Decisions are hard. Especially life changing ones. But in the end, our decisions (or the lack thereof) define our character and how well we can spend our time with stuff that we enjoy and love.

Also there is the saying: Hard decisions lead to an easy life, whereas easy decisions lead to a hard life.

I had internalized this concept that if I want to have more of the things I enjoy and that motivate me, I have to make some really tough decisions in life. And it helped me tremendously in my social and my professional life.

So the question is, how can one make this process of making hard decisions a little easier? In this post I want to show you a technique that helped me to achieve just that. I will illustrate this with the example why I chose to become a freelancer.

As I was studying at the University and later as I started to work as an employee at a company I always knew I wanted to be a freelancer. In those days I rationalized it with the idea of being free, or at least more free than an employee. So I decided to ask myself how to achieve this goal. And fooled myself into thinking I made a permanent and solid decision.

I started learning all the things so to speak and my skills improved day by day, but with each topic I gathered knowledge, I felt that I knew less than ever before. So I questioned my decision, looked for other ways, had periods with less focus and in general fluctuated in my mood and my ideas how to achieve the goal as fast as possible. So I needed all the energy to think about the decision on and on. And I know that this is a feeling a lot of people have. In this process I asked myself lots of questions like:

  • Where do I get my projects
  • How much upfront capital do I need
  • Which technologies do I absolutely have to know
  • Which other skills (like people skills) do I need?
  • Am I good enough, not just technical but also in social skills
  • Do I know my worth, and how do I figure that shit out
    …and many more, and all in a cycle many times over

Until I realized that those are not the right questions for the situation I was in. So because I did not get the feeling to get any closer to my goal I simply took a step back and asked myself what did I do wrong here?

Ask yourself WHY before everything else

And with a little thought and reflection it struck me. I never truly asked myself why I wanted all this. It simply felt like I wanted it. And that is the most important point of this post, and one of the most important techniques one can learn for decision making in any area of your life in my opinion:

Separate the decision in two parts.

  1. Figure out Why you want to do or achieve something first
  2. With the clear vision of the Why, you will always find the how, hell you mostly even do not have to look at it a second time.

Another important part of this process is that you never dwell over the why again. Figure it out and then concentrate on the process and action. If you do not find a clear vision, maybe you did not want it as bad as you thought. And that is a very good thing to recognize as well. This is obviously the ideal situation, life changes and your views on life might change, and that is totally fine this way. Just make sure that this does not happen every other day.

Although nothing is off limits, the only person that can tell you why you want something is you. If your why is to impress other people and this is so strong for you that this is what keeps you awake at night so be it, if it is personal gain, money, fame or whatever all that is ok (at least from my point of view and as long as no one is harmed in a direct intentional way), do not try to rely on “wisdom” of other people or social norms. Because those things change faster than the direction of the wind does.

But you may ask, what the eff? How do I find a why? This is the hard part actually and most people confuse the how for the hard part, but if you know why you want something, you almost feel physical pain if you do not go for it. And then you will always figure out the how as I mentioned above.
So to find your why for anything, think about what you want in life. I know easy right?

So because I know how hard it is to identify what one wants, and most people in the modern world, me included, are all but experts in being reflective with their wants and needs.

Ideas to help you find your why

To give you some inspiration, I will present you four methods to free yourself from what other people think and from the constraints you and other people have given you over the years.

  1. Imagine what you would do when you were independently wealthy and all people would forever like you by default whatever you do. Just imagine that for a second and ask yourself the question why you want a particular thing.
  2. Start with the things you already know about yourself, like with my example I knew I wanted to be more free and have a life where I experience new stuff as I go along and have to challenge myself in different environments (professionally and socially)
  3. There are two emotions where you can find your why for a decision. The first one is fear and the second one is need. Arguably they reside in the same part of you, but look in different directions so to speak. So think about the things you are afraid of, and try to figure out if that motivates you
  4. Imagine you lie on your death bed and think about this decision, which one of the options not taken would you regret the most? That might not be the actual decision but it might spark some new thoughts…

So to identify your fear/need that drives you, you have to ask yourself questions and have to get to know things about yourself. And you can always change your view on life and the things around you and that is totally fine, no one will judge you because most people are occupied with tehmselves more than anything.

How it was for me

So with this techniques mentioned I want to give you my personal struggle to find a why:
As mentioned in the beginning during my search for the why of being a freelancer I listed all the things I saw beneficial of being a freelancer, so I somewhat started from a rational point of view instead of an emotional one:

  • lots of work with interesting people
  • working in different places
  • learning new and “cool” stuff
  • helping people on the way to make their life easier
  • working on projects that I choose
  • earning more money (duh)
  • having a company and the benefits that come with it
  • status
  • confidence
  • more control over my time (really?)
  • it is in the name goddamit: free-lancer
  • relatively easy step into enterpreneurship ….

But nothing of those things, although they seem all like reasonable aspirations, stroke me hard. Then one day, as I walked to my current job it hit me like a baseball bat.
I knew why I wanted always to become a freelancer, it was the same reason I left my hometown to study and guided most of my decisions up to this point: Growth!

Not just growth in the sense of money or power, but in the sense of curiosity and knowledge. I always felt most alive when i learned the most and was pushed to my edges.
And as a freelancer all the above would lead to this exact goal.

With that said, I was still scared shitless of quitting my job and going for it. Yet now my yearning was so intense I could barely tolerate to wait for it, although people told me to gather more experience and so on and so forth I simply went for it. On the other hand I also had a moment that sparked all that in my professional career as an employee when I simply realized I do not want to do this a single day more than necessary.

Should you apply this concept for everything?

So in essence for all major decisions in life I personally try to apply this technique and ask myself why before the how. But with everything in life, do not overuse it. I think much of the smaller decisions in life, or maybe some that might simply yield some fun times, you could simply go with your gut. But it is up to you how you use this tool.

Also I cannot tell if that works for you as well as it did for me, but that might be part of this process, try some new ideas and concepts to make your decision making process easier.


In this post I showed you a technique which helps to make hard decisions easier (but not easy). This boils down to asking yourself WHY you want something before asking yourself HOW you can achieve that aspired goal.

I illustrated it shortly with my personal story on how I decided to become a freelancing software engineer.

Categories: Freelancing


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