I’m offering free career and financial education coaching in Q1 2020!

Hi dear reader, haven’t you dreamed about being RIP’s guinea pig all the time?

Today is the day your dreams become true!

RIP, what the hell are you talking about?

I’ve spent a good portion of 2019 talking with people, helping people and – more importantly – getting help fromย  people. I loved that. I want to keep doing this. I want to do more of it!

But I’m not an expert in anything. I am a jerk of all trades. Master of none. The more I learn, the more I know I don’t know. That’s why I keep learning.

Using Blas Moros‘ words (in his review of Venkatesh Rao’s The Gervais Principle):

Literacy of any sort gives you the power to recognize and unambiguously label things that the illiterate can easily ignore as noise, fads and bullshit

While knowing that I don’t know, I’m also getting better at finding patterns, blind spots, connecting the dots, asking the right questions…

RIP, wake me up when you’re done with your bullshits, ok?

Wake up bro, here we go!

I want to launch this medium-level commitment experiment: I’m going to offer a free career and personal finance coaching experience to up to 6 people in January-March 2020 ๐Ÿ™‚

Apply now! ๐Ÿ˜€

Meet your enlightened coach

Wait… RIP, are you qualified for this?

Of course I’m not… Or am I?

I pursued and reached my dream jobs. Yes, ok, then they failed to meet my expectations, but that’s another bag of experience points I can add to the table.

I have a kind of objectively successful career, working in one of the most relevant companies in the world. I know what skills are on demand and how to think like a 10x Software Engineer. Yes, ok, a career that has not been all roses (and maybe more thorns than roses), but which one is not?

I was able to increase my earnings, control my spending, invest the difference keeping financial emotions at bay (so far), up to the point of being your millionaire next door. Yes, ok, I made shitty mistakes investing in 2000-2002 and buying a crappy flat in 2010 instead of dropping the money into a S&P500 ETF, but let’s learn together from my mistakes!

I think I can help you. Or you can help me ๐Ÿ˜€

But of course I’m not an expert in coaching, that’s why I’m doing my “internship” at Y.O.U. inc. ๐Ÿ™‚

RIP, why are you doing this?

Because if I have to list the deepest moments of last couple of years that don’t involve my family and small circle of friends I would mention all the deep interactions I had with my readers and the people I met thanks to my blog.

I got a lot of help, ideas, stimuli. I gave something back, but I want to get better at it.

And I know this is something I might want to keep doing in my future, post-Hooli career.

Not convinced. First: is it really free? Free as in free beer?

Yes, free! Gratis! Kostenlos! Gratuit!

I know that someone would insist in paying me back somehow. You don’t have to. I’m doing my internship, you’re my first assignment. I’m learning a new skill, you’re my beta tester.

But if you really insist, feel free to donate any amount on my paypal.me blog account:


Since few people asked how can they donate me some money, feel free to use the same link.

Let’s say I’m interested, what should I expect to get out of this coaching thing?

It’s up to you!

I can help you sharpening your skills.

I can help you evaluating your current career, planning next steps.

I can offer you my experience with fighting burnout, that might help you detecting and preventing it.

I can help you achieving financial awareness. Do you know how much you spend? Do you know how much you have?

I can help you achieving financial intelligence. Let’s prioritize your financial goals! Let’s grow your income! Let’s review your expenses! Let’s make a budget! Let’s invest! Let’s plan your (early?) retirement!

I can help you achieving financial independence, let’s dream big!

I can keep yourself accountable in all of the above.

If you’re following me you probably have an opinion about what I’m good at. Leverage that.

… And you don’t ask anything in exchange for this?

That’s the magic of being in such a financially solid position. I have the luxury of thinking very long term! I’m designing my ideal life and making steps toward it. That’s one small step for Mr RIP, one giant leap for mankind. I can afford to “work for free”, because as MMM says: “work is better when you don’t need the money

Of course it’s not guaranteed that future editions will still be free. This might go nowhere, or become my barista FIRE strategy. Who knows!

Since I want to learn more and get good at it (which means I can’t guarantee good quality and results), I’m focusing on a small number of participants for now: I will accept no more than 5 or 6 cases.

But I lied.

I’ll ask you something in return for this!

Here we go! Scaaaaaam!

Yeah, I was cheating ๐Ÿ™‚

First, I’m more likely to accept the most interesting cases. If you want to apply to this free coaching cycle, you need to market your case well and convince me that I desperately want to help you more than the others.

Second, I prefer transparency and openness. You can look at my numbers, they’re out in the wild. From you, I would like the same level of transparency with me. I want to be able to talk about raw numbers, not abstract concepts.

Third, I demand your same level of commitment that I’ll put in this project, and something more. If we schedule a call, be there. If we decide you’re going to track your expenses and report them in a month, do it.

Fourth, I’m here to learn. I will ask for feedback, be harsh. Don’t be afraid of telling me what was useful and what was useless. I’m not taking anything personal, but try to transform a “you suck!” into a “you suck because X, Y, and Z. I was expecting A, B, and C!”

Fifth, I’d like to have some freedom to document this experience here in the blog. Of course with as much obfuscation and anonymization as you desire, but I’d like to be able to talk about my experience with you. Bonus points (not a requirement though) if you are willing to be a “reader case” and would let me blog openly (but anonymously) about your issue.

Ok, let’s say I applied and you chose me. What happens next? How do you intend to do your coaching sessions? What is the timeline?

Too many questions! Let’s start from the timeline.

I’d like to have the slots filed by mid December. Ideally you should apply before end of November, since few back-and-forth might be required on my side to gather more information.

In case you’re selected, I’ll let you know.

If you don’t receive a reply it’s probably not because I’m acting rude, but because something higher priority took control. Or maybe it’s because I received an overwhelming number of applications.

Ok, you’ve been selected. Congratulations (and thank you)!

Now what?

We’d “meet” (either physically or digitally) 3-4 times over the course of the experiment. I’d say early January, early February, early March and end of March, but this is not set in stone. I expect each session to last no more than 1 hour.

We’d also exchange emails when needed and/or setup other async communication channels. I’ll ask you updates, progresses, reports and so on. Don’t expect me to be ultra responsive. A latency of up to 1-2 days should be tolerated. This should also be true on your side.

At the end of the experiment you’ll give me feedback. I may prepare a form, but more likely I won’t. Prepare to give me free form feedback, and tell me what I did good and what I could improve.

Then we’re done.

Goodbye. See you. Auf wiedersehen. Au revoir. Ciao ciao!

But RIP, we just created a connection… I thought we were friend ๐Ÿ™ seduced and abandoned…

No, wait, don’t cry ๐Ÿ™

Of course I’ll get attached to your case! Our relationship won’t end on March 31st. If we have some plan that needs to be executed, some deadline that needs to be met, some condition that needs to be waited for… I will want to know what happened! Feel free to send me updates and keep the channel open! Just be prepared to receive a “best effort” kind of support ๐Ÿ™‚

Holy shit, I now speak like a Reliability Engineer…

I’m in! How do I apply?


Send me an email to retireinprogress+coaching (at) gmail (dot) com

In the body of the email:

  • Introduce yourself (age range, family status, location(s), current career, financial situation).
  • tell me what are your current challenges.
  • tell me what you would like to focus on during our experiment.
  • tell me I’m awesome convince me that I want to work on your case.

Think of me as a “human venture capitalist”, and make your pitch for my attention in a single email. Not extremely long (who am I to tell you otherwise?), with few external links (but I’d love to see links to your spreadsheets/docs).

I’ll take the most interesting cases! I’d like diversity, challenges, fun! Tell me why I should be interested in mentoring you for free.

That’s it.

But RIP, you don’t have time to brush your teeth and you think you’re going to keep up with this?

I know, but this is something that I value a lot.

I’m already doing something similar, just less structured.

I will make time ๐Ÿ™‚


UPDATE #1: Friday Nov 8th, 11.30am, two hours have not yet passed since I posted this, and I already got 6 applicants… wow ๐Ÿ˜ฎ there will be some competition!

UPDATE #2: Friday Nov 8th, 8.30pm, first day is not over yet, and I received more than 20 applications! I’m honored, I’ll try to reply to you all in the following days. That doesn’t mean applications are closed, but… just to tell you the odds ๐Ÿ™‚

UPDATE $3: Sunday Nov 10th, 2pm, I wrote a follow-up post. Please take a look.


  1. Super regretted not have discovered Mr.RIP earlier and missed that opportunity. I would have, for sure, applied to that coaching!! Is there any possibilities that you are gonna do it again? Or do it by paying a fee?

    1. At the moment I don’t have enough time for it.
      Probably I’m going to offer coaching (not free anymore) if/when I’ll quit my old career for good ๐Ÿ™‚

      1. Makes sense! Thank you for your response. I’ll wait for that ๐Ÿ˜€
        In the meantime I want to try asking for a whereby.com evening friendly call, if you can/want.

  2. Ciao!! Mi chiamo Christian ed anche io sono un romano di Roma che vive a Zurigo da circa cinque anni. Gestisco due negozi italiani ( al 100% italiani eh ).
    Mi farebbe piacere un giorno scambiare due chiacchiere, davanti a cappuccio e cornetto ๐Ÿ™‚
    Complimenti per il blog

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