindset and scale faster. “How important your mindset is… it’s very true. As a freelancer, there is no one but yourself… I wish I had known if I had just told myself I could do something, I could do it. When you apply for a job, if you don’t feel a bit sick when you quote your price, then it’s not high enough. Because a lot of time I think it’s too high, but they would say ‘Ok. 

The biggest change that led to an increase in my salary was… when I decided, ‘you’re going to be better cause others are doing this who don’t have the skills you have.’ I tracked my income, and you see it shoot up… it was nice to see the direct results of your efforts and a mindset change.

Scale up faster and believe in yourself because there are a lot of people out there doing what you’re doing for a lot more money, and they’re maybe not even as good as you….”- Rayna

Building the right mindset and qualities to freelance ensures you endure rough patches, self-doubt, and other hurdles you will inevitably face. 

Raise your rates regularly. “Don’t be afraid to raise your rates. Don’t be afraid to apply even if you don’t have the experience… Don’t be the one to say no to yourself… let them tell you that you don’t qualify for that; you don’t know!… Don’t tell yourself you’re not qualified, don’t write yourself off.” – Rayna.

Avoid “shiny syndrome”; instead, focus on getting good at one thing. “Number one, which I am still working on, really prioritizes effort that is in line with the bigger goal your after. It’s easy to get caught up with ‘shiny syndrome’ in business, thinking, ‘oh, this thing’s going to help me do this or… that.’ If I make more social media stuff… or education or type of work, that will help me.

I wish I had known sooner; just focus on the simple thing you do well… focus on learning to make that one thing well… and sell it well. Start there. Get crystal clear on how to make and provide that one service… and become an expert at… how to communicate how that can help someone….”- Max.

People have more money than you think, and they will spend it on what they value. Second thing, people have more money than you think… you should continue up your charging/rates every time you get a new project. If the person is unhappy with the price or can’t do it, that’s fine. Be okay to say ‘no.’” – Max

“If you are okay to say no to someone, that just means the yes’ are even better.” 

– Max

Delegate quicker. One fallacy I had was, ‘I am the only one who knows how to make the videos I make.’ to a degree, I am right, but the client doesn’t know if I’ve made it or someone else as long as it’s good enough for the client to go ‘Wow! That’s great! That’s a great product or service.’

If you’re growing a business… learn your craft, and once you’ve got a good enough product, learn how to get others to help… which frees up your time. Time is THE most important thing you have. – Max.

Q. 4: Do you think anyone can work for themself? Why or why not? 

“Yes, anyone can, but not everyone does. To work for yourself takes a certain level of belief in yourself… and drive… and not to be rude, but I don’t think everyone has that. Some people are not taught to go out of their comfort zone. This can go back to privilege and upbringing. If you have people in your life who push you to do better…then I think you will find it easier to work for yourself. Also, it helps if you enjoy running everything on your own.

I like to have a lot of control over my life. I just wanted to work for myself and have control over my schedule. If you are someone who is not a self-starter… you can learn, but you may have more of a difficult time. – Rayna

“I don’t think I can answer this. I think this is quite a grey question. If you enjoy doing something that can bring value to someone else… then yes.

You can run your own business… because running or starting a business is more about taking a bet on yourself and having courage… than having the know-how to run a business.”

You can always learn how to run a business and sell. But it all starts when you enjoy doing something, and you know someone would pay for that thing… As long as they love something and are okay with doing scary things… If you are okay with learning and the unknown, then yes, you can start a business.”- Max.

Q. 5: Have you ever had a period where you thought you should give up/work for a company? If so, who or what got you through it?

No, absolutely not… I almost worked with a company, but I felt we wasted time. In a company, I feel they need to make up reasons as to why they are paying you so much, so they pull you into a bunch of meetings. That same amount of work can be outsourced. There are people I work for that I have never met in person… there’s no need. They send me the brief every week. I write and send it back.” – Rayna.

“I haven’t. I have thought about what it would be like to work for a company because… I would get a cycle where I would do a bunch of work. I would finish that work and get paid for it. But guess what, there’s no more work because I hadn’t marketed. I hadn’t spent any time working on the business; I had spent too much time working in the business.

Now, if I had to get more work, I have this inner confidence to think, ‘You know what, if it came to it, I would spend a week sending outbound videos to local businesses… I would market my butt off.’ 

My best clients have come from sending a message to them. ‘Hey, I love what you do. Have you considered using video?’ I know if I had to, I could make it work. I don’t want to work a 9-5 for someone else doing something, knowing I could do a better job than they can. Which sounds a bit cocky, but I believe it. When I look at other companies, it’s not always my flavor. I’d rather stick to something I do well.” – Max.

Closing

Freelancing is not a one size fits all. Running your own show takes A LOT of effort and investment. But if you are willing to take the leap and consistently learn and try new things, you may find it’s one of the best investments you can ever make.

If you decide you’re ready to make the change, congrats. If you have already started freelancing or running your own business, I encourage you to keep going. It can be confusing and overwhelming to get started. However, the freelancing community is now thriving, and the mentors and resources we have access to make the learning curve shorter. One of the BEST freelancing mentors I have come across is Jamie Brindle. His guidance and resources are helpful for those just getting started and experienced freelancers. Check out his Instagram.

Jay Clouse also has a great Freelancing School Bundle Course which I took when getting started. This course covered business, marketing, and selling for Freelancers. The resources he provides in those courses are practical, and I still use many of the documents and recommendations now.

Best Wishes,

Nicole Littlejohn

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