These last few months, I was in a bit of a pickle.

Not a physical pickle of course. Most pickles are too small for me to fit in there. Not that I actually tried it or anything... But we're talking about proverbial pickle here:

Compared to the small amount of traffic I get, this blog is making me a spectacular amount of money.

However, compared to the poverty line, my income falls way below that. I actually made more money from busking on Venice boardwalk when I was homeless than I do now.

Looking at the stats of this website, it’s clear that if I can get just 600 pageviews a day or something (pretty realistic goal if you ask me), and continue to provide as much value as I can to those people, I’ll be able to live off of this.

I’m truly confident that I can make this happen if I stick with it and work hard. On the other hand, right now I can barely afford food, and I often have to decline awesome invitations simply because I can’t afford to go. So not only does this proverbial pickle affect my own happiness,it affects the other people in my life as well.

I’ve always been a firm believer in following your heart/bliss/whatever your favorite fluff word is. But so far it hasn’t been the best strategy for me in terms of survival value.

I went to a couple of online message boards and asked for career advice, explaining:

“This blog is clearly something worth pursuing, and I will not give it up as my main career goal. But what I’m doing now is not working for me financially. So if there’s anyone here who has a succesful blog or passion project that they live off… What sort of advice can you give me?

Should I get a full-time job, save some money and return to working on the blog later?

Should I get a part-time job to support myself, even if that means significantly reducing the time I can work on it?

Should I stick it out and have a less fulfilling lifestyle for a while until it takes off?”

I got some helpful answers from the Reddit community (mostly ideas for semi-jobs that I can combine with blogging, thank you people! You’re amazing.) But in most places, I could divide the commentors in 2 categories. You may recognize them from your own life:

Category 1: The bitter people who gave up on their dreams.

“Jeez… Another loser musician and self-proclaimed blogger. Don’t make me laugh. Get a real career you dipshit.”

Category 2: The naive dreamers. 

“Don’t listen to those people in Category 1. They are just taking out their own misery on you. Never get a job. Jobs are evil. Just have faith, special snowflake. If you always do what’s in your heart, the universe will conspire to give you an abundance of everything you need.”

If you were reading between the lines, you may have noticed that in true internet fashion, 0% of that advice came from people who actually had any experience with turning their passion into an income.

Disappointed by these results, and knowing there were probably a lot more people like me or you who are tired of hearing the same fluffy advice from people who aren’t in a position to give it, I made a decision:

I said “Fuck it! Let’s be bold.” And started mailing people who actually did it successfully, so I could spread some of their real talk to other people in my position.

Here is what they had to tell you:


Wade Alters

Wade has been coaching men across the globe since 2007 in over 40 countries. He used to teach them how to meet women, but later shifted to helping people get out of the rat race and thrive in today’s money society.

A couple of years ago (when he was still known as RSDBrad), his views on what he calls “Lifestyle Development” had a major influence on me. I also remembered him mentioning somewhere that he used to live out of a suitcase, which is a sign of true dedication to me. So this man was definitely on my “wishlist” of people I wanted some practical advice from:

Pep: When you already knew what you were going to do with your life, but financially weren’t there yet… What did you do?

Wade: I focused on building skills that would help me for when I went out on my own. For me that was learning more and more about marketing. Continually writing sales copy. Writing new letters every week for products that didn’t even exist yet. And devouring every book on the topic.

Pep: Did you take a job to support yourself while giving up leisure time to work on your career?

Wade: Nope. I had a falling out with my previous employer so I jumped in the deep end. I feel as if starting a business is like having a child, you’re never ready.

Pep: Did you go all in even when it left you starving for a while?

Wade: Yep, there were times where I had to float the business on credit cards and eat ramen noodles. But it was all worth it in the end.

Pep: What practical advice would you give to people who are on the fence about whether to go for it or not?

Wade: Like I said, you can never truly be ready. Focus on building as many skills as you can, learn how to market yourself effectively, and realize saving money now and having an emergency fund is getting you closer to the goals even if it’s not directly building your business.

From there, entrepreneurship is all about taking the leap of faith, so you have to get used to taking that risk sooner or later! Jump in!

For more advice about how to take that risk and jump right in, have a look at Wade's official website:


Chris Guillebeau

Being a New York Times’ best-selling author who has traveled to every country in the world and runs a very succesful blog, Chris was one of the people I secretly hoped to receive some advice from, but who I deemed least likely to answer.

I was once again reminded by how inaccurate our brains are at making realistic predictions, when 15 minutes later he sent me some very down to earth advice that all the dreamers and bitter people failed to see:

I think you should follow your dreams and get a job. Then use your free time—we all have some of it—to write or build your side hustle or whatever it is you want to do.

Not everyone can give everything up, and there are also plenty of people who like their day jobs but also have hobbies or passions that they want to pursue.

So don't believe anyone who tells you to make a false choice, in other words.

With gratitude,


If you're one of those weird people that like to do their own thing and ignore what anyone else expects of them (don't worry, I'm right there with you in the weirdo group as well 😉 ), check out Chris' awesome website.

He also wrote a whole bunch of books that can help you further with the subject of this post, which you can find here:

Side Hustle:  From Idea to Income In 27 Days

The Art of Non-Conformity: Set Your Own Rules, Live the Life You Want and Change the World

Born for This: How to Find the Work You Were Meant to Do

The $100 Startup

The Happiness of Pursuit: Finding the Quest That Will Bring Purpose to Your Life



I first met Toomas about 5 years ago through a mutual friend, who wanted to start some kind of company with us. I had been doing a lot of personal development work in the previous years, but I had no clue “personal development” was actually a thing. It was just something that came naturally to me. I didn’t know there were books and blogs and a huge industry behind it.

Back then Toomas’ blog was the most popular personal growth blog in Belgium (where we both lived). It was also the first blog I ever read and I ended up liking it a lot. Little did I know I would be doing something similar some day.

Toomas is the creator of the app “HabitBull”, which is hands down the best habit tracking app out there. And I don’t say that because I know the guy.  I say it because I bought every single habit tracker out there and this was the only one I liked 😉 He must’ve done something right, because for the last few years he has been living the digital nomad lifestyle so many of us dream of, while living off his income from the app.

Enough reasons for me to ask him for advice as well 😉

Pep: When you already knew what you were going to do with your life, but financially weren’t there yet… What did you do?

Toomas: I'm still not entirely sure what to do with my life, but I do know I want to create things. I want to keep working around my broad interests such as AI, writing, products, startups, maths etc. When I just graduated, I didn’t have any money at all. I knew I didn’t want to go into consultancy or other typical jobs for engineers, so I tried to move in the direction of my interests on a shoestring budget. I worked on several small projects for about a year and then made the move to London where I started my own company.

Pep: Did you take a job to support yourself while giving up leisure time to work on your career?

Toomas: I was lucky in the sense that one of my first apps was semi-successful, which created a bit of income. This allowed me to pursue writing and other projects that wouldn’t immediately generate revenue. On top of that I also did some freelancing gigs, but I always tried to push for as much freedom as possible (no hourly rate but a fixed sum for work completed, remote work etc)

Pep: Did you go all in even when it left you starving for a while?

Toomas: Luckily I was never starving. I had a pretty solid backup plan, but the worst thing that could happen (living in a tent eating only oatmeal) is still not that bad, realising this makes me push harder and take a bit more risks than other people.

Pep: What practical advice would you give to people who are on the fence about whether to go for it or not?

Toomas: As long as you don’t have children or a family to support, I’d say take a risk. Life is short. Someone close to me once told me she chose the wrong profession and got stuck in it her entire career.  She regrets it. If you do have a family to support, do it as a side project until you can support yourself.

Toomas recently started a brand new blog, which already has some awesome stories on it.  You can check it out at


Jordan Peterson

"JP" as my friend likes to call him, is a Canadian clinical psychologist, cultural critic and professor of psychology at the University of Toronto. His main areas of study are the psychology of religious and ideological belief, and the assessment and improvement of personality and performance. I’ve recently seen him “blow up” (at least that’s what it looked like for me), when suddenly all of my friends started sending me these great videos from this man I had never heard of before. I’m currently following his “self-authoring” program as , which is a tool that helps you gain better understanding of your own past, present and future and derive important insights from it. It’s been very interesting so far.

Here’s the advice I got from one of his fantastic lectures:

“Whenever I talk to people who are creative, and you should listen to this because I know what I’m talking about. If you happen to be creative -you’re a songwriter, another kind of musician, or an artist, or any number of the other things you might be, find a way to make money. And then practice your craft on the side. Because you will starve to death otherwise. Now for some of you that won’t be true, but that’s a tiny minority. Your best bet is to find a job that will keep body and soul together and parse off some time so that you can pursue your creative career.”

You can check out more of JP's insightful lectures on his YouTube channel and website:


Donald Latumahina

Donald is the blogger behind, one of the top 100 blogs in the world about personal effectiveness and self-development (and believe you me, there’s a shit ton of those).

This was Donald’s advice for me, and by extension, for you as well 😉

I would make a side project and then grow it to a side business. Later, after the business takes off, I can decide whether or not to leave my day job. That's the case with me. My blog started as a side project in 2006 and eventually became my full-time job since 2009. I don't recommend going all-in because building a business is hard. It's better to let it grow as a side business first.

Best regards,


Sam Ryter

Sam is a young, charismatic blogger, coach and (w)ryter who sums up his message as “Think less, love more.” Which is something that definitely resonates with me and my own evolution as a person over the last 2 years. His writing is pretty spiritual in nature sometimes, but void of dogma and applicable to real life situations. Which is the kind of “spiritual” I personally dig the most. So another person who’s opinion seemed worth asking 🙂

Here’s the extensive message he sent me back:

Pep: When you already knew what you were going to do with your life, but financially weren't there yet… What did you do?

Sam: Actually, for me it was special. I didn't really know what to do with my life.
For me it was always just a feeling to start something. Back then I had no idea where it would end up for me. I call this 'following my guts'. Where you don't really know what you want, but you have a tendency an attraction towards something. I learned to trust and follow that tendency. And it was along the way, where I got more clarity of what I deeply wanted.

And I learned something so valuable for my life: To see the opportunities to create money by being in service.

This is something, I believe most people blind themselves from...

If I look at the bigger picture and if I would look at all the things that I'm going to do - I'm not financially there. But I don't have to be 'there' yet. Everything has its time. I have a more clear idea of where to go with my life, but I also know that it will change by time. As we evolve and experience we change, even some of values change. Again, I don't believe we have to be financially 'there' to just start something. In my case, I had some savings (from a previous job) on my bank account. But I would have started even without the savings.

Pep: Did you take a job to support yourself while giving up leisure time to work on your writing career?

Sam: For me it was a different story. In the beginning I found a mentor with whom I lived with for almost 6 months. By that time I rarely made any money, but I took this time as 'learning' period. Through having a mentor, I got also introduced to incredible other people. That opened up a lot of opportunities for me. After a while I got more secure in what I was doing. I had the right contacts. And I had the tools and knowledge to 'create money' and sustain myself.

From that place, I knew that I can create my own business.

Pep: Did you go all in even when it left you starving for a while?

This is how it goes as a solo entrepreneur. I still don't know exactly how it will turn out. But I have a sense of trust, that I didn't have in the past.

Now I would go all in, and at the same time, I also know that I wouldn't ever need to starve. Because I believe in what I do, and I know that there is always a way to create money by doing what we love if we are aware enough.

Pep: What practical advice would you give to people who are on the fence about whether to go for it or not?

Sam: Slow down first. Take a deep breath. Check in with yourself...

We usually know exactly what to do already. We are just often too occupied by the mind. Deep inside, we know what is true for us, and when the right moment is here. But we rarely listen. It's important to make this decision not from the fearful mind but from a grounded, slowed-down place.

What helped for me was the realisation that, if I follow this 'truth' within me and create from a place of love, I can't fail. I can only gain experiences. And I knew that those experiences will bring me much further personally than every 'degree' I could attain.

If you want to read more of Sam's passionate writing or just like to witness a website design that makes me jealous as fuck, definitely go visit


Putting It All Together

First of all I want to take a moment to thank all these people from taking the time to read and reply to my messages.  I can clearly tell they put a lot of effort in this, which is downright awesome.

The experience-based advice from each of these awesome peeps, seems to be divided as well. But without exception, it was a lot more nuanced than the black/white advice we always get from people who never actually went out and tried it.

Like so many things in life, I believe it ultimately comes down to what your favorite flavor of misery is in life.

Does the thought of sleeping on the floor and eating a shitty diet for a while not bother you that much? Then what are you waiting for? Go have an adventure!

Does that seem horrific to you, but do you think you can tolerate a couple of years at a job you’re not passionate about? Then the answer is once again obvious.

In the end, I definitely resonated with Sam’s last answer (listening to your own inner voice).

While writing this, I realized the irony of it all. I had known exactly what to do all along (find a part-time  job that doesn't kill my soul, while continuing to work hard on this project and my music after hours). I just wasn’t listening to that inner voice because I didn’t really like what it had to say.  Part of me wanted to stay a flying Peter Pan forever, so I tried to procrastinate by looking for advice from other people first.

If that sounds like you, I’ll like to refer back to a line from Chris's email:

Don’t fall into the trap of thinking you have to make a false choice.

It doesn’t have to be an "either/or" choice. It can also be a “yes, and..” and choice. It's not a popular opinion on blogs like this one, but there's no shame in having a job that isn't exactly what you want to do, so you can support yourself. It’s a matter of doing what you have to do to make those dreams come true.

For a while, your life may not look a lot like the life you dreamed up for yourself (yet 😉 ), but don’t let anyone lead you to believe that makes you a failure.

Never ever, should you give up on your dreams and join team "bitter old man".

But neither should you stand in te way of those same dreams, by staying on team "naive Peter Pan".

I've made my choice, and it will be a challenging one.  But I can't wait to see how this story will continue to unfold.

Now what will you do with your dreams?


Receive Pepijn's new articles by email.

While there's enough articles here to fill a couple of books and sell them, keeping them on this site where you can read them all for free would be much more awesome! And it's amazing people like you who make that possible. If you feel like these posts have helped improve your life, please consider making a donation.

Categories: Blog