9 Scary Questions to Ask Before Setting Off to the Land of Solopreneurship

Written by Conni Biesalski. Follow me on Twitter and Google+.

I’ve freestyled life since I was 15, and in the most truest sense since starting my full-time vagabond life in July 2009.

However, the change that is coming on is different.

The decisions I am making are different. I’m about to fly solo.

I have promised to leave this anti-sabbatical business behind. No more working shitty jobs in exchange for travel funds.

I quit my current anti-sabbatical job in PR a few weeks ago; my last day is on January 31st 2012. That’s about six weeks away, of which about two I’m on vacation. So four weeks left of working for someone else. (Still too long.)

In the meantime, I'm left hanging in mid-air.

Like in my dream I had the other day: I was on a plane and the plane started accelerating on the runway, it kept on accelerating and going and going and going…but it never took off! This reflects prett well how I'm feeling these days.


My Personal Revolution

Soon, I am starting a new era in my life. An era where I will live my passions and dreams 24/7 without any more compromises.

This is going to be my personal declaration of independence.

I’m on the way to become a solopreneur and freelancer, a terrain that is quite unfamiliar to me. The map I’m looking at still has a lot of black spots.

So having made my public promise a few weeks back, I thought it would be a good idea to write about

  • the questions I've been asking myself – wondering and worrying about. They are questions I would advice anyone who is planning on flying solo to consider. Answering them will make everything a bit clearer.

  • let you know how I’m dealing with the current situation of having quit my job and finding myself a bit in limbo.


So here we go:

My ten questions. Recommended exercise for any aspiring solopreneur or freelancer.


1. What the fuck am I doing?

Does this make sense? Are all these people who are ‘making’ it online and in the blogosphere really real and not just faking to be making it? Do I have the same success-genes as them?

I can really only believe in myself and my projects because of all these amazing and inspiring people out there in the blogosphere, who are doing it, rocking it and helping others do and rock it too (let’s just think Chris Guillebeau, Jonathan Mead and many more).

If I was to depend on my personal life in the touchy world (as I like to call it), then I would have probably given up a long time ago. I might not have gotten the idea in the first place. Actually, I think I would have called myself stupid and unrealistic if I had – which would make me highly conventional and normal.

I am also fortunate to have a mum and a partner who both believe in me and my plans and any crazy idea or dream I happen to follow. It’s important to have at least one anchor in the touchy world that gives you feedback and support. Which is why you read so much about “surrounding yourself with the right people”. I totally get that now. Because if not, if you are a one-man/woman island, you might not pull through. The rest will pull you over to the realistic side and you will realise that everything was just a dumb idea after all and then forget about it. How sad would that be? I can’t even think about it.


2. Can I handle the business side of being a solopreneur?

How much do I actually know about business? To be honest, not very much.

I never thought I would be going down this road. Rather despised everything business and corporate and capitalist. I seriously never considered becoming an entrepreneur. Never. Insane actually, thinking about that now.

I’m trying my best to catch up on business knowledge (rewards link), reading and reading everything I can get my hands on from business principles to (online) marketing and being a entrepreneur and freelancer.

It’s fun and I’m enjoying the learning process, but I won’t be overdoing it. I don’t want to build a Fortune 500 money-making slaughterhouse, just my little one-woman show.


3. Do I have the discipline?

The keyword here is the big P-word that ends with rocrastination.

I know I have a mountain of motivation and enthusiasm, and I know I was disciplined enough at uni to write a bloody massive 300-page grade-A Master’s thesis on my couch while going out drinking four times a week.

So yes, I believe I can do this.

Can I be sure? Fuck no. I’m gonna have to find out.

If anything, I’ve go Steven Pressfield's The War of Art to fall back on. His words always manage to kick my ass back on the working treadmill. My own personal passion treadmill I love running on by the way. Makes it easier to be disciplined.

I’m disciplined enough to work a full-time job and start and run a blog after-hours, for which I publish at least twice a week. Apart from that I'm pre-planning my solopreneur life. I’m already working long hours every day. And I love it, cause I love what I’m doing.


4. Can I handle the paperwork and legal stuff?

I’m gonna have to, won’t I? With a little help from my friends I can pull this MoFo off too.

The plan is to deal with it as it comes up. Gladly I have a few people in my social networks who I’m sure can give me some advice. If not, I’ll just read some more books and blogs, right?


5. Is this going to stress me out?

Life-work balance comes to mind. And you know what? This concept makes me want to vomit.

I’m not gonna have a life-work balance, because I will have a 100% life-life. That’s what I’m doing this for. The moment it starts to stress me out is the moment I have to quit this all and claim unemployment or social benefits, man. Seriously.

Life-work balance is a lot of BS in my world. What a sad world is this anyway where a concept like this even exists.

I won’t do more work and take on more clients than I can handle period. And since I don’t need much to live and since I won’t be living in Western countries, I won’t need to work my ass of. Easy.

Apart from that, there is always Yoga.


6. Can I organise myself well enough?

I’m a massive organiser actually. I’m German duh!

At the moment I’m already in the process of structuring my tasks and strategising my plans.

Since I feel overwhelmed really easily, I have to be very organised, as otherwise I get paralysed and start procrastinating heavily.


7. Can I actually make money? In the long run too?

I certainly hope so! But with all my skills and product ideas I have up my sleeve, seriously, how could I not? I'm pretty confident on this one. Not that this is always easy, but it's all I have sometimes.

Of course these questions worry me, but that’s just my inner critic trying to pull me down.


8. Do I have a backup plan?

What if I run out of money before my plan becomes profitable? Definitely a thought to consider, ey!

I’m actually a tiny bit prepared (comes with the German organisation package).

I have a couple of small safety nets which I'm confidently relying on:

  1. I’m a scuba dive instructor and can always find a full-time job or freelance (planned option while running my business) doing that. It’s work in paradise doing what I love, so that’s cool. I don’t think I would ever want to give this up completely anyway. I love being underwater and teaching others to do it as well.
  2. I will be helping my mum and her small business out a bit, as a relaunch is planned early/mid 2012. She wants me to do the PR and Social Media side of it, so that’s some safe money in the bank right there.
  3. I will have a bit of money saved up by the time I start flying solo and leave Germany. It’s not a whole lot (~ 4000 Euros), but because of #1 and #2 above, it doesn’t have to be.


9. What is my plan really?

You’ve probably been wondering about that for a while now.

I plan to have several different income streams, which don't have to be all running at the same time, but possibly could.

So here it is, this is how I intend to make a living:

  • Freelance PR Consulting & Social Media Management. For anyone who is interested (my mum being my first official client, yeah) – I will be advertising my services on connibiesalski.com and mention it on this blog as well (but not prominently)
  • Freelance Scuba Dive Instructor. Off to Indonesia end of April 2012, back to the island where I lived and worked before (Gili Trawangan, Lombok). High season starts June-ish (till September-ish), which gives me the confidence that there will be plenty of freelance work available and thus money to be made.
  • Write (e-)book(s) and/or a paid subscription letter for A Life of Blue readers. Writing is becoming a bigger and bigger part of my life (again), and with the million ideas in my head it would be a waste to leave them to rot away. I want to be of help to my readers and anyone else who is interested and provide them with the greatest value possible.
  • Other possible income streams: freelance (article/blog) writing, wordpress blog setup, translations, travel consulting…


And then I step away.

I think: Screw this, screw all the doubts and worries. Shut up you useless inner critic.

How will I be able to answer any of these questions without going for it?

I’m gonna jump no matter what the answers to all these questions are.

I call this the FYF Principle.

FYF = Fuck Your Fears = Do something no matter what. Hold your breath and jump. Jump despite not knowing where you will land.

I know what I want and I’m gonna go and get it. FYF!!!!!



And if the fears come back, I go and watch Jon Jandai's crazy inspirational TEDxTalk:



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28 Responses to 9 Scary Questions to Ask Before Setting Off to the Land of Solopreneurship

  1. Tom Ewer says:

    Hell yeah! All of the above ;)
    Seriously though, you know I'm in the same boat, and I've run through the same list myself. The easiest way I found to justify my move was this: "I may not know what I want, but I do know what I don't want. And I'm going to start this journey by moving away from that." That way of thinking made the decision really easy for me.

    • Conni says:

      True that, Tom!

      The frustration about what I don’t want makes it so much easier to jump. Because I’d rather die tomorrow than living a life I don’t enjoy, doing things I despise and dreading getting up in the morning.

  2. Dan says:

    Sounds like a great plan Conni! I'm sure you'll make it happen.
    That's a great video too, thanks for sharing!

    • Conni says:

      Cheers, Dan! I’m pretty impressed with myself, having lived most of my life plan-less (sort of knowing what I want but no idea how to get there exactly) – having discovered other people in the blogosphere made it ‘click’ massively!

      All the best to you too! Let’s be believers, shall we!

  3. Lately i find more and more people thinking like me, which is very encouraging. I have been stuck in this here country for way to long and articles like yours, knowing there are others like me, keep me going at working towards the point when i can leave again. Leaving the fake behind, embracing the real. Thanks, Conni.
    "It's better to live your own destiny imperfectly than to live an imitation of somebody else's life with perfection."

    • Conni says:

      I know how you feel.. I thought I was by myself with my beliefs until…yes until I found others who shared them with me.

      I like how you put it: ‘Leaving the fake behind, embracing the real.’ – That’s exactly what it feels like.

      All the best, go for it!!!

  4. Raam Dev says:

    It's fantastic to see you in the mist of so much movement. Clarity is a wonderful motivator! :)
    I'm in a similar transition — an unusual desire to cultivate entrepreneurship after being almost certain for the past year that I wanted nothing to do with business.
    What changed my mind was releasing myself from the status quo of business. I don't need to conduct, build, or create businesses "the way everybody else does it". I can create my own business models, my own value-based systems and methods. This realization — realizing that I could throw out all the rules and do everything the way I thought it should be done — inspired me beyond belief.
    So, when you're reading all those business books, I urge you to remember that if something doesn't make sense, you don't need to do it. :)
    Also, thanks for sharing that incredible TED talk. I already have a list of people in my head who I want to show it to.

    • Conni says:

      Aww Raam, as always, you’re speaking my heart! Thank you so much for your words, and thank you so much for doing and thinking about ‘business’ the way you do. You’re one of the good ones, the one I trust. 90% of all the business books I read make me so sceptical, you know. I guess I was exposed to Marxist and critical ideas for too long ;) For the most part, I feel like I need to know what’s out there, see how the conventional business/marketing system works in order to then screw it and adapt it to the way I see the world, my world. The only thing is that I would eventually like to make a living off of doing the things I love, but in a way that I don’t have to conform to the status quo of how capitalism works. I’m glad we share the same views, and thank you for serving as an inspiration.

  5. Noemi says:

    I love your bravery and authenticity, and no-bullshit attitude! I think I'm going to make "FYF" one of my favorite acronyms to use. I'm in the same boat as you and feel that it's not a bad idea to set off on your own in creating a life full of abundance away from the conventional (and boring) realms of this world. 
    Every day I'm learning that more and more people share the same views I do, and I'm happy I came across yours. I'm wishing you all the best of luck and hope that we can run in to each other in the future! 
    You are an inspiration Conni! Thanks for sharing your fearlessness!! :D

    • Conni says:

      Wow, thanks for your words, Noemi! I’m glad another free soul found my blog and shares my ideas and aspirations! I love it!

      You know, I thought about playing it nicely, this whole blogging thing, but when I write about things that really move me, that’s when my inner voice comes out. I just can’t hold back anymore..it feels like it’s been brewing for a long time, and I’m finally letting it out. Not the easiest thing to hit publish, but screw fears, right? ;)

      Let’s do this, Noemi! I’m glad to have you on boat!

  6. Srinivas says:

    This is easily one of the best things I've read all week. I love those questions. It makes feel  a little less like I"ve lost my damn mind considering I ask myself those questions on almost a daily basis. They're hard questions, but once we can answer them, things really open up to us., 

    • Conni says:

      What a compliment, Srini, I feel flattered ;) I did pour parts of my heart and soul into this post as it just had to come out so badly, it felt like I was overflowing with these thoughts. I’m glad they resonate with you, so good to hear I’m not alone with them :)

  7. Benny says:

    Conni that's wonderful! I can relate to many of your points. You definitely have a good plan laid out of how to earn income. I haven't been much of an entrepreneur till this year, and I've learned from listening to podcasts, reading magazines, reading books, reading blogs and wherever I can pick up advice. 
    I wish you best of luck on this new journey and look forward to following along here!

    • Conni says:

      Thank you so much for your lovely words! I’m so glad to be sharing this journey with you and so many other people who stopped by with words of encouragement, just wow! I love your blog by the way, really awesome content and inspiration!!

  8. Thank you Connie for your FYF Principal and post!  I'm Sam from Financial Samurai and the Yakezie Network and wanted to say hello.

    I will tell you this: Going solo is ENORMOUSLY difficult!  The paper work, taxes, legal, administration will suck your soul out as it is sucking my soul out at times right now.  The irony is, the bigger you get, the MORE work you will have, and yes, the more business too.   It gets ridiculous, and no matter how much money you start to make, you will STOP CARING and want your freedom and simplicity back.

    Going solo is liberating.  Just be prepared for some very rough times.  Best of luck and hope to see you around.

    Best, Sam

    • Conni says:

      Hi Sam,

      cheers for stopping by! Sounds a bit intimidating when you say it that way, plus coming from you, a financial pro.

      But I’m glad to get your perspective on it – at least I can’t say I wasn’t warned when the difficulties and the stress hit me after all! However, I will fight against anything that tries to suck my soul out with all I have and believe in. I just can’t let that happen ;)

      All the best to you, too!

    • Raam Dev says:

      Sam, I have to disagree.

      I think going solo is only enormously difficult if we choose to make it so. I believe there’s a huge misconception around what it takes to do and run a business. If we focus on using the business to assist *us* in our goals — as a vehicle for creating our own utopia, as Derek Sivers likes to say (sivers.org) — then our business, big or small, becomes a joy, not a soul-sucker.

      If our goals involve doing something that will require lots of paperwork, taxes, administration, etc., and we feel those things will “suck away our soul”, then we should be prepared to delegate those tasks to people who have made it their business to take care of them.

      An increase in work should be an increase in *fun*. If our business is actually creating our own utopia — actually creating a playground, an environment where our passions and dreams can thrive — then more work won’t cause us to stop caring. It won’t suck our soul.

      I believe the focus of business should *not* be on money (as that often leads to soul-sucking stuff) but rather on what gives us the potential to continue growing as human beings while sharing that growth with others.

      • Sam says:


        Let me know your thoughts after you build a business and go through growth with over a hundred customers and tons more people want your services. It’s nice but gets very daunting.

        I’m going to tell you a secret. Most people who say they dont care about money don’t have money. I’ve been there and I understand why. I encourage you to build a business beyond just being a blogger and freelancer to gain more perspective.

        I agree with you on outsourcing the thing one dislikes. No argument here.

        Good luck Raam!

        • Raam Dev says:


          I’ve helped run two corporations and three small businesses in the past 15 years, including a real estate investment venture and a wholesale distribution business that included international trade.

          I’ve been running a small web hosting business for the past six years which currently has more than 60 clients. I run it in my spare time and I’ve only used word-of-mouth marketing because I’m intentionally keeping it small; it’s my passion business and I’m not in it for the money.

          I’ve also been freelancing for the past 15 years and I have, many times, experienced far more requests for my service than my available time allowed for. I know what it’s like and I’ve learned how to say “no” (although a bit more politely than that) so that I remain happy instead of feeling stressed, instead of feeling like I sold my soul).

          When I hear “let me tell you a secret” and then something about money, I’m immediately reminded of how fulfilled I felt when I finally released all desire to obtain more money. (I didn’t always feel that way… for most of my teens and early 20s, I was all about money).

          Money is nice, yes. Money can help us do stuff, yes. But money doesn’t buy happiness. Money doesn’t buy peace. Money doesn’t buy us success (success is what you decide to make it). When we have *enough* money, more money does absolutely nothing for our overall wellbeing. Recognizing how much money is “enough” is the most important lesson I’ve learned since I started my first business at age 15.

          These are lessons I’ve learned the hard way, through success, through bankruptcy, through working 80 hours a week at two jobs while doing consulting on the side.

          Business is more often than not associated with money and I believe that it shouldn’t be.

          Business should be associated with focused activity and business people should be people who focus their activity on things that matter to them. I believe that in the end, money does *not* really matter; what we do with that money, what we do with our time, and what we do to leave a legacy, that is what really matters.

          Thank you for your response and thank you Conni for allowing me to share these experiences here. We all have our own journey to take and I’m all about learning through experience. :)

  9. Hell yeh! FYF!!
    Conni, it's great to see such clarity and passion. I'm in the midst of a similar transition and have so many of these same questions. You've given me lots to think about and have really helped to confirm that we can do this! Life can be lived on our terms rather than in a way we feel is expected of us. 
    You're so inspiring and I look forward to sharing the journey.

    • Conni says:

      Hi Peggy! Great to have you on my side :) and thank you so much for your wonderful words! Glad to hear I can be of help with what I write here, means a lot to get the positive feedback!

      Two things that help me move forward with my plans: My own ideals, that I just can’t give up, and my reluctance to give up my life and freedom to things I don’t like or enjoy or don’t believe in! The more I internalise that, the more I HAVE to change the things I don’t want to accept.

      We can do this, Peggy.


  10. Janet says:

    Found you via Benny's tweet. And great post!! I love that you are going head on into this!! I totally believe YOU can pull it off! I just quit my job about 3 weeks ago… But I was only there for a month! I quit my LONG TERM office job 2 years ago and made the travel plunge in 2010. I'm still surviving and freelancing too! Sometimes I wonder if I can pull it off. The first 6 months were TOUGH but I think things are looking up! In fact, that's why I quit the lame 1 month job… It was silly and didn't make sense for me to be taking on a low wage third world job making $2/hr when I was making more in client work!! Hell yeah!! And that's why my plan to live in the Philippines while I "build my empire" is strangely a smart thing (at least I'd like to think so!). I can survive with very little and even $300/mo if I have to! I'm not making an income I could survive with in the US atm, but I'm making much more than $300! :) Anyway.. GOOD LUCK! It makes me happy to know that someone else is taking the leap!!! Weeeee

    • Conni says:

      Hey Janet!! So glad you found me, which means I was able to find you and your blog as well – brilliant! I think we might have tiny wee bit in common ;)

      You absolutely go, girl! That’s the spirit and the attitude, love it. Where abouts in the Philippines are you? Planning on heading over there sometime next year as well, been on my agenda for a while. Good diving there too ;)

      Let’s keep in touch!!

  11. Tom Pinit says:

    Wow Conni! Wow! :) So much great stuff in that post. Life-life balance, FYF, and that TED talk you shared with me a while back. Your mom's site is lovely too!
    You're an inspiration, thank you. Very exciting times, can't wait to hear more about it as you move ahead!

  12. kara rane says:

    hi Conni-
    thank You. Living in an Earthen Home now. If we would all live our happiness- from truth within- we could return the world to beauty and meaningful purpose.
    Welcome to the Revolution