Risk Management for Freelancers Workshop

Risk Management for Freelancers Workshop

Eliminating risks and creating opportunities for a happy and stress-free working life

When we say we’re freelancers, people usually have two kinds of reactions: either they envy us, or they feel sorry for us.

The former sees us like incautious adventurers ready for any type of risk, pyrates facing all types of bad weather life can throw at us. The latter believe we’ll be miserable in the old age since we’re living without the paternal protection of a company.
What they don’t know is that a freelancer can eliminate the classic risks connected to this type of work and, in turn, s/he can transform a thousand threats in a thousand opportunities!

In this online workshop, “Risk Management for Freelancers” with Jacopo Romei, we’ll be putting the concept of risk within a rational framework, we’ll understand the effects this concept has on freelancers (even the emotional one), and we’ll learn how to face it and, even better, how to eliminate it!

Target Audience

  • Freelancers who end up being involved in ugly projects too often
  • Professionals who sell their services based on time units: per hour, per day, etc.
  • Freelancers who spend too much time with one client only
  • Employees who would like to go solo and they’re afraid to lose their guarantees
  • Independent professionals who find it difficult to liaise with other professionals
  • Freelancers who don’t know if a partner will be worth the money invested.


  • Tools to weight the merit in each collaboration
  • Techniques for money allocation upon the completion of a job
  • Negotiating agreements based on the job and not on the effort
  • Real cases of negotiation
  • Antifragility and risk in the transition towards a new career as freelancer
  • The role of demand and conversion rate in the career of a freelancer
  • Myths to dispel and suggestions about welfare for freelancers.


During this workshop with Jacopo, we’ll explore some techniques to reduce the most common risks of freelance work, as well as some real examples from Jacopo’s experience, with the aim of learning how to work stress-free and earn more.

We’ll try to understand the underlying principles of some operational decisions in order to be able to translate these decisions into the specific context of each professional. This way we’ll find some solutions that can work for everyone, and not ready-to-go recipes.

Each topic will have the same objective: being able to work stress-free at last and therefore to work with more satisfaction.


We’ll aim at covering as many topics as possible throughout the two modules, and we’ll do so by taking a generalist approach that can suit different types of freelancers with different skill sets.

Practical activities and simulations will be predominant, whilst slides and presentations will be kept at a minimum.

First session

  • Extreme Contracts and value-oriented contracts
  • Evaluation of the merits and recognition of the merit in each collaboration.

Second session

  • Antifragile business and elements of fragility in the knowledge work.

Learning Objectives

Here’s the 5 key takeaways of this workshop:

  • Negotiating agreements with the clients based on the value and not on the effort
  • Negotiating agreements with the partners based on the value and not on the effort
  • Being able to switch from “employee” to “self-employed” without this necessarily being a jump into the void
  • Understanding and rationalising the concept of risk despite the cognitive distortions typical of the human’s way of reasoning
  • Acknowledging the value of emotions as a starting point to identify the hypothesis of risk.

Why you shouldn’t miss it

At the end of the workshop, you’ll be able to work autonomously on new projects by taking the responsibility (and the benefit) to learn from your errors as much as you can.

The freelancers who join the workshop will be able to say that their work is of the most robust types around, and they’ll be able to work at their own pace without having to face the risks deriving from the relationship with the client, all of this without the paternal protection of your company.

Online Workshop – How does it work

The workshop will happen online and in live streaming: the trainer and all other participants will be in a video conference. You’ll be interacting and working together in real-time thanks to a variety of tools you’ll have at your disposal.

The workshop will keep its highly interactive and hands-on spirit despite being online.
This is why we require that all participants keep their webcam on for the whole duration of the workshop: this will enhance the quality of the communication and of the workshop as a whole.
You won’t be sitting at your desk watching slides and videos, and you’ll be engaged in real-time activities for the majority of the time… as if we were in a real classroom!

We’ll also explore some more theoretical concepts and ideas, but no prior university-level background is required.

The online workshop is based on some principles of the Training from the Back of the Room method, meaning that practical activities will be more predominant than lectures and presentations.
There will be a few moments of theory and a lot of exercises and practical activities.
The learning path will be completed by the interactions with other participants and the trainer’s support.


Is this a workshop for beginners or experts?
This workshop is aimed at any type of freelancers, or those willing to become one. No specific previous knowledge is required.

Do I need any previous knowledge in order to join the workshop? Are there any recommended reads?
The workshop is accessible to anyone, however we do recommend you read the following before you enroll:

Is there anything I must do before I buy a ticket for this online workshop?
If you have a computer/tablet, a stable connection (at least 20 Mbps in download and 10 Mbps in upload), earphones, a microphone, and a webcam, then you’re ready to join the workshop.
You’ll get detailed information on what tools we’ll be using and how to get ready a couple of weeks prior to the workshop.
Check out your connection’s speed.
The workshop will keep its highly interactive and hands-on spirit despite being online. This is why we require that all participants keep their webcam on for the whole duration of the workshop: this will enhance the quality of the communication and of the workshop as a whole.


This workshop will be confirmed upon reaching the minimum number of participants. We’ll send an official confirmation to all registered attendees two weeks prior to the workshop dates at the latest.

Practical Info

Language: English
Max number of participants: 25 participants
Tools and Workstation: The workshop will take place online and in live streaming by using digital tools. You’ll get detailed information on how to join the online workshop, how to get ready for it, and how it will work a couple of weeks prior to the workshop.


If you’re not able to give the right value to your work, to yourself and to your material needs… this workshop will change the way you see things altogether!Veronica Giaché

I’ve changed the way I consider my own time. Spoiler: I’m not selling my goods anymore, but the benefits my goods provide.Nicola Stocco – Business Partner

Selling your own time is the most natural thing to do if you’re a freelancer. But Jacopo taught us to offer our value instead. There’s no turning back!Davide Corio – Solutions Architect

A workshop that will teach you how being a (social media ads expert) freelancer is not necessarily an extreme and reckless choice. Quite the opposite: by taking advantage of the spaces that open up between – more or less monolithic – companies is actually the most rational thing one can do. It will help you be ready for all the good that might happen professionally.Matteo Figoli – Web Marketing Strategist

For the first time since I left my previous company (as an employee), I’ve started to see the glass half full!Agnese Iannone – SAP Functional Analyst

An experience that will help you dissipate all clichés about working as a freelancer. You’ll understand that your potential is really big and you can actually create your work the way you like it!Barbara Robiolio Bose – Senior .NET Developer

The “Risk Management for Freelancers” workshop is a great starting point if you’re starting as a freelancer. After this day spent with Jacopo, I’m more confident than before about my choice (of going solo) and the value I want to generate with my work.Alice Luidelli – Freelancer Graphic Designer

Jacopo Romei

Consultant, entrepreneur, trainer, Jacopo works with teams across Italy, France & UK.

Usually, Jacopo gets hired by those willing to waste less time, money and happiness and he helps people working in teams to work better because our jobs are a significant part of our lives.

In 2003 he uncovered better, agile, ways of developing software while he was starting his first company up, at just 23. His third company, ideato, contributed in establishing an Italian Agile Community and keeps on nowadays.




In February 2018, Avanscoperta sponsored Jacopo to fly to New York to take part in a 5-day workshop titled “Real World Risk” led by Nassim N. Taleb and he recorded his impressions on our blog! Read the full story

About us

Avanscoperta is a growing community of professionals learning together, exchanging experiences and ideas, exploring uncharted territories.

We carefully select the most relevant topics and the best trainers and thought leaders worldwide with an eye to the most engaging teaching techniques.
Are you ready to learn with us? ?

Are you interested in this course?

If you have any specific questions, or if you want to receive more information on dates, content or offers about this course, drop us a line. We'll gladly get back to you!


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