10 Lessons from My First $100,000 on Upwork

January 17, 2023 – The Day I reached the milestone of making $100,000 on Upwork. It’s a special moment, I feel very lucky to get there, and I know there are 100s of freelancers who are working hard and making $100K is certainly an aspiration that they all share.

Of course making $100,000 on a freelancing platform is just a milestone and not the end goal, but getting there, is an achievement worth celebrating. (Which I did with my family, and a lot of gratitude)

But this post is about lessons, things that I have learned from my experience as a freelancer on Upwork, my journey of making $100,000.

Although I think you learn something new every day, and each day can teach you something that helps you become a better version of yourself at whatever you do. The 10 lessons that I want to share with you, will help you focus on the things that work well to become a successful freelancer, although these lessons can be applied to other freelancing platforms, my specifics would be about Upwork, as that is where I got a bit of success. 🙂

And finally, before we get onto the 10 lessons, a bit of a disclaimer! These lessons are from my personal experience, my journey of making $100,000 on Upwork as a freelancer. These are not shortcuts or quick hacks to making $100K (I don’t think there are any), and certainly I do not believe that one should follow another’s path, everyone has their own journey, the lessons are there only to learn and apply on your way as you go and as you deem fit, and not copy paste. I hope this made sense, if not, feel free to comment below and I’ll be happy to answer your questions.

1. Go for the Big Fish Clients

Credit: Pexels

I think Robert Kiyosaki in a video once said – “Money is in the Money”. Meaning if you’re working for a client that is making a lot of money, it will be easy for them to pay you at a decent rate versus a client that is trying to establish their business or struggling to be profitable.

So be always on the lookout for jobs by clients that have spent $100K or more, especially at a decent hourly rate. Put a little extra effort to your job proposals for these clients, make sure you stand out, do a bit of research on them, learn about them from their past jobs, feedbacks and profile, you can also look them up on google or linkedin, find as much as you can about what you can write in your cover letter that will capture their attention and make them consider you as a strong candidate for their job.

Although you might feel that your profile is not strong enough for this, maybe you just have a couple of jobs and have not earned much or don’t have many 5 star client feedbacks on your profile, but do not let this stop you from giving your best to get this job.

I understand it can be tough to get with a blank profile, but if you have done a few jobs already, and you have good communication skills, you can land the job.

It was only my 4th client, within my first month on Upwork that agreed to pay me $1000 for only a couple of hours of work. And after completion of that, we got into a long term contract and worked together for several months. Which brings me to my second lesson!

2. Build Long Partnerships

Long work collaborations with the clients are an absolute key to making money as a freelancer. You’ve got to work on building a strong work relationship with your clients that lasts long.

Think like this, you’ve done the toughest task of getting the job, among hundreds of freelancers, the client have picked you to do their job, so all you need to build a long lasting work collaboration is do your job well.

So, give it your all. Try to understand their pain points, comprehend the requirements and deliver to your best protentional. Be flexible for revisions & rework, listen to their feedback, try to incorporate it. Your goal should be to make them happy and produce quality work, that not only they stick to working with you for their next project, but also recommend you ahead.

Always stay transparent, communicate frequently and appropriately and try to deliver extra than you promised. A client will only keep on working with you if you offer them value more than what they are paying you.

3. Communication is King

Communication is the number 1 skill you need to have for success as a freelancer. Of course it helps in life as well but we’ll stick to freelancing here.

From a strong profile to a captivating job proposal, and of course the hiring interview, you will need great communication at each and every pivotal point of freelancing.

Even when you’ve got the job, communication is important throughout. Make sure you are available for communication on the set hours and especially at the beginning of the work collaboration, because that is when client does not know much about you, so the relationship is at a vulnerable stage, but even when you have worked together for long, good communication is key for a happy client.

And do not take this lesson as you have to talk a lot with your client or communicate every day, but rather make sure that both parties are in sync and align with the expectations and the deliverables.

Simple and to the point is always the best way to get your point across.

Guy Kawasaki

4. Do Not Depend

One of the major reasons we go for freelancing, is we want to be independent. But as we get few contracts going, we start to depend on our existing clients and slow down our hustle for getting new clients.

Consider a scenario where you have a decent profile, you have a good rapport going on with a client, you’re making good, consistent money, and you start to rely on that client for your regular freelance work and income. That’s a BIG NO!

Relying on a client is a regretful mistake that you cannot afford. It goes against the core values of freelancing. So, no matter how good you think you’re doing on a job, do not be depended on it. Always keep your hustle going, be on the lookout for finding new work, it’s the key for a sustainable freelancing career.

5. Build a Team

Although you can earn pretty well doing it all alone, but that’s going to limit you a lot as well. I remember at one point, I was working around 16 hours day. But you don’t want that (no one wants that, even if you’re making $1000/hour), because that is not viable.

You want to live too, you need time at your hand, you want to spend quality time with family, friends, go out, travel, these were all the perks that attracted us to freelancing right? And to get all these, you must work on building your team.

Find people who can work with you, train them to be the best at what you want them to do, and delegate your work. Hire specialists, experts at the services that you’re offering and share the load.

I’d also like to share a few key points regarding building your time that you should note.

  • Expertize: Try to hire people who are good at what they do, and train them to be as good as you are if not better. The quality of work your team is going to produce, your profile and portfolio will be impacted by that. So make sure, your team only helps in elevating it.
  • Lead: Instead of just being an employer, manager or their boss, try to be a leader of your team. Leading means that you will help them grow, not just in their skills but also as a person. Don’t try to hold them back in hopes that they don’t move ahead or take on another job or even start someone of their own. Your role as a lead should be to help them achieve their desired goals, even if that means that they desire to outgrow you, you should be a support for them and their success will be an award for you.
  • Share: It’s very critical that your team stand by you, and to achieve this, you must share your success with them. And not just celebrate it with them but also reward their efforts with financial sharing. Paying a set salary or percentage, whichever you are contractually bound to, is not included in that. Go above and beyond, when you make more money, when you achieve a milestone, when you are rewarded with a good contract, make sure to share some of it with your team also.

6. Decline Offers

Yes, you read it right. This one is very important to learn, and I can understand, it will be a tough one but believe me, you will have to learn saying NO and decline job offers.

From my experience, I work to the best of my ability, regardless of the rate that I am being paid or the contractual monthly amount for the service, so for me, there is no benefit of a $1000/month job vs a $500/month, so why work for less?

Your time is same, once you value it at a certain point, do not undersell it. Decline offers that are lower than your set rate.

And it shouldn’t be just about the financial value of it, also consider this for the peace of mind. If you are getting a vibe that the client likes to micro-manage, it’s better to say NO now vs getting into the contract and then wishing you hadn’t.

Same goes for any other factor that you feel does not work well for you, maybe you don’t want a weekly meeting or a daily scrum, do not try to sacrifice or compromise on the things that work good for you or make you happy, because in the long run, you won’t be able to hold-off of those and that will be a miserable work routine.

So, when in doubt, say no, decline the offer and move on.

7. Get Better

No matter which skill set you have and what services you are offering, how good you are and how much experience you have, you need to be always working on yourself to improve it. Keep honing your skills, keep up with new stuff, train yourself to be better than yesterday.

It’s really easy to think and be under the impression that you are quite good, especially when you’re earning a decent money, but that should never stop you from trying to get better at it.

Whether it’s graphic design, creative writing, social media marketing, SEO or whatever skill that you are offering, even if you’re just a VA and doing data entry or scraping the internet, you must try to improve yourself at it.

A few ways to improve yourself:

  • Connect: Get in touch with people who offer similar skills, you can also use Upwork’s network feature or groups on Facebook.
  • Learn: Youtube, Udemy, Masterclass, or any other, make sure you spend some time on learning from the experts of your skills on these platforms.
  • Follow: There are top of the line, credible content publishers and websites about almost all of the skills, follow them. Blog, Podcast, Forum or reddit, whatever it may be, you should be following them to stay up to date with the industry trends and everything new and coming.

8. Value Yourself

Remember that idea of freelancing that got you here? Being your own boss, work from anywhere you want to, flexible timings, unlimited vacations. Well, you cannot get all of these, unless you work for them.

You need to value yourself correctly and appropriately. What do I mean by valuing yourself?

  1. Price your time well. Do not sell yourself cheaply, if you think you are good enough and produce quality work that your clients appreciate. Whether you think you deserve $50/hour or $200/hour, whatever it may be (of course, it has to be market competitive of your industry. Look at top profiles of your skill set to review how your competitors are pricing their work.), price your service well and stick to it.
  2. Money is just one aspect of it, value your free time also. Make sure to set your availability appropriately, even if you have a team, you shouldn’t overburden them also. It’s better to have people on your team with a couple of free hours a day than to have them work an extra hour each day. Just as you will appreciate more free time and holidays for you, so will your team.
  3. Set boundaries between your work life and personal life, make sure you also have a personal life, and are enjoying it. No point over stressing over work and money, when you don’t enjoy the life you are struggling for. Every now and then, pause, reflect, live.
  4. Celebrate your success, appreciate the people you have, show gratitude. These are all the ingredients for a happier self, more than the money and milestones, focus on the small things that make you happy.
  5. Stop comparing yourself to those Instagram lives, those Ferrari quotes, the so-called self proclaimed mentors, don’t fall for those rabbit holes. Focus on things that would matter to you if no one else in the world would care, those are the things that you should strive for.

9. Take on Failures

Failures will be part of every path worth traveling, so don’t take them to your heart, rather learn from them. Losing a job that you’ve worked hard for, or a team member that you have trained well, no matter the type or the scenario of the setback, you can bounce back from it, and much stronger too.

As our Billy has said;

It’s fine to celebrate success but it is more important to heed the lessons of failure.

Bill Gates

Another quote that I think one should have as a frame in front of their work desk is

Failure is delay, not defeat. It is a temporary detour, not a dead end.

Denis Waitley

10. Enjoy

Don’t you dare think that this is the end of the list and I am out of ideas for anything deep and motivational to say and just trying to complete my list of 10. Enjoying is just as important as any other lesson on my list, certainly it is for me.

Freelancing is a challenging career choice, with all it’s perks and fancy lifestyle that it is showcased to be, it comes with a price. Price of being always on the edge, the hustling life, the all-nighters, the questionable looks, and not so friendly or supportive comments from the people around.

Don’t pay much heed to the negativity, wear blinders and focus on what you want and what you need to do in order to get what you want.

My acting teach at BNU used to say, you must always ask yourself the following 3 questions.

  1. Who are you?
  2. What do you want?
  3. What do you do to get what you want?

Even though the exercise was to get into a character for the acting assignment, I think you should have the answers to these questions quite clear for yourself as well.

Final words!

This is it, these are all the 10 lessons that I think worth sharing with you all from my freelancing journey of making over $100,000 on Upwork.

I will try to keep updating this post as I learn more, and if you have anything to add, please share in the comment below.

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