How to Make the Career Shift Into Workshopping

Becoming a facilitator is a great career booster. But how do you it? We caught up with Ben Dehant, who has transformed his career as an expert workshopper.

Here at AJ&Smart we’re BIG believers in the power of two things: workshops (duhh!) & what they can do for your career, and the power of self-learning. 

So when we heard about Benjamin Dehant, who has transformed his career and made the shift from the hospitality industry into being a self-taught workshop facilitator and designer, we knew we needed to catch up with him!

We get asked all the time how to make the career shift into facilitation, and who better to answer all your burning questions, than a Workshopper who has made the jump himself! Take it away, Ben! 

Hi, Ben! We were so excited and inspired to learn about your story, but for those who don’t know you–tell us a little about yourself, which professional background do you have, and how  did you get into workshopping in the first place? 

Ben: Before I started my career change two years ago, I changed lots of jobs, mostly in the hospitality industry: I worked at a coffee shop, as a manager in a restaurant, at a fast food place, etc. 

When I was 30, I decided to change my life and make a career shift into the online space. The transition wasn’t straightforward and took me some time.  In the beginning, I wanted to start drop shipping T-shirts, so I started learning graphic design on my own. I started from zero, but by putting in lots of hours and effort could get to a place where I was confident in my skills. 

However, this didn’t feel like a perfect fit, so I started transitioning into web design–I did some minor projects for free to get the practice in, and learned as much as I could. I didn't have a lot of funds to invest in courses or education, so I was learning from YouTube videos and absorbing all the knowledge I could get my hands on.

This is actually how I stumbled upon AJ&Smart’s YouTube channel and that prompted me to start learning more about workshops and facilitation. AJ&Smart’s YouTube videos opened my eyes to one fact: if I wanted to stand out in the highly competitive field of design and set myself apart from all the other designers who had more experience than I did, I needed to have a special skill that would differentiate me–like workshopping! 

If I wanted to stand out in the highly competitive field of design, I needed to have a special skill that would differentiate me–like workshopping! 

Benjamin Dehant


About the same time, I found Gary Vee, and at the time he was advising everyone who wanted to build a personal brand online to make use of LinkedIn. In spirit with what I learned from AJ&Smart videos– getting started is more important than being right– I decided to give it a try and see how it would go. 

The more I learned about design and workshops, the more I got interested in the area. My network of facilitators started expanding, and I connected with Robert Skrobe, who organizes The Global Virtual Design Sprint (GVDS). I Joined the GVDS last year to get some Design Sprint practice in, even though at the time, I had no idea what I was doing. I was working as a courier for Uber Eats, working in a restaurant, learning web design, and trying to fit in learning about the Design Sprint as well.

The GVDS was my first step into the workshopper world. After that I discovered the Lightning Decision Jam, and started learning more about how to run other types of workshops.

Then the pandemic hit, and I had to directly jump into remote workshopping, which actually played out in my favour. 

Mural board Ben designed for a remote ice breaker event with 300 attendees


That's a prime example of creating a blue ocean within the existing market! And it really does sound like you are an avid self-learner: You started learning so many things from scratch on your own. How did you manage to fit all that learning in while balancing the demands of your normal life? 

Ben: It was definitely chaotic in the beginning because I had to work to pay my bills, allocate enough time to learn and practice my new skills, and also live my normal life! 

The way I organized the learning processes is by allocating a couple of hours in the morning and the afternoon for learning every day. I also made sure to find practical applications for every new skill I was learning. I understood that only gaining theoretical knowledge wouldn’t be useful to me, so I committed to completing actual projects: mostly helping out friends for free, just to get the practice in.  

Not all of these projects were successful: for example, I didn't sell nearly anything for my drop shipping project. I had to power through a lot of failures, and it was hard. But these projects ultimately allowed me to get better at the skills I was learning. 


Is Workshopping your main career now, or are you still in the transition phase? 

Ben: I’m splitting my time between workshop and web design projects. Currently, I’m also working on an exciting challenge of helping a local government administration in France switch over to remote/hybrid work. 

I do have enough workshops and web design projects to live off of, so I don’t need to go back to my former jobs. This is a big achievement for me!


Do you have any tips or advice for people who might also be thinking about a career change and are battling the uncertainty and the imposter syndrome?

Ben: Personally, I really wanted to change my life and I  knew I had to be serious about this if I wanted the change to happen. Plus, I kept thinking long-term and counted all the small wins that were accumulating over the months: landing one client, receiving good feedback after a workshop, etc. 

Counting all these small wins instead of focussing on the failures really helped me to stay consistent and keep pushing through.  

I saw the first big results after I have taken part in the Global Virtual Design Sprint. The participation fee was about 150 dollars at the time, and it was my first investment in education. More than that, it was a sign to myself that I take this endeavour seriously, that there’s some skin in the game, and I have to commit to this fully. 

Counting the small wins instead of focussing on the failures really helped me to stay consistent and keep pushing through.  

Benjamin Dehant

So for people trying to make the shift I'd definitely recommend setting the goals, but taking them step by step. Don't try to achieve everything at once! Break your project into smaller milestones and prioritize consistency over quick wins.

Learn how to design your own custom workshops

It took me several months to start seeing the results of my efforts. But instead of pouring over the fact that I had no clients, I changed the way I thought about ‘success’: showing up and doing the work was already a success, even if I didn't land a client or a contract.

Find your true motivation that will keep you going day after day, and create accountability by investing in yourself.

I changed the way I thought about ‘success’: showing up and doing the work was already a success, even if I didn't land a client or a contract.

Benjamin Dehant

What also helped me is finding and connecting with people who were in a similar situation with me: people who were also trying to make the career shift. 

Mural template Ben created for a meet up about Design Thinking in Japan, celebrating the cherry blossoms


You mentioned that LinkedIn was essential in getting first clients for you. How did you leverage your network and how did your client acquisition process look like?

Ben: In the beginning, there was no real strategy behind my LinkedIn presence, I was just trying to post at least once a week. That was realistic for me at the time, and I knew I could consistently do that.

Similarly to going the workshop route to differentiate myself, I consciously decided not to start an Instagram channel because the medium is over-saturated with talented designers and it’s harder to stand out and grow organically. I realized that with my resources at the time, I couldn't compete on Instagram. So I decided to go full in on LinkedIn. 

I had no more than 50 connections when I first started, and now I have around 4 thousand. This didn't happen overnight, I tried a lot of different tactics and made a lot of mistakes along the way. It took me a good while to refine my profile. 

The strategy that worked for me was to stay consistent despite lack of initial engagement, telling my story authentically, and making content that really helps other people. I never tried to straight-out sell anything, and focussed on delivering value first. 


How long did it take you to see the first results from your LinkedIn presence? 

Ben: I started around December 2019 , and it took me around 4 months to start getting the first requests. I did a ton of work for free at first to get in the practice in and solidify the learnings. After 8 months though, I started getting enough paid gigs.


As we were scheduling this interview, you mentioned you recently ran a workshop for a big pharmaceutical company. These types of companies are well known for being meticulous about selecting freelancers and companies they work with. How did you land that gig? 

Ben: Through a connection on LinkedIn!  The company was in a hurry to find a facilitator who could help them transfer their in-person meeting into a remote space, just before a lockdown. The offer was very short-notice, but I was flexible with my schedule and decided to apply. 

I think the reason I landed this client is that I didn’t ponder it too much. I guess I was one of the few facilitators who took on the challenge of preparing a workshop on such short notice. But I went with a tried and tested LDJ recipe and it worked out, even though I was quite nervous before the start of the workshop. In the end, if you have a recipe that works, you can rely on it. 


A career change is always nerve-wracking and exciting! For some professionals, switching to workshopping might seem natural (for example UX Designers, who end up facilitating a lot in the course of their careers.) But you switched from a completely different background. Which skills from your previous experience did you leverage to have a competitive edge in marketing yourself? 

Ben: I used to work as a restaurant manager, and having some managing experience definitely helped me with facilitation. As a manager, I trained people, and needed to be an active listener–all these skills came in useful as I started to facilitate.  

I think regardless of which field you come from, there are probabaly skills you can make use of in facilitation!

Any advice you want to give novice Workshoppers who are just starting out in this field? 

Ben: Everyone learns and develops differently, so find a system that works for you! 

Find real projects to work on, even if it's for free. And find a way for you to enjoy the learning curve and the process, otherwise you will not commit for long enough to see the outcomes. 


Learn more about Ben and his work over on his LinkedIn page, and check out the Mural boards that he’s creating! We dare you not to be inspired!


Anastasia Ushakova

Brand Strategist, Digital Marketer, and a Workshopper.