I was re-reading my 2020 recap today. Really enjoyed it and I want to do it again. Let’s look back at this year and what happened in my journey as a wannabe entrepreneur.

Freelancing (May-December)

In April this year, I left my job. It was a good job, as a Senior Data Scientist, in a US company, working from Italy. I was paid well above the Italian average. I had stocks and bonuses, private medical insurance and various benefits I never used. Overall, I made more than €100k in 2022, and I was on course to make even more in 2023. I left it anyway. I feel like time is passing, and I wanted to prove to myself that I could be useful outside employment too. I also realized that I don’t have the energy to grow a side business and have a full-time job at the same time. Some people do, but I am not one of them.

Without a job and a salary, I started looking for freelancing opportunities. I already had some contacts from last year and started with an Italian client. Not much work, but it was a start. I kept applying to more jobs on Upwork, reshaped my LinkedIn profile and also paid for the Small Bets membership, to increase my chances to get some job opportunities and learn about building an online business.

In May, I got in touch with an Italian online school for Data Analysts and started to teach there until mid-July. It was a part-time gig, as I was only doing it for 3 days a week, 2 hours each. I worked a lot to prepare the lessons, much more than the hours I was paid for. In the end, this gig took a lot of my time (at least 2 full days a week) and paid less than €800 per month. Helping people to change their career trajectory was very rewarding, but financially it was a disaster. I will not do it again. Are all teachers paid this little? No wonder there are so many bad teachers around.

In July a friend of mine suggested me another gig with an Italian start-up. I started to work with them on some Data Analytics stuff. The rate is not amazing but the job and the team are great. I am still working with them. In August another opportunity came up, through the Small Bets community. More Data Science related, with another great team, a fair rate and a long-term commitment. In the meantime, I was also getting some more gigs on Upwork and was able to increase my rate and get more reviews there.

Over the last 8 months, I was in more than 50 between conversations and job proposals on Upwork. At the end of the day, only 6 of them turned into job offers. That makes it a 12% conversion rate, which doesn’t look that bad. Most of the rejections come from Upwork anyway, a tough platform.

I am satisfied with my freelance journey, but I think it should not take more than 50% of my time. Ideally, keeping at 2-3 days a week should leave me the time to pursue what I really want to do. Build an online business.


SEO experiments (June-December)

I was scrolling Twitter one day in April and this tweet by Danny Postma caught my eye. Of course, it’s half a provocation, but there are a lot of tips and wisdom in it. I decided to follow his recipe and build a couple of small bets, based on SEO. I did some keyword research, picked two promising keywords (Data internships and Stoic Quotes), built a programmatic SEO website around them, did a small PH launch, sat back and hoped for some traffic in the long run.

Unfortunately, I don’t think Stoic Quotes is working, as I haven’t seen much traffic coming to the website in the last few months. Sure, there are a few people who search for “stoic quotes” but very few land on my page and I have not been able to get to the first page on Google. Will I keep working on it? Probably not, but I want to keep it alive, to experiment a bit with marketing, UX/UI and see what happens.

Data Internships is doing better. I get more than 500 visits every month from search. I also have a newsletter of 150 people, where I send the best internships each week. I have been automating a lot of the website in recent months and I can comfortably run it working 3 to 4 hours work on it each week. I cannot complain, but it’s not all SEO. My newsletter grew mostly because of a couple of viral Reddit posts (one was taken down by Mods but not quickly enough). So, I have to do some marketing to grow it further. I think the product is useful, it helps a lot of people sort out the garbage that is on LinkedIn and find relevant job opportunities that would otherwise go unnoticed. I am passionate about it and I surely want to keep working on the UX and automation. There might be issues monetizing though. A few people I have spoken to, do not think that companies would spend money to advertise a position as a Data Intern. And at 150 subscribers, it’s not yet time to sponsor the newsletter. A couple of weeks ago, I got an email from someone who wanted to publish his internships on the website. I got all excited, set up a Google form and came up with a pricing plan. When hearing that the posting was not free, the person ghosted me. Not a great sign. In any case, I will put a big red button for companies on the site. I am set up now. Soon, it might make sense to start reaching out to companies on LinkedIn. I am still not sure if monetizing via job offers is my best shot. Maybe ads about Data Science Bootcamps or educational products will be easier to land.


Social strategy is important, especially now that I freelance and need to build a brand, however small. I have been not active on Twitter since February 2021 and in 2023 I decided to pick up from where I left off. I made an effort to write every week and take some time every day to comment on my favorite Indie Hackers’ posts. Some of the accounts I followed from 2 years ago are not tweeting that much these days, unfortunately. I loved to read Alex West, but he also took a break at some point. Other people like Andrea and Jon have grown a lot since 2021. They were consistent over the years and I hope I can stay consistent too.

In April, I started to tweet about my SEO projects, built in public and showed my earnings from freelancing every month. Some of my tweets got many likes, with up to 2k visualizations. In November, I even gained more than 100 followers in a couple of days after posting an article on my freelance experience (on my blog and Reddit). In the last part of the year, I started to schedule tweets too, making sure to keep commenting on my favorite accounts. It’s a pity that the Twitter Analytics is completely broken now, it would be nice to see what worked in these months. Next year, I will purchase the Blue and see if my reach increases more.

I also started to post on LinkedIn and kept posting on Reddit. LinkedIn was a surprise for me, I had never posted anything there, and I started to post, maybe once every few weeks. The posts were just a longer form of my tweets. Thanks to my network each of my posts got quite a bit of attention and many people I was not connected with started to follow me. I have now more followers on LinkedIn than on Twitter. I should focus more on LinkedIn in the next year. Reddit is probably my native platform at this point. I have never had so much success on any other social. It helped me grow Alfa Data, it was a source of inspiration for many ideas, and some of my comments got me hundreds of likes and many DMs. The post about my first 6 months as a freelancer got around 200k views, more than 500 upvotes, 100 comments, and so many DMs it was hard to keep up with it. But most importantly, it gave me a signal, about what people are interested in hearing from me. Since November, I have almost exclusively tweeted about my Data Science freelance journey. For every question I was asked in the Reddit post, I wrote a tweet. That is more than 20 different questions around the same topic. I am scheduling content around those questions, it will be enough for the first couple of months of 2024.

## Books

I published 2 books on Soccer Betting and coding in 2020. Probably one of the decisions with the best ROI of my entire life. Those books keep selling today, slowly but steadily. I have sold more than 200 copies this year and I have spent maybe 3 days of work on it in the entire 2023. What did I do? A couple of updates to the landing page, just to play around and see if the conversion improved. And, the most important thing, setting up a discount code for the weeks leading to Black Friday. More than half of my Gumroad sales happened in those 2 weeks when I promoted the book with a discount code on a few places online. I made more than $1500 in 2023 from selling books. It’s an average monthly salary in many European countries. It’s not much, but it proves that I can still make money online, on my terms, selling something I created. That’s a very motivating realization.

Am I satisfied with my accomplishments in 2023? If I told myself 5 years ago that I would be freelancing one day, he would be quite happy. Having done that for 6 months now, I am still happy, but I understand it’s not what I want to do for the rest of my life. This year I turned 40, I don’t have 10 years of high mental output in front of me to bootstrap an online business, so I cannot afford to spend a lot of time working on freelance contracts. Time spent that way is similar to employment, and the money you make depends only on the time you spend working. The time spent building a business is an investment, that has a chance to repay you 10x and sustain you and your family for a lifetime.

So, next year I will spend less time freelancing and more time trying to bootstrap a business. And I will try not to burn out in the process.