Until relatively recently (the past few years), I was too uncertain of my skills to do much of anything for myself.   I felt trapped by my own ineptitude. I wouldn’t move a piece of furniture, lest it be a wrong move. I tolerated bad designs, kept all the default setting on my computers and faithfully followed patterns.  My first baby step towards hackerdom was when I felt I knew enough about cooking to start making some substitutions the first time I made a recipe.  Then I extended that freedom to baking.  First breads and then quickbreads & cookies.
The jump to messing with recipes with chemical leaveners was a big one.  There is a lot of chemistry involved in changing those recipes and getting them to still work out right.  Just ask anyone whose cakes have collapsed or cookies that just melted all over the baking pan.  I still avoided complicated knitting because the complicated patterns intimidated me.  It took me years to be willing to knit my first lace pattern.  And then, it was like something in my brain shifted and I found myself completely unable to follow recipes or patterns, regardless of how well I understood the process.
This anarchistic approach worked for me because I was fine making mistakes. Even if they were big, Ii now need to rip out an entire project” mistakes.  I suddenly understood that it was the process I enjoyed.  Successfully completing a project was just the proverbial icing on the cake.  I now sew, embroider and weave having taught myself by jumping into the deep end of the pool.  Has everything been beautiful? No. But I have learned from every step, whether successful or not.  I learned the reason for the rules and conventional wisdom the hard way.  But in a way that allows me to use all of my new knowledge as a jumping off point for my next project.
Hacking technology seemed like an unconquerable frontier.  I think it is because I know so many folks who know the ins and out of hardware and software that I was just intimidated.  Not intimidated of my friends. Intimidated by the prospect of asking for help. In hindsight, having knowledgeable friends is an asset.  It is much easier to jump in to the deep end of the pool knowing that there is someone standing around with a life ring.  Even if you know that you won’t ask for help unless the situation gets dire.
Fast forward to last year, right about this time.  I hacked a Nook color into an Android tablet. I hit some snags in that effort,  but I pushed through them and my success was intoxicating.  Then I hacked a Canon D10 for a friend who wanted RAW, rather than JPG format. Then I started restoring and upcycling the random detritus in our home.  Rather than discard a nice, but increasingly bare, cat condo, I recovered it in upholstery fabric.  Now I am ready to tackle gutter repair.
I won’t offer trite advice about overcoming fears.  Instead, I suggest taking baby steps out of your comfort zone.  For some people that means something big, for others it may be as simple as trying a new dish at a favorite restaurant where you always order the same thing.  Just take that step.  Who knows where it will lead you.