Upwork case study: this reader earned $30,000 in his first year freelancing

A note about this Upwork case study: this is a guest post from a reader sharing his experience during his first year freelancing.

In early 2018, I decided to quit my job at a well-known market research firm. I was living and working abroad, with an average salary, but low levels of job happiness. 

During the last three months at my job, I decided to start freelancing to create an alternate income stream for myself. I was a business analyst by day, and a content writer/marketer at night (and on weekends).

In three months of this part-time freelancing, I was able to match my corporate salary (cue resignation letter). 

To reveal some numbers here (with some hesitation), my salary was $13,000 per year. After quitting my job and doing freelancing full-time, I was able to increase my annual income to $30,000 yearly (~2.5x).

This is a long blog post, and it’s for people who’re serious about making changes in their lives. I am not writing a prescription here, but sharing my journey, especially my learning (what worked, what didn’t) with the hope that some readers will find some points useful to make their own Upwork case study.

Why I chose to freelance over a stable corporate job

In my corporate job, I had a growth ceiling (10-20% increment per year). After moving to freelancing, my financial growth was only limited by my imagination. 

Depending on where you start, 20%-1000% or even 5000% growth is feasible. It was pretty straightforward, the more I pitched for projects, the more projects I converted and hence, the more I earned.

Let’s say, I’m looking to make an extra $2000, so I can go on holiday in Turkey, I know that I have to start pitching more to land an additional project. My cold pitch conversion rate might be 5% (e.g. I convert 1 out of 20 pitches into a paying client), so to land another job, I need to do 20 sales pitches. 

Imagining larger financial growth and attaining it has become easier for me in this job, where the correlation between my work hours and income is high, which wasn’t really the case in my corporate job.

Geographical freedom: In October, I was tired on a Friday evening and wanted to go out and party. However, my friends had no plans of going out that night and I was just so burnt out, I wanted a stiff drink and some solid music. 

I was chatting with this friend of mine, who lives 1 hour away by flight, and cribbing about how I was getting bored and wanted to do something. 

At 5:30 pm, she jokingly asked me to join her party. 4 hours later, we were sitting together in one of her friends’ living room, pre-gaming before heading out for the night.

In 4 hours, I had decided to spend the weekend there, packed a weekend bag, bought a ticket at the airport and took off.

There’s no fear of coming back to the office the next day. There are cafes there, right? 

I’ll just work out of one of them. This is a privilege that makes all the freelancing hustle worth it, the ability to have an option to go anywhere, whenever I want to.

In May, I spent two weeks in Vietnam, visiting my best friends there. I hadn’t seen them in over a year, so I moved my base for a few weeks and just worked out of cafes while hanging out with them in the evening.

While to many this will sound like I’m bragging (I might be just a tad), what I want to shine light on is that this is achievable by most of us. 

This isn’t for a select few lucky people or ultra-talented people, this is a choice of lifestyle we can all make, and develop a career like this for ourselves.

Freedom to work on my own terms: Having a higher bargaining power has been a pretty cool benefit of this working model. 

I choose my own clients and pick only people I enjoy working with and feel like they could be a good fit for me. I don’t HAVE to take clients on just because of money, but I can go beyond and talk about the quality of collaboration, etc.

Field report: What helped me achieve these results and this lifestyle?

These were KEY in helping me make this Upwork case study a reality.

Disciplined routine: It has become quintessential for me to have a disciplined routine. I kept hearing about discipline and maintaining a strict routine, but it felt more restrictive than productive. 

It felt like a boring, herculean task that great entrepreneurs and high power people did, but not normal people like me. 

However, the joys of not having a routine were very short-lived. Soon (read within weeks), my productivity started to plummet and mental peace was disturbed too. 

This made me realise that maybe the routine I thought was restrictive was actually for my own benefit, and to save me from my lizard brain.

After working on creating one for myself (and failing countless times to stick to it), here’s what the core elements of a disciplined routine include for me:

1. Fixing my sleep cycle and adhering to it
2. Fixing my eating routine and adhering to it
3. Meditate everyday
4. Regular workout routine with a personal trainer
5. Taking cheat days to break the monotony

With these five points, I have been able to discipline my routine pretty well as compared to before. 

I’m not saying this is a formula, this is just what has been working for me, and maybe a combination of these (or some other activities) might work for you. But to shed a little light on how this works for me, here’s what I do:

• I sleep at 10:30-11pm every night and wake up at 5:45-6:15 am
• I workout with my personal trainer from 6:45 until 8 am (at least 4 times a week)
• I eat my breakfast at 8:30 am, lunch at 12:30-1pm, and dinner at 6:30pm-7pm
• Every morning before breakfast, I sit with myself for 15 minutes and meditate. I’ve been using the Headspace app, which has been working really well for me, and it helps me relax, since anxiety is a pretty commonly occurring phenomenon among a lot of us
• I take cheat days where I let my routine go to shit! Usually this happens once a week. Maybe I’ll stay out late one night, or skip workout for a day, or something like that. It helps me break the monotony this way too, which makes me not feel like a complete robot

With these few anchors, I’ve been able to develop a disciplined routine which has been proving itself to be a great strategy for maximising creativity and output capacity.

Learning to sell: While working on your routine and mental health is of high importance, that alone might not be enough to help you convert more prospects into clients. 

What the prospect sees directly is your sales pitch, so fine tuning that and learning how to improve them is a default given.

These few things helped me improve my sales pitches over time:

1. I took inputs on my sales pitches from experts in my industry who knew how to pitch, and were visibly converting a lot of clients. Their inputs were sharp, very focused, and helped me learn about the concept of offering value instead of skills.
   
   My pitches now tend to focus more on helping solve real problems, whereas earlier I used to talk more about what I could do and why I was the best at what I did. The focus is slowly shifting from me to them and solving their problems.

1. Pitching a lot, pitching consistently, and being okay with failing pitches helped me improve so much. I did a lot of bad pitches. I still remember having beads of sweat trickle down my back some years ago, when I was on a call with a prospective client, and was just unable to answer his questions, feeling super under-qualified like an impostor and unprepared to face a barrage of questions like these.
   
   In retrospect, his questions were just so normal, and he was just trying to clear his doubts, but for me at that time, he was challenging me and doubting my skills (haha!). 

Focused on developing and specialising in one core skill first: In the first year as a marketer, I realised that it’s very tempting to test out multiple channels and try and sell all these channels to different types of customers. 

For example, one could be a Google Ads expert, Facebook ads expert, ManyChat bots expert, along with Bing, Pinterest, Snapchat ads, SEO, and Shopify website development.

However, thanks to some great advice from a friend, I decided to stay away from multiple skills and chose to pick projects only in Facebook ads. 

In retrospect, what it gave me was an opportunity to work on bigger projects as a specialist, because now I was an expert in this particular niche. 

After a year, I have the liberty to add another skill to my arsenal, and now I don’t need to start at the bottom; I already have bigger clients, and I can start pitching these skills to my larger clients. 

I love what Ramit Sethi once said about his approach to his business. People asked him why he wasn’t getting on to multiple other channels, and why was he so focused on his email funnels.

He said he knew there are multiple potential channels, but that he wanted to fine tune his email funnel first, and make it amazing. He willingly let go of multiple other channels just because he wanted to really master one before moving to the next one.

The power of having a solid pipeline: As a freelancer, you might have been faced with situations where you’ve had to make compromises on the price for a particular project. Even though you priced yourself higher, you had to come down because you really needed the project to hit your targets.

Having a solid pipeline, where you’re constantly on calls with prospective clients at least 5-10 times a week, and converting 1 every week, gives you the power to turn down clients that you don’t wish to really work for.

If you’ve got 9 more calls lined up for the week, and 10 more next week, and the week after, your confidence will be high and you won’t make such compromises, which has been a game-changer for me.

What can you do to fill up that pipeline for business development? Are you tracking how many of those leads you’re converting? If not, start working on it yesterday!

In the first year, I feel business development could take 30-40% of your daily work, since you’ve got fewer projects and more time on your hand.

Weekly tracking of revenue and profits: I took this training with Jesse Elder, who’s a mindset coach. He taught me a great tool, which was a fantastic reality check for me. 

I always had a vague idea of how much I made in a month, but as a freelancer, bringing it on paper with regular tracking made a lot of difference. That clarity you get about your numbers actually helps drive you to get better at your numbers.

Here’s what a typical calendar looked like for me. I would record daily revenue and analyse how I performed that month, and then set a target accordingly for the next month.

Mindset Training: My mindset training has been crazy important for me. From listening to Chase Jarvis’s and Tim Ferris’s podcasts, to learn from Seth Godin about marketing and creating value, all of this has been hella important in giving me a healthy perspective towards work and growth.

I feel mindset plays 75% (arbitrary number to express importance) role in shaping my success, while my skill set plays 25%.

However, to get better at work, I always used to focus on sharpening my skills only, and hardly paid any attention on working on my mindset. The day I decided to make a switch, the following year saw an amazing bump in revenue, mental health, and confidence.

Optimize for learning in the first year: So I’ve picked a skill that I’m going to hone in on and stay away from other skills that can prove themselves to be distracting. 

But what’s my objective for this first year now? Do I want to make as much money as possible? Maybe! But what if I expanded my vision a little bit, and started looking at this as a 5 or a 10 year game, now what’s this 1st year going to serve as? 

I know I want to be making much bigger amounts later, so this year, even if I make $5000 extra, in the bigger picture in 10 years, it won’t make any difference. Hence, I focused more on putting my energy into learning instead of making more money.

Of course, I worked on making more money too, more than ever before, but at the core, I always stayed aware that making more money isn’t my primary objective. 

The primary importance was given to rich learning experiences. If I focused on building the right skills and the right mindset right now, I might give up on $5000 of extra income, but it will potentially make me hundreds of thousands of dollars in the coming years, and that’s what I focused more on.

I Invested in training myself: Buying courses for skills that you really want to develop and working week by week on those courses has paid off over the last 2 years. 

If you really trust some of your gurus, I’d recommend you to go forward and make a financial commitment to a course that you think might add value to your work. 

The bit about financial commitment here is super important because I’ve realised that this commitment makes your dedication towards the material much higher and one tends to follow through a lot after making such commitments.

Being OK with failure: If I could, I would write long chapters on this specific life lesson. The constant fear of failure is harrowing, and even though failure is an unavoidable outcome so many times, I used to do nothing to overcome that fear and got consumed by it. 

A simple shift in mindset made this SO much easier for me. If you’re trying something, there’s a chance it won’t work, and owning that life lesson and believing in it made all the difference. 

Now, I go into a project with expectations of failure. No, I’m not banking on my projects to fail, but here’s how my mental monologue sounds: 

“Okay, so I’m going to start blogging, and the first 10 posts might suck, but consistency and practice will make them better over time. There’s also a high possibility that it won’t be as useful to me as I am thinking right now, and I might have to scrap it later. The worst case scenario isn’t too bad. Cool, let’s test this!”

This thought process gives me momentum and helps me be less emotional about my failures. 

It doesn’t matter that 5 of my ideas fail. I’m learning how to put ideas into work; execution, I feel, is what matters more. 

If 5 ideas fail, that’s okay. Not all ideas will fail. One idea will hit the right chord sometime, and I’ll know how to put that idea to work and reap its benefits because I’m used to executing my ideas.

Otherwise, ideas are almost worthless if not implemented.

Please note that this isn’t a trial and error method either. I’m not executing every idea I get and hoping for a 10% success rate. 

What isn’t mentioned here is that I’ve already examined the idea and thought it through, and deemed it important enough to pursue to help me achieve my objectives.

After that analysis, I put it to the test by actually executing it consistently over a period of time, before assessing its future.

‘Let’s test this!’ This has become the central theme that helps me make decisions in life now, and tests can obviously lead to positive or negative results both.

Prioritization of tasks: I learned that there are 1000 things that are ‘nice to have’ but usually just 1 or maybe 2 things that are the next most important tasks to do (things that move the needle). 

The simple question I ask myself to help me prioritize is, is this the next MOST important thing for me to do? 

Whatever is the MOST important thing gets my attention, rest goes on the backburner for that moment. I am not saying I lose them, I just don’t attend to those tasks AT THAT VERY MOMENT.

Let’s loop in my blog’s example here. At the moment, I’m testing if I can be regular with writing and if my content can be useful to at least a small group of people who are creative/entrepreneurs. 

At this moment, I could get a flashy website and a great photoshoot done for the blog, but is that really the most important thing right now? NO. 

Can I do without it and test my blogging skills and get validation without the glitter and dazzle? YES! This is prioritization of what’s important right now and what’s not.

What’s MOST important for me right now is to publish, to publish regularly, to take feedback, and to improve: maintain consistency!

Sales is about a value exchange: A new bar opened up in my city, so I went to check it out. It’s a regular bar, it’s decent, they have a clean space, basically the same offering as other decent bars of the town, nothing crazy new. 

They’ve got good tiles on the floor, I’ll give them that, but apart from that, from ambiance to services to anything else, it’s pretty much regular. 

Yet, they charge me 2x the regular price of a beer that other bars would offer. I’m all for paying more for a good experience, but it’s the same beer, same city, same mood and feel of the place as any other bar. 

They’re literally offering me no added value, but want to place themselves as an expensive bar just based on their price.

Fast forward a few months, I went to this other club, and they charged me probably 4x – 5x the regular price of a beer. 

Is it exorbitant for a beer? YES! Did I mind paying that price? NO! Why? They offered me value. 

They have a club that’s very swanky, they have a good crowd, amazing light and sound system, a great DJ that night, and overall created a pretty darn fantastic experience. Now you want to charge me higher for that? Here’s my card, and keep the tab open please!

What does this have to do with marketing as a freelancer? EVERYTHING! As a marketer, my job isn’t to publish ads, get more impressions yata yata yata. 

Yes, those tasks are a part of my job, but my job is to make my client’s life easier. I am getting paid so I can solve their problems and add value to their business / life. 

Once this becomes my goal, my objectives go above and beyond just doing the needful tasks, and I become, as Jay Abraham says, ‘their trusted advisor’. They’re more than happy to pay a premium to their trusted advisor who adds value to their lives.

This one mindset has helped me have amazing conversations with my clients, that they might not usually have with their freelancers, but probably only with their internal strategy team members. 

This also helps me create more long term relationships with my clients, because my role isn’t just to run ads, or do some marketing campaigns, but to actually solve their business problems. 

I just leverage marketing tools I know to solve their problems. Who doesn’t want to keep a problem solver around?

From an Upwork case study: What I wish I had known when I was starting out

More financial literacy: So, I made 2.5x more money last year than I did the year before that. But do you know how much I saved? A whopping 5% of my annual income. Could I have saved more? Hell YES! Then why didn’t I?

I didn’t even know how savings worked, or the importance of securing my future. 

Instead, I spent my money on booking last minute flights to different cities / countries and going out to party, or a combination of both. 

There’s nothing wrong with traveling or partying (or name your vice), but the fact that I did all this before I secured my future is just appalling to me now.

Track your cash flow too. If you’re a freelancer, you know how many of us have messy cash flows. Irregular income with an erratic schedule, especially if you’re a new freelancer. 

I used to track my revenue and profits, but never my working capital and expenses. This year, I’ve started paying attention to my expense fields too. It’s not so I can restrict my expenses, but so I can be aware of my expenditure and plan my savings and investments accordingly. 

Cashflow is CRUCIAL if you’re a freelancer, you want to have a 6 months cushion to fall back on. To plan this, having a clear idea of how much you make, how much you spend, how much you invest and how much you save is important.

I control only my actions, not the outcome: Okay so I’m gonna plug Chase Jarvis in here again; because of him and one of his podcasts, I learned something amazing. 

When I have to set goals, my goals need to consist of action steps, not the desired outcome. Let’s look at an example.

I can’t control how much I’m going to make this year. 

What I can control is the number of pitches I make every day / every week. The more pitches I make, the more jobs I convert, and the more money I make. 

My desired outcome can be to make $100k this year (arbitrary number), but that’s not my goal. 

When I’m working on goal setting, it consists of action steps like I’ll pitch for more $2k retainer projects instead of doing $500 projects. I’ll make at least 2 new pitches every single day of the year etc. etc. You get the drill.

This lesson is something I’m still imbibing and learning. To be frank, I still mess it up many times, but it takes time to put such things into practice, and I’m happy that I am consciously making an effort towards it.

What has helped you grow in your freelance career? Also, if you had to talk about one major bottleneck that’s slowing you down right now and you’re consciously working on, what would that be?

Hrishi

Hrishi is a growth hacker who’s currently based out of India after having lived in the US and Vietnam. He’s been working on more freelance projects than ever before and has also now created a startup since Jan’19.

A Formula 1 fan, he’s hoping to cover multiple races (Azerbaijan, Monaco, Mexico, Brazil, Singapore, etc.) in the coming years, and is working on making his freelancing pay for all this!

To get in touch with Hrishi, find him on Instagram at @hrishisomani