Two and a half years ago I moved to Indianapolis with a very different thought process. I left Purdue near the end of my master’s degree with the intent to finish up remotely while working at your every day, average company doing something I love and working on Insanitek idly in my spare time. It didn’t work that way.

That sly look says, “You know you want some of this delicious tea.” And if you say no, you’re in for a big dose of push salesman approach according to their training manual. Image from Stephanie Sokol.

Instead, I moved at the wrong time of year, I didn’t start looking for work right away because I was busy moving, studying, and otherwise just taking care of all the crap in the moment. My window of opportunity started to close, and I didn’t even know it. My naïvety meant that all my carefully laid plans flew out the window, and thus I ended up at the mall in a seasonal job over the holiday shopping season.

It wasn’t a bad first job here, really. I learnt a lot about the people of the area, their mentality, and their spending habits. I learnt a little about Indy from my coworkers, where to go, where not go to, some fun places to check out — which I still haven’t gotten to yet. In other words, I used this time as a learning experience that gave me time to reflect on where I was and where I wanted to be.

I was making tea for a client as I analysed the path I was on and trying to find stepping-stones from here to there so my CV wasn’t lying fallow. I started to think more and more about Insanitek and take the idea of making this company something more seriously. Sure, I wouldn’t get the $55K out of school and health insurance that I was promised, but I’d be using my skills, my brain, and my passions. That was more important at the time than trying to coerce every housewife that wandered into the store into buying something by lying to them saying the tea will help them lose weight. (Which, sorry guys, it’s not a magic diet pill. You still have to watch you’re calorie intake. All tea does is increase the caffeine content in your body, which in turn helps your metabolism get ever so slightly revved up.)

Once you make a decision like this, you won’t go back.

Try as you might, once you make the decision to make this change in your life and go for what you want, it’s all-consuming. You start to think of your job as your “day job”, you start to think about your alt-path as your destination and journey all in one. You start keeping lists of what you need, what you want, and maybe  even make one of those photo boards to keep you inspired. You get your pay checks and start plotting about how much you can save for this or that to make the next step of the process happen.

Perhaps the most telling sign, though, is when you start thinking about quitting your job in all seriousness to make a real run at your new life. You’ll go through a few years of chaos where you question yourself, your mission, your abilities. You’ll feel fear, doubt, and anxiety as you tackle obstacle after obstacle.

One of the best ways I’ve ever seen this described is by Tom Morkes. It’s the best because it’s both light-hearted and geeky while being utterly true of both the entrepreneur and the alt-path maker.

Click to enlarge, click on Tom’s name for the whole story.

I can’t say I disagree on anyone point of this path. Tom has it down pretty well because he’s been there and still there in the middle somewhere.

The point is, don’t give up.

Remember all the good reasons that you’ve listed of why you should do it? Or the three reasons I gave you why you should do it? That’s all well and good, but how?

Move slow and steady. This is not the time to be brash followed by bull-headed. Take your time moving away from your old life and into the new. In fact, before you toss your letter of resignation into your boss’s face, take the time to think of the obstacles, then how you’ll get around them. Make a list of each fear and obstacle you think you may encounter. If you are honest with yourself now, you’ll have a better chance of as you work your way through that Conundrum Forest.

Each situation is different, and every solution will be different, so take a few days with each obstacle to write as many potential solutions, along with notes, for each problem. What I like to do with my clients is create a list table like so:

Amp it up by doing this in Evernote to keep webclippings of ideas and notes at your fingertips.

I put in a new row for each potential solution. I find this is easiest to help a client visualise their options. If you keep the notes with each potential solution, you can often find a place where they intersect, thus giving you multiple viable solutions for each problem. It really gives you the chance to think it through and see all the ways you really can make your dreams of an alt-path happen.

Learn some new tricks. While you’re sitting around at your old job biding your time, plotting, planning, and really scheming how you’re going to glide into your new future with confidence, take the time to make contacts, network, and learn as many tools of the trade as you can. You’ll be surprised how many people you can connect with now that you may call on later for their invaluable skills or knowledge. This is the power of a network, so don’t burn bridges while you’re waiting patiently to step out.

Likewise, while you’re there, invest in yourself to learn some new tricks, whatever they are. You could make friends with the IT department and learn how to set up your own website, the secretary down the hall to get some typing or organisation tips, or even take a few online classes and line those certifications all up in a row. Embrace the now, live life to its fullest, make the most of what you have, and give back to the company you’re with. When you do leave, you’ll leave on a great note that may even help you boost your new career.

Quitting like that can be fun, but not exactly productive.

Take one day at a time. Through it all, it’s best to take it one day at a time. There will be days when you love your job and think you’ll never quit, conversely, there may be days when you want to leave à la Office Space. Just take it one day at a time.

Even when you take the plunge from the proven path into the alt-path of your making, it can seem overwhelming from day-to-day. When that happens, take one day at a time, go one step further to create a system that works for you. With a system in place, you can take those one day at a time and amplify it to make the future you want.

Keep it in perspective. You wanted this path for a reason, and that is your perspective. Perhaps it is that you loved what you did, but wanted to tweak it a little to involve another aspect. Whatever it is that made you want better, keep forefront of your mind through the transition. It will keep everything, including the Bad Days, in perspective so you can still smile knowing you made the right choice for you.