The system for creating an interesting and antifragile career for yourself

My goal is to create some leverage in my life. I tried to design a system with worst case scenario being a well paid consultant.

In this post, I make the case that striking out on your own before you’re ready might be an insurance for creating a meaningful and successful (whatever it means for you) career on your own terms.

To use Nassim Taleb’s “Barbell strategy”: Maximize upsides while limiting downside and creating an antifragile career.

You own your time (kind of) as you become a better consultant and ship often projects on the side. The cost of starting a project is really low and by doing it publicly and learning we leverage to find great consulting clients.

I can’t say that I thought about any of that last year. It was mostly out of desperation that I looked for clients to offer freelance services. I just didn’t see myself taking on a job after my business failed…

Was I ready? No

Did I have the experience? No

Did I have the credentials? Hell no

Would I still be playing the game without some support from family and friends? Again, no!

Am I biased? 100% yes!

Below, I’ll explain what I call a system for success. It is my plan and a reminder and I think it’s bulletproof.


You get paid to learn

You have the opportunity to solve problems for people/companies and be rewarded for that. But we live in a new economy and a critical element like digital marketing is essential for businesses.

How do you learn it?

You find a resource, “how to” video, copy, implement and iterate!

And all these really useful skills that you build, you can learn them for cheap or free just by being systematic, curious and by pitching someone that needs them to solve the problem.

And you get paid for that.

Now that I made my case that you can learn and be paid, let’s go a bit deeper with this idea. Let’s be strategic and plan to learn something hard and useful for your own business.

Pick a skill you could be reasonably good at in an industry you know something of or are interested in and you get paid to learn the skill and at the same time to do market research for yourself. Not a bad deal!

Sprint at your own speed

Being in a fast moving environment is amazing to learn. You can skip right ahead and sprint towards learning the 20% that bring you the 80% of pretty much any hards skills really fast.

And it is something you can double down on when you need to sell services by solving interesting and expensive problems in a continuously changing economy.

I’ll take my case, one year ago I didn’t know anything about marketing automation and by being ignorant of what I didn’t know, using the internet to find solutions to all my problems and implementing, I learned an extremely useful skill fast (I had free time).

The speed I could learn and implement is what makes self-employment really great for the right kind of person.

Learn core skills for success and life

Besides the technical knowledge that I presented above, if you want to future-proof yourself, you need to bet on the skills that are going to matter in the future.

The soft skills and the emotional labor!

Reading, writing well and effectively, persuading, selling, showing courage, taking the lead, being creative, all these skills matter a lot and the best system to learn them is to practice them every day without really thinking.

I see now that I’m so much more resourceful just because I have to find a solution to step up.

Ok, but what is the system?

Work in public

Now there is something that I clearly didn’t do enough off, working in public.

Writing what you do, sharing what you learn, testing ideas and failing, or succeeding but doing it so publicly.

You might not see much reaction or ego metrics (likes and shares) but then you’ll talk to people, and they will sometimes comment that they read it, or they will talk about you and refer you to someone to find a gig, and another, and another.

Working in public is magic!

I was telling a client a few weeks ago that every single time that I produced a piece of content - which by all direct measure was always a failure with no likes, shares, comments... - a lead came in the pipeline. Could be much later, but all my current clients are linked somehow to something that I produced.

Work for and with whom you want to connect

It might be hard to work for meaningful organizations. And also hard to meet interesting and like-minded people.

One big mistake I made is that I looked for business opportunities at the beginning without thinking if the opportunities were good for me.

I have no clue (probably not) if they were even good but they were clearly not for me.

But slowly, learning (again!), I managed to think about who I wanted to connect with, people who were welcoming my ideas.

You can find any group online or offline, just go in the space and start adding value (I struggle with that)...

Find something at the intersection of these three groups

Self-awareness is really important.

The goal is to build leverage and to do so, it would be great to use your own strengths.

I would go and ship content, start projects at the intersection of these three intersections:

  1. What are your strengths/unique advantages?Go with your natural or environmental strengths. You might have deep knowledge of an industry and the people of an industry, you might be great at precision and details (conversion rate optimization/AB Testing) or more of a system thinker/big picture kind of person. Go do things that are easy for you and hard for others.
  2. What do you enjoy?Strentghs are not enough, what do you enjoy and whom do you enjoy working with? Who would you like to know better, connect with and serve? What change do you want to bring?
  3. What are the opportunities in the market?It’s critical, in a B2B world we talk money. Understanding the business behind the project is really important. What business results are you bringing? And what are the opportunities right now (that match your strengths and your envies)?


After introspection, I saw that I liked working on systems. My brain loves them and I can geek out about them an unealthy amount of time.

I’m most definitely not a details kind of guy but I like the big picture. I have some understanding of local businesses and especially the local financial advising from my background and my environment. And mixing that plus what I learned in marketing and automation gave me insights.

Ship often

The plan is bigger than being a freelancer/consultant. You want to create leverage by productizing yourself. What I mean by that is that you want to create products, projects that don’t require your input. But you don’t know what exactly now. The solution is to ship often products, ideas, productize services. Create a body of work and get into the habit of launching publicly.


What should happen if you follow that plan?

  • You create a system for being paid to learn skills that will make you a better consultant, gives your more time and do paid market research for your own projects.
  • You create a brand and a reputation that will open opportunities.

Best case scenario, your launches pay off and you have a product business that doesn’t require your time.

Worst case scenario, you become a highly paid consultant with better leverage or you sidetrack your career in a great company doing a really cool job. While everybody tries to climb the traditionnal ladder, you sprinted your way on a sidetrack and enter from the backdoor.

That is my plan. I wrote this piece for myself, like every single essay that I put out there.

As a side story, I had a few opportunities to work in interesting projects or companies (that didn’t work out) that I would never have starting at the bottom of an agency. The first year without a track record, much success or connections, but doing things differently gave me more opportunities than anything before.

And now what?

Map out your own Venn Diagram and ask yourself these 3 questions:

  1. What are my unique strengths/advantages?
  2. What do I like/Whom do I want to serve?
  3. What expensive skills/problems does the market value today?