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Confessions of a Freelancer: 5 Mistakes I Won't Repeatby@liorb
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Confessions of a Freelancer: 5 Mistakes I Won't Repeat

by Lior BarakJune 20th, 2024
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As he hits the big 4-0 and prepares to dive back into the freelance world, I can't help but chuckle at my younger self. With age comes wisdom - or in my case, a hilarious collection of "what not to do" stories. So, grab a coffee (or something stronger), and let me tell you the top five mistakes this old freelancer won't be repeating that are shaping his triumphant comeback tour.
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As I hit the big 4-0 and prepare to dive back into the freelance world, I can't help but chuckle at my younger self. Oh, the enthusiasm! The naivety! The sheer audacity to think I could do it all! But as they say, with age comes wisdom - or in my case, a hilarious collection of "what not to do" stories.


So, grab a coffee (or something stronger), and let me tell you the top five mistakes this old freelancer won't be repeating that are shaping my triumphant comeback tour. Shared with 7 TED talks that will inspire you to be a better freelancer.

Freelancing Fails That Made Me Smarter

The 'Yes Man' Syndrome: When Enthusiasm Outpaces Expertise

Picture this: a bright-eyed freelancer (yours truly) bouncing around like a caffeinated squirrel, shouting "Yes, I can!" to every request that came my way. Build a dashboard? Sure! Write a Python script? Absolutely! Audit your analytics. Why not!


Spoiler alert: It didn't always end well. There was that time I confidently agreed to create a "simple" python-based pipeline with APIs for a client, only to find myself three days later, surrounded by cheap Lidl coffee caps, questioning my life choices and Googling (No chatbots to be used back then) "How to explain to the client that their request is hard."


Lesson learned: Define your niche, know your strengths, and don't be afraid to say "no" to projects outside your wheelhouse. Your sanity (and your clients) will thank you.


Client Roulette: The Perils of Not Knowing Your Audience

Ever walked into a room thinking you're the guest of honor, only to realize you've crashed the wrong party? That's how I felt during a workshop I once conducted for a team that didn't want to be there. The enthusiasm level was somewhere between the "DMV (Department of Motor Vehicles) line" and "watching paint dry."


As I fumbled through my carefully prepared presentation, I could almost hear the collective eye-rolls. It was like trying to sell ice to Eskimos - if the Eskimos were penguins, and I was offering them sunscreen.


Lesson learned: Know your audience inside and out. Understanding your ideal client profile isn't just good business - it's the difference between being a welcome guest and an awkward party crasher.

The Middleman Muddle: When Good Intentions Lead to Bad Outcomes

In my quest to be the ultimate problem-solver, I once found myself playing a tech matchmaker. A client needed a specific tool implemented, and I knew just the person for the job! Or so I thought.


What followed was a comedy of errors that would make Shakespeare proud. Delayed timelines, miscommunication, and I found myself stuck in the middle of a tech tug-of-war, feeling like a bewildered spectator at a particularly intense ping-pong match. All that was missing was some popcorn and a referee's whistle if it didn’t have a direct impact on what I was expected to deliver.


Lesson learned: Stick to what you know best. Being helpful is great, but not at the cost of your project's success or your professional relationships.

The Freebie Trap: Compensating Dissatisfaction with More Work

There I was, facing a client who looked about as satisfied as a cat in a bathtub. My brilliant solution? "Hey, let me throw in some extra work for free!" It was like trying to fix a leaky boat by drilling more holes.


Before I knew it, I was juggling multiple projects, working overtime, and still not hitting the mark. It was the professional equivalent of digging myself into a hole and then deciding the best way out was to keep digging.


Lesson learned: Set clear expectations from the start. If something's not working, address it head-on rather than trying to bury it under a mountain of free work.

The Discount Dilemma: When Generosity Comes Back to Haunt You

In my early days, I handed out discounts like they were party favors. "You get a discount! And you get a discount! Discounts for everyone!" It felt great at the moment, but it came back to bite me harder than a caffeinated chihuahua.


You get a discount! And you get a discount! Discounts for everyone!

Case in point: A client I'd given a hefty discount to in their startup phase came back years later, expecting the same deal. Trying to explain why my rates had increased was about as comfortable as a root canal surgery without anesthesia.


Lesson learned: Your time and expertise have value. Price them accordingly, and stick to your guns. Your bank account (and your self-respect) will thank you.

Turning Mistakes Into Mastery: My Freelance Comeback Tour

As I prepare to take the freelance plunge full-time, those hard-learned lessons from past missteps will shape a smarter, more focused approach going forward. Gone will be the overeager yes-man, the mismatched client-freelancer pairings, the accidental middleman roles, the freebie traps, and the discount debacles.


From those failures, I've discovered my true calling - serving as a strategic data partner for early-stage and scaling mobile app companies, especially in e-commerce and gaming. No more scattered as a jack-of-all-trades, but a master of tailored, data-driven growth strategies for this industry, or as I want to call it, “Data Operation Partner”.


My future services will directly tackle common pain points I've witnessed. From conducting workshops to define clear goals and KPIs, to assessing ROI and maximizing data investments, to optimizing pipelines for reduced costs - it's all about empowering clients to leverage their data for strategic growth and operational excellence.


Many companies struggle with high data costs and transforming insights into smart decision-making. My customized, data-driven solutions will cut through that chaos. Comprehensive health checks to uncover opportunities. Collaborative sessions with key stakeholders like CEOs, CDOs, and product teams to ensure seamless integration and measurable impact.


While my niche will crystallize in mobile/e-commerce, I know my expertise can translate across industries like healthcare, finance, and retail - anywhere data insights drive sustainable growth and elevate the customer experience.


This freelance journey has been priceless in lessons learned. From over-committing to undervaluing my work, I now emerge with a sharpened skillset, clarified mission, and belief in providing exceptional value through strategic data partnership.


Here's to using past missteps as stepping stones toward freelance mastery. May we all find the humor in our freshman freelancing flubs while using them as fuel for future success. I can't wait to begin this new chapter!


I will finish with Simon Sinek and start with WHY, which I hope you all know because this is exactly what we freelancers need to focus on.

Avoid rookie freelance blunders - read my hard-earned wisdom and level up your freelance game! Any tips I have forgotten? What lessons have you learned during your career?