How Freelancing Is Like Dating

I had my first experience freelancing on a whim. For months, I’d been working as a writer within a startup that was struggling to get off the ground.

After the company got acquired by another startup, I looked for jobs but couldn’t find any that met my deep-seated need to write about useful things like how to travel using points and miles or how to hire better people for your business.

So, when an old college friend emailed me about doing freelance work for them, I jumped at the opportunity. Yes, it was scary (I’d never done freelance work before), but it felt like something I needed to try out anyway.

Since then, I’ve worked with other companies in various capacities as a freelancer and learned some valuable lessons along the way. Here’s what you should know if you’re considering becoming a freelancer or hiring one:

Takeaways
Freelancing and dating share commonalities in terms of challenges, uncertainties, and rewards.
Both freelancing and dating require perseverance and a long-term commitment.
Freelancers, like daters, need to navigate the ups and downs of their respective journeys.
Flexibility is a key aspect of both freelancing and dating.
Building relationships and connections are essential in both freelancing and dating.

It Takes Time To Find The Right Fit

Like dating, finding the right fit can be tough. You have to find someone whose goals and methods are similar enough to yours that they don’t crash but different enough that they can bring something new and exciting to your life.

In freelance work, this means you need to find clients who understand what you do and how you do it and are willing to pay for it! The good news is that just like dating, there are plenty of options out there for anyone who wants them.

The key thing about finding a good match is knowing what kind of person or company would be a good fit for you. If their values align with yours (or even just their needs), then chances are things will go smoothly from day one.

Navigating the ups and downs of freelancing can be a transformative journey. In my personal experience, freelancing has been a lifeline. It has provided me with the freedom to pursue my passions, embrace flexibility, and regain control over my career path. Discover how freelancing can have a profound impact on your life by exploring our article on how freelancing saved my life.

Freelancing Requires A Lot Of Self-Marketing

Another major difference is that you need to be able to market yourself. When it comes down to it, freelancing is all about being able to work for yourself and make your own money which means you have to make sure clients know who you are and what you do so they can hire you. 

You’ll have to market yourself both as an individual (whether through websites like these or in-person) and as a business (through websites that help companies find reliable freelancers).

It’s also important for freelancers not just to try selling themselves but also to each other because doing so will strengthen their community.

Don’t underestimate the power of networking: by helping out other freelancers with their own self-marketing efforts via social media or word of mouth referrals, they’ll likely return the favor one day when they’re looking for someone else’s services!

Clients Are Emotional

Unlike your boyfriend, a client is a person. They have feelings, and sometimes those feelings can be emotionally happy, sad, or angry.

Sometimes they’re stressed out or overworked. Sometimes they’re hungry or tired or distracted. If you want to build a good relationship with your clients then you need to understand that they are people too!

You should be aware of how other people are feeling in order to communicate effectively with them (and avoid miscommunication).

It Can Be Hard To Get A Real Commitment From Clients

The second thing you’ll notice as a freelancer is that it can be hard to get a real commitment from clients. It can feel like you’re dating, but with the other person playing games and wanting things to work out in their favor.

Clients aren’t always reliable either; sometimes they just disappear altogether without any warning or explanation. They may also demand things that are outside of your skillset—or even worse, make changes midway through the project without much thought for how those changes will affect the whole process or timeline!

Freelancing is often romanticized as a quick path to success, but the reality is that it requires perseverance and long-term dedication. Just like running a marathon, freelancing demands endurance, pacing, and strategic planning. To gain valuable insights on navigating the freelance journey, delve into our in-depth article on why freelancing isn’t a sprint but a marathon.

Sometimes, It’s All About Timing

There’s no better time to find a new job or freelance gig than when you’re already busy with another project. But that means you’ll need to be flexible, willing to try new things, and open to new opportunities. 

And if the timing is right for a new job or freelancing gig? You’ll need to be willing to adapt, change and learn new skills, and maybe even take some risks. The bottom line: Sometimes it’s all about timing!

If Your Timing Isn’t Right, You Can Still Be Friends

One of the most important things to keep in mind when freelance dating is that if your timing isn’t right, you can still be friends.

It’s not always easy to find a new client, or it may take some time before you realize that someone is no longer a good fit for you to work with. But if there’s mutual respect and understanding, sometimes that’s all you need.

That said: If it feels like something isn’t working out, don’t be afraid to let go of that person and move on. If they’re not happy with how the relationship is going (or vice versa), then maybe it’s better for both parties if they part ways now rather than later.

You Have To Be Willing To Try New Things (And Hope For The Best)

I once saw an article that said if you want to find out what someone is like, ask them about their worst date. It’s so true. The same applies to freelancing. If you want to succeed and make it as a freelancer, you have to be willing to try new things, and sometimes that means failing.

If something doesn’t work out for me and my client after I’ve done my best work on it, I have no problem accepting that fact because I know that means one thing: next time will be better. You can’t learn unless you try. And the more times you fail at something the more likely you are going to succeed at it in the future.

The traditional 9-5 workday is being challenged by the rise of freelancing, which offers a flexible alternative that empowers individuals to shape their own schedules. Embrace the changing landscape of work and explore the ways in which freelancing is disrupting the 9-5 paradigm by reading our insightful article on how freelancing is disrupting the 9-5 workday.

Sometimes The Grass Is Greener On The Other Side (And That’s Okay)

Sometimes, it’s okay to try new things. Sometimes, you may even find that the grass is greener on the other side.

It’s not always easy to switch jobs and companies, but there are many reasons why freelancing is like dating: it’s a better way for you and your client/company to get acquainted with each other before jumping into something serious.

Some Jobs Require More Maintenance Than Others

Some clients are more demanding than others. Some jobs are more challenging than others. Some clients are more challenging than others, and some jobs require more maintenance than others.

Some freelancers know how to work on a team, while others prefer working solo or in pairs/groups of three or four. Some freelancers like being called upon for specific projects, while others want regular gigs with consistent paychecks.

There isn’t one right way for all freelancers to operate; it’s all about finding what works best for you as a freelancer!

The Best Part Of Freelancing Is The Freedom And The Worst Part Is The Freedom

There’s nothing like the freedom of working from anywhere, and freelancers are lucky to have it. But this freedom is also a double-edged sword: it can be hard to know when or how much work is enough.

It’s up to you as a freelancer whether you want to take on more clients or not, but remember that there will always be more opportunities out there even if they’re not exactly what you want or need right now.

And while having control over your schedule is great, sometimes finding time for yourself can feel like an impossible task between client deadlines and all the other commitments in your life.

More Than You Expected, Sometimes

Have you ever been in a relationship where you thought it would be one thing, but it turned out to be something else entirely?.

And then, when all was said and done, did you look back and think: “I’m glad I got to experience that.” If so, then congratulations you have a sense of perspective on relationships that is at least as developed as your ability to make good money as a freelancer.

Freelancing can be hard work; there’s no getting around that. You might get hit with multiple deadlines that all need to be met or exceed expectations by substantial margins within the same week. You may spend hours upon hours working on projects just to realize they’re not worth their weight in gold or even silver (or even bronze). 

And yet and yet you will also discover hidden joys in tasks that seem mundane at first glance. For example: editing someone’s business plan (that has 37 typos) can actually be pretty fun if you’re into grammar and spelling!

Sometimes It Feels Like Everything Is Off-Limits

Sometimes when you’re freelancing, it feels like everything is off-limits. You may be questioning your skills, wondering if the project is even worth taking on in the first place. You may feel like you’re too inexperienced to do this or that your skills aren’t up to par with what they should be. 

In these moments of self-doubt, it’s important to remember that you have agency over whether or not something works out. No matter what happens with a project or client whether they appreciate your work or not you still have control over whether or not it succeeds for you and those around you (including future clients).

Sometimes all an artist needs is a little encouragement from someone who understands their struggle: “I know exactly how you feel because I’ve been there before!” That’s why sometimes it helps when another person can say something encouraging at just the right time.”

The freelance revolution is reshaping the workforce and becoming increasingly mainstream. More and more individuals are choosing freelancing as a viable career path, seeking freedom, autonomy, and the ability to work on their own terms. To explore the reasons behind this shift and gain a deeper understanding of why freelancing is becoming more mainstream, dive into our comprehensive article.

It Can Be Great, But Also Overwhelming

Freelancing can be great, but it can also be overwhelming. There are so many things to consider when you’re freelancing: who will hire you, how much they will pay you and when they will pay you. But if you stick with it and stay organized and focused on what is important to your business, the rewards are worth it.

Freelancing can be a rewarding career, especially for people who don’t want the traditional 9-5 job or need more flexibility in their schedules. It allows them more time with family and friends as well as pursuing other hobbies and interests outside of work hours.

Sometimes You Need To Turn Around And Walk Away

It’s a little sad when you have to turn down a potential client, but sometimes it’s the right thing to do. You may not be able to work with them because of scheduling conflicts or budget issues, or maybe their work ethics are just too different from yours. In any case, you’ll probably feel better about saying no if you know that it was for the best.

Like dating apps where users swipe left (no) and right (yes), freelancing can often feel like a numbers game: how many people will reject your offer before someone accepts? How many times will someone lose interest before they find their dream partner in life? 

It’s not always easy to walk away from something good but sometimes walking away is what’s best for everyone involved.

The Experience Varies Widely Within The Community

You’re not going to meet a freelancer who’s exactly like you. The freelancing community has a huge range of people, and each one brings their own experiences and personality to the table. Each freelancer is different. Some enjoy their jobs, while others struggle. 

Freelancers can be introverted or extroverted; they might work at home or in an office setting and they may enjoy the freedom of working on their own schedule, or perhaps they prefer more structure.

some are happy with just an hourly wage for their efforts, while others prefer profit-sharing deals where they get a cut from any income generated from the project the list goes on and on.

As you travel through this world of abundance as a freelancer, you’ll encounter all sorts of personalities along your journey: some positive experiences will stick with you forever; other times it might feel like everything is falling apart around you (and then again sometimes nothing bad happens at all).

As the popularity of freelancing grows, so does the number of freelancing platforms available. However, it’s essential to consider the safety and security of these websites before diving into the freelance market. If you’re wondering about the safety of freelancing websites and want to make informed decisions, explore our article that addresses the question: Are freelancing websites safe?

Final Thoughts

Freelancing is like dating because freelancers and clients need a lot of chemistry for things to work out. You need to see eye to eye on many fronts, and you both have to be confident that you can work together in a professional way.

Just like relationships, not every client is going to be a good match, which means that you’ll have to learn how to break up when the time comes. And just like dating, it takes time to find the right one.

Further Reading

Here are some additional resources on the topic of freelancing and its similarities to dating:

Freelancing and First Dates: Discover the surprising parallels between freelancing and dating, exploring the challenges, uncertainties, and rewards of both endeavors.

10 Reasons Why Freelancing Is Like Dating: Uncover ten compelling reasons why freelancing and dating share commonalities, shedding light on the dynamics and experiences involved in both journeys.

Why Freelancing Is Like Dating: Dive into the analogy of freelancing and dating, understanding how the process of freelancing mirrors the various stages of romantic relationships.

People Also Ask

Why Do You Like Freelancing?

Freelancing is like dating in that it’s fun, it’s exciting, and it can be a little scary to take the plunge. You know that there are some things you need to do (like getting a business license or insurance), but you don’t know what all the rules are yet. But once you start doing it and getting feedback from clients, it gets easier and easier!

What Do I Need To Get Started?

You need more than just a good attitude you also need the right tools to make sure that your business is running smoothly. 

In addition to a business license and insurance, here are some other things that freelancers need:

• A computer with internet access and good software.
• A phone (or even better, a landline) so clients can reach you easily.
• A printer/scanner/copier if necessary (many offices have one).

If I’m A Freelancer, Should I Date Someone Who Has A Different Type Of Job Than Me?

It depends on whether or not you’re willing to compromise your work-life balance. If you’re just looking for something casual, then sure! But if you’re looking for something more serious, then you might want someone who has similar goals and values as you do.

How Do I Know If Someone Is Right For Me?

There are so many ways! You could ask them what their favorite color is (and if they don’t have one, they might not be as creative as you need them to be).

You could also ask them what their favorite TV show is (and if they say “Friends,” they might not understand how important creative freedom is). Of course, there are other ways too but these are just two suggestions!

What’s The Difference Between Freelancing And A Regular Job?

Freelancing is like dating you have to be ready to date, and you have to be ready to be alone. That might sound surprising, but it’s true.

Many people come into freelancing thinking they’ll have a lot more freedom than they do in a regular job. But the truth is that being your own boss means having to work harder than ever before, and sometimes you don’t even get paid for it.

Freelancing can also be hard because there are no HR rules or company policies to guide you. You will have to make all of those rules yourself (and enforce them). That can be scary at first, but the more experience you get, the easier it gets.

What Skills Do I Need?

The most important skill for starting out as a freelancer is persistence. You need to keep going even when things are tough, and even when people aren’t paying attention or wanting what you’re selling. 

Don’t give up. The world needs more people who believe in themselves enough that they can make something happen with their own hands.