I'm Ready to Jump... What Now?

This post is all for you, you who are feeling disillusioned with life. You're trapped in an endless cycle. You feel feverish determination, finally yearning to make a change one week but the next week you're back in your 9-5 job, same life, same schedule, that disillusionment forced into becoming, yet again, a tickle in your thoughts... numb to it all.

Let's grab some initial realities: that catalyst you've been waiting for doesn't happen without your influence. No one is going to change your life for you. Luck is some cosmic crap we feed ourselves: you are in full control over your situation and, as I said earlier, it's not as simple as "just go" but it is as simple as making small efforts at a time: “luck favors the prepared.”

You can do this. Let's talk about how.


Here's our initial problem: I don't know you nor your life situation and I don't want to waste your time with general advice. I am going to try my best to keep to useful advice, but please please PLEASE comment if you're feeling stuck and need more help that caters to your freelancing wishes. We're all in this together.


Let's first acknowledge where your headspace is. You might feel an sort of existential anxiety: what have you been doing, why haven't you done what you've promised yourself for years, etc.. Perhaps you're looking back on this year having expected to be a different person, be in a different situation. Maybe you've been wanting to work for yourself, you aren't doing as well in school, any number of negative, situational feelings.

First, let's recognize that this feeling is okay.

You haven't failed in life, but, perhaps, you have failed yourself, and it’s earth-shattering, ground-breaking, the worst feeling in the world, right?

Now, you will grow to like failure… seriously. Failure is part of the process. Even after you’ve got it all figured out, if you aren’t trying something new and failing, you aren’t making progress. Failure gives birth to success: try a bunch of shit, fail, pile high those failures and use that hill and climb to the top.

Anyone who offers you a one-click, no-fail solution is selling something.


So you want to finally make the jump and change your life. As this article is catered to freelancing, let's grab some initial steps on how you can acclimate comfortably, and then execute.

I think the first thing you want to do is pick a range: do you want to be a travel photographer? Write political articles or fantasy books? Become a renegade marketing badass for large companies? This may take time to consider, but remember that this isn’t a straight line to success. You are going to change your path any number of times.

Choose your direction not your destination.

Now let's be honest with ourselves: take a look at your life situation and how much time you've got. Do you spend your freetime pursuing the career you want? How much Netflix do you watch? How stressed are you? Why?

These are important because you've got to find room to nurture your new path. If you're stressed out by school, bills, mom and dad, and you don't find comfort in your future endeavors, well, you have an uphill battle. Certainly not impossible, but here’s what I’d recommend.

Identify what stresses you out. Identify what your time sinks into. Become aware of your life 'cause actually seeing what you do with the 24 hours a day allotted to you can cause a completely different existential crisis that might drive you to make the changes you need anyway. Identifying failure (if you see spending six hours a day on Netflix as failure) is a base for growth.

There’s another issue of stress. You might have kids. Maybe you’re the only source of income and other people rely on you. You look at your schedule and can’t figure out any time of day you could squeeze in what you’d like to be doing. If this is true, if you haven’t got any freetime or wiggle room, I hope you at least treat yourself to a massage every so often ‘cause that’s awful.

BUT, I think you can find at least one hour a day to manage your social media, write, take photos during your job, during your break, film your life, all depending on what you’d like to do, of course.

Make small changes. Start somewhere.

I hope that by making small changes, you are able to eventually identify how stress affects your life or, more importantly, how it keeps you in that cycle of crisis and numbness.

This is probably going to take you some time, so take it. Again, small changes.

When you've got a better analysis of your situation, let's talk about action steps towards your future.

Freelancing is a pain in the butt but, oh my god is it worth all of the effort and it will start to take on a life of its own. First thing I do for my friends is evangelize a bullet journal or any sense of organization for your thoughts and schedule.

Get organized.

I will write another blog on my 2019 bullet journal setup. Some pages I would recommend for starting freelancers include:

  • Goals Quad

  • Big Moments and Accomplishments

  • Social Media Tracking

  • Blog/Writing Calendar

  • Content Brainstorm

  • Time Log (to track how you spend/waste time)

Tweet me if you want to see some quick shots of my Photographer Bullet Journal examples.


Here’s the big tactical move and I’d like to explore this from the perspective of a budding freelance writer. You have this entire writing universe, your mind has ZERO direction on where to go. What direction did you opt for earlier? A fantasy writer? COOL LET'S GO!

In your freetime, put down Netflix for two hours and write. I would start with short stories. You’re a fantasy writer, so write fantasy that you think caters to a large audience. Cool, finished?

This is what's about to make you a true freelancer: research and research and research. Start with Google - "Fantasy writing magazines." You've got 500,000 search results to choose from. Pretty overwhelming right? Small steps, 1000 journeys, baby!

Click on that first link, which is probably some huge, scary, well-established company you have zero chance of publishing to.

Does that stop you? NOPE.

Find their submissions link.

Open a document and write down the magazine title, copy-paste their submission requirements, the link to the submissions page, extra bonus if you can find the editor's information. Write everything relevant down: if you don't use it now, YOU WILL. You think your hard work ends here or in the personal inbox of the editor, hello? Dream big, sweetie.

Once you've noted this site's information, assuming you've met their submission requirements, submit. You might feel like you’re in trouble because you’re submitting to a scary-established publisher who might write you back for being ridiculous. Why would they want your crap? I felt that way. I STILL DO. That’s anxiety, fear, and remember what we do to fear?

Rinse and repeat with link two back on Google.

Do this 100 times.

It'll take hours.

You'll get 99 rejection letters.

One magazine will show up in your inbox with more questions and ask to edit the document with you on Google Docs.

That one magazine will work with you. They will help you polish your short story to a shine and you will learn so much without spending a dime. You’ve got to remember that even though you spent six hours compiling a list of publications only for 99 rejection letters:

One will publish your work.

This is actually what happened to me the first time I started submitting my travel articles, and have you seen the way I write? The point is, submit 100 emails, get 1 positive back. That 1 positive becomes 2 becomes 8 becomes 20 as you grow and learn.

Bonus: now you've got a compiled list of contacts so you can spend 1 hour submitting a batch instead of 6 hours.

The same theme goes for most freelancing I can think of: find the companies who want your support, and support them with your content. Join forums, enter into contests and galleries, follow relevant Twitter accounts, be social, be active, stay in your lane and practice practice practice: you will (probably) end up shifting courses as you find your style and voice, but what's important is taking those first few steps.

It’s a start. If you're doubting yourself and your future, this is a small sacrifice of time for a huge boost in emotional return: that first acceptance email is everything. If I had a house and a printer, I would print out all of my rejections and tack them to the wall in front of my desk. I'd print out my acceptance letters and tack them next to the rejections. The rejections are piled high right now but I have confidence that I've got the passion and integrity to exponentially grow that pile of happier news, confidence that grew from many more failures than success stories.


It all starts with that feeling of impossible angst. Do not adhere yourself to it: use those negative feelings to work towards the future you owe yourself. Identify your struggles. Identify your ambitions. Find what you can sacrifice to make it happen no matter how slowly or how useless it all seems. Progress is slow and agonizing and hard.

Most importantly, get organized. Not only does it keep you honest, but it is a visual enforcement of the progress you've made.

Those are all the hard parts. The actual work is 10% of the struggle at first. You'll find out. You'll watch yourself emotionally struggle with not doing enough, going back to Netflix for that extra hour, not touching your work for weeks on end. It took me a year to put down over 40 hours of Overwatch a week with Bullet Journaling - I’ve still got the page, the week where it all clicked for me.

Remember that change isn't instant. Failure only as good as the lessons you learn from them. You will fail 99 times and succeed once. The trick is not to get discouraged.

Freelancing is 10% work, 30% effort, 60% endurance.

You can do this.


If you’ve already gotten started with freelancing, leave me a comment about what your initial journey was/is like! I love the way you guys hustle, but I like seeing those success stories even more!


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