What I Wish I Knew About Freelancing Before I Started: 18 Untold Truths About Life as a Freelancer


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What I Wish I Knew About Freelancing Before I Started: 18 Untold Truths About Life as a Freelancer

Table of Contents

What I Wish I Knew About Freelancing Before I Started: 18 Untold Truths About Life as a Freelancer

To help aspiring freelancers avoid common pitfalls and challenges, we asked 18 experienced professionals from various fields to share the one thing they wish they knew before starting their freelancing journey. From CEOs to founders and operations managers, these experts share valuable insights, ranging from expecting long working hours to setting boundaries for balance.

  • Expect Long Working Hours
  • Prioritize Contracts and Ignore Emotional Pleas
  • Define Project Scope Clearly
  • Stay Vigilant Against Scams
  • Set Boundaries for Work-Life Balance
  • Master Communication and Marketing
  • Embrace Multitasking and Learning
  • Remember the Power of Networking
  • Learn Essential Freelancing Skills
  • Manage Your Freelance Tax Obligations
  • Focus on One Specific Niche
  • Embody Continuous Learning
  • Practice the Art of Self-Promotion
  • Persevere for Freelancing Rewards
  • Value Your Time and Expertise
  • Educate Yourself in Financial Planning
  • Prepare a Backup Plan
  • Establish Expectations Upfront

Expect Long Working Hours

One thing I wish I knew about freelancing before starting was having to work long hours. The common misconception about doing freelance work is that you can pretty much work from anywhere and have your work completed quickly.

But the reality is, freelancing means putting in long hours to meet deadlines and produce quality work, sometimes working well past six or seven in the evening. This might require you to adjust your mindset when it comes to extra work and be ready to put in the effort to succeed as a freelancer.

Matthew RamirezMatthew Ramirez
CEO, Rephrase

Balance passion-driven work and flexibility

Promoted by Fiverr

Freelancing is the best way to balance passion-driven work and flexibility – giving people the opportunity to have full autonomy over their career and how they want to work on a day-to-day basis. Whether you’re working at home or on-the-go, freelancers can choose the projects they want to pursue, then craft their work experience around it. As a freelancer, you have the freedom to travel the world, spend time with your family, and manage your own schedule.

As we continue to navigate a volatile economy plagued by layoffs and firings, independent work is a great vehicle for financial security. By not being tied down by a singular employer, you can take on more projects, be your own boss, and further develop your own service offerings with new skills – such as AI. With businesses relying on freelancers more than ever before, freelancers today can expand their horizons and work on projects of all shapes and sizes.

shai-lee spiegleman fiverrShai-Lee Spigelman
General Manager, Fiverr Pro

Prioritize Contracts and Ignore Emotional Pleas

My biggest piece of advice is to do everything decently and in order: don’t take shortcuts. If you’re using a platform like Upwork or Fiverr, make sure you’ve hashed out the details and received the order or signed a contract BEFORE you start working. Don’t do work until the money is in escrow. If you’re not on one of those platforms, the same thing applies. Insist on at least partial payment upfront.

Similarly, don’t take pity on the sob stories. 99% of the time, they’re the biggest jerks to work with, because if they don’t think it’s worth paying you your asking price, they’re not going to value what you do, either.

Beverly GearrealdBeverly Gearreald
Product and Operations Lead, Transizion

Define Project Scope Clearly

One thing most freelancers get wrong is the importance of clearly defining the scope of work for each project. Having a clear understanding of what is expected, including deliverables, deadlines, and any additional requirements, is crucial for successful freelancing. It helps manage client expectations, avoid misunderstandings, and ensure that both parties are on the same page.

By clearly defining the scope upfront, freelancers can accurately estimate their time and effort, negotiate fair compensation, and deliver high-quality work. It also minimizes the risk of scope creep and enables better project management. The clarity in scope ultimately leads to smoother client relationships and more successful freelance engagements.

Josh AmishavJosh Amishav
Founder and CEO, Breachsense

Stay Vigilant Against Scams

It’s not exactly news that the internet is filled with scams and fraudulent activity. Before I started freelancing, I thought the major freelancing platforms had taken serious actions to keep sketchy activity off of their sites. I overestimated what they’ve done.

So many of the projects I apply for are not what they claim to be. I’ve yet to get burned by one of these scams, but I’ve had to be much more vigilant than I initially expected.

Temmo KinoshitaTemmo Kinoshita
Co-founder, Lindenwood Marketing

Set Boundaries for Work-Life Balance

The one thing I wish I knew before embarking on this journey as a personal trainer was the importance of setting boundaries.

When I started, I was eager to take on every client and opportunity, often at the expense of my personal time. I’d be answering client messages late into the night and working on weekends. But over time, it started to burn me out.

One day, a fellow trainer suggested setting specific “office hours.” That changed everything. I communicated these hours to my clients and stuck to them. This not only helped me maintain a healthier work-life balance but also showed my clients that I value my time.

So, to anyone starting freelancing, remember: boundaries are crucial. They help maintain your sanity and professionalism in this dynamic world of freelancing.

Evander NelsonEvander Nelson
NASM-certified Personal Trainer, evandernelson

Master Communication and Marketing

One thing I wish I had realized before jumping into freelancing is the vital importance of communication and marketing skills, irrespective of the type of service you’re offering. As a freelancer, you are essentially a one-person business, and a major part of that is selling your services. That means being able to effectively communicate your value proposition, engage with potential clients, and navigate negotiations.

I initially thought the quality of my work would speak for itself, but quickly learned that your ability to market yourself and communicate clearly can be the deciding factor in landing that gig. No matter how good you are at what you do, if you can’t communicate that effectively, opportunities might pass you by.

Juliet DreamhunterJuliet Dreamhunter
Founder, Juliety

Embrace Multitasking and Learning

As a freelancer, be prepared to handle various tasks beyond your core skillset. Clients will often ask you to juggle project management, marketing, accounting, and client communication, especially if they are new to hiring freelancers.

Although the more things you know, the more jobs you can apply to and be paid for. To prevent getting overwhelmed—prioritize tasks, consider outsourcing non-core tasks, seek support from freelancer communities, and improve time management.

Include continuous learning, upskilling, and investing in your professional development so you can be future-proofed. Embrace the opportunity to develop new skills and provide a well-rounded service to clients.

Tristan HarrisTristan Harris
Demand Generation Senior Marketing Manager, Thrive Agency

Remember the Power of Networking

The need to constantly market myself as a freelancer is stressful. Having a strong network is the backbone of generating new leads. There is so much to learn from other thought leaders in your industry, so don’t be afraid of fraternizing with your competition.

It’s been a crucial part of growing my business and building long-term relationships in what can sometimes be a lonely world of remote work. Sometimes your skills are more suitable for job opportunities than other professionals in your industry, and you will come across these opportunities by networking and building trust with others.

One day you might become a thought leader in the space, and that will keep you rooted in your industry for the long term. Not to mention the support and confidence building that can come with networking. So many times, you come across the same pain points as others in your network, and it’s a sense of “you are not alone” and “we get it.” Network, network, network!

Doug AshDoug Ash
Founder, Doug Ash Photography

Learn Essential Freelancing Skills

Having first freelanced from 2006 to 2008—and having done it successfully with basically only PayPal, QuickBooks, Microsoft Word, and Outlook—I wish I would have researched and learned the skills needed to successfully freelance when I returned to it in 2020.

I’m very fortunate to have a freelancing job for a digital media company in the insurance industry. Not only do they have enough assignments to satisfy the amount I want to work, but I’m lucky to have a manager who is a former teacher and loves to share resources and advice to help bring me into the modern freelancing world.

Without her guidance, I feel I would have been hindered from success because of my lack of knowledge, mainly regarding SEO but also including everything from WordPress to Google to Grammarly. It took me a while to catch up in order to have a better understanding of what clients are looking for and how to pitch that to them.

Michelle RobbinsMichelle Robbins
Licensed Insurance Agent, Clearsurance.com

Manage Your Freelance Tax Obligations

Unlike a regular job where taxes are withheld from your paychecks, as a freelancer, you’re solely responsible for setting aside money for taxes.

I recall my first year as a freelancer vividly; I was so engrossed in winning projects and executing them that the financial management side took a backseat. The tax season arrived, and the substantial amount I owed in taxes was a cold wake-up call. I had to scramble and dip into my savings to cover it. That was a turning point for me, highlighting the need to plan for taxes as diligently as for any project.

Since then, I’ve made it a point to regularly set money aside specifically for tax obligations, saving me a lot of stress and potential financial setbacks.

Ben McInerneyBen McInerney
Founder and Director, GoSolarQuotes

Focus on One Specific Niche

The one thing I wish I knew about freelancing before I started is the importance of consistency in one field.

While freelancing offers the freedom to work on various projects and explore different areas, specializing and consistently working within a specific niche can greatly benefit your career. It allows you to build expertise, establish credibility, and attract clients who are specifically seeking your skills.

Focusing on one field from the beginning would have helped me establish a strong foundation and position myself as an expert in that area, leading to more opportunities and long-term success.

Irina PoddubnaiaIrina Poddubnaia
CEO, Founder, TrackMage

Embody Continuous Learning

I wish I knew the importance of continuous learning in freelancing before I started. The freelance marketplace is dynamic, and staying updated with industry trends, learning new tools, and improving your skills are paramount.

For example, a freelance graphic designer might need to stay abreast of the latest design software. This continuous learning and upskilling not only makes you more competitive but also opens up new opportunities in your freelance career.

Aysu ErkanAysu Erkan
Social Media Manager, Character Calculator

Practice the Art of Self-Promotion

One thing I wish I knew before embarking on the freelancing journey is the value of self-promotion. As a freelancer, you are your own brand, and marketing yourself effectively is as crucial as delivering high-quality work.

This might involve creating a professional website, networking, and leveraging social media. Self-promotion helps expand your client base, command higher rates, and ultimately succeed in the competitive freelancing market.

Dilruba ErkanDilruba Erkan
Consultant, Morse Decoder

Persevere for Freelancing Rewards

After freelancing for 11 years, I’ve made so many mistakes I stopped counting.

But one thing I wish I learned before jumping into freelancing is how much it’s worth when you make it.

You will likely fail endlessly, but you need to learn from your failures because I cannot emphasize enough how rewarding it is to be a freelancer. I manage my schedules, times, and locations. However, the freedom to travel to another country and work for a month is unbelievable.

So whenever everything seems harsh and dark, remember why you started freelancing and your goal. Once you get through the first tough months of freelancing, you’ll understand why it was all worth it.

Phillip StemannPhillip Stemann
Freelancer, Phillip Stemann

Value Your Time and Expertise

As a freelancer, it can be tempting to say yes to every project or accommodate clients’ requests without considering the impact on your workload and well-being.

Understanding the value of your time and expertise early on is crucial. It’s essential to define your scope of work, set realistic deadlines, and communicate your availability and limitations to clients. This helps establish a professional relationship built on mutual respect and ensures that you can deliver high-quality work without sacrificing your personal life or burning out.

Learning to negotiate contracts, set fair rates, and enforce payment terms are also important aspects of freelancing. Establishing clear communication channels and having a contract in place can help prevent misunderstandings and protect your interests.

Luke LeeLuke Lee
CEO, Ever Wallpaper

Educate Yourself in Financial Planning

One thing I wish I knew before starting freelancing is the importance of financial planning. Understanding the need to budget and plan for irregular income, taxes, and business expenses is crucial.

Freelancers often experience fluctuating income, and it’s essential to have a financial cushion to manage lean periods. Additionally, being aware of tax obligations and setting aside funds for taxes is crucial to avoid surprises and penalties. Creating a budget, tracking expenses, and planning for both short-term and long-term financial goals are essential for the financial stability and success of freelancers.

Jason CheungJason Cheung
Operations Manager, Credit KO

Prepare a Backup Plan

When freelancing, it’s important to remember that much of your success relies on the fluctuating demand for work. As such, it’s wise to have a backup plan in place for when work is few and far between.

This could involve having emergency savings or taking on side gigs that you can utilize when times get tough. Additionally, it’s beneficial to build a strong network of contacts who you can turn to for help if needed. By having a backup plan in place, you’ll be better prepared to handle the ebb and flow of freelance work.

Darryl StevensDarryl Stevens
CEO, Digitech Web Design

Establish Expectations Upfront

Freelancing is awesome. It offers heaps of benefits, like flexibility and improved work-life balance, but it can also blur the line between work and personal life if boundaries are not set from the beginning. If you’re starting out freelancing, here are a few things to consider (that I wish someone had told me when I first started!)…

Clearly define the hours you’ll be available for work and communicate them to your clients. This helps manage expectations regarding response times and ensures that you have dedicated time for personal activities or rest. You need to schedule time off for yourself. It can be very easy to be glued to your emails 24/7, but over time you will burn out.

Also, make it clear to clients how and when they can contact you. Establishing these expectations upfront can help avoid misunderstandings and reduce stress.

Nicholas RobbNicholas Robb
Founder, Design Hero

Submit Your Answer

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