Molehills Out of Mountains

Hiker overlooking a Rocky Mountain vista

For the first time this year, I paid self-employment taxes and submitted a business profit and loss statement along with my 1040s. While I’ve earned money from various side hustles in the past, this is the first time I’ve filed as a sole proprietor.

This stuff used to scare the shit out of me. I put off getting serious about my self-employment income because I imagined the bureaucratic steps involved required an army of attorneys, an arsenal of accounting tricks, and a little hoodoo magic.

I’m not going to pretend to be a business tax expert. I couldn’t tell you whether or not you should deduct windshield wiper fluid or that giant inflatable squid.

Rather, I want to share one simple point:

Don’t let something simple stand in the way of working on your microbusiness (or your creative project, or whatever)

Not earning self-employment income because you don’t want to file self-employment taxes is like not eating because you don’t want to chew.

Filing self-employment and business taxes might appear intimidating, but that’s only because it’s a new and unfamiliar experience. Now that I’ve done this, I can happily report that the challenge level falls somewhere between partially shaving your cat (don’t ask) and writing a breakup letter to someone you only kind of sort of care about.

Stuff I used to find intimidating

Think about something you once dreaded doing but, after you did it, looked back and said ‘that wasn’t so bad.’ Here are a few that come to mind for me.

  • Getting married seems scary, but it turns out the horror stories about your life ending are just that: stories, full of sound and fury and usually told by idiots.
  • Traveling abroad for the first time seems intimidating, but after a few trips, you begin to look forward to handing over your immigration paperwork and the occasional petty bribe.
  • Classroom teaching is scary, but after you learn some classroom management it becomes an enjoyable exercise in communication.
  • Changing a car’s master cylinder seems intimidating but, after you do it, you realize the hardest part is not dripping brake fluid on the paint.
  • Recording your business income and expenses is intimidating, but it turns out to be just an exercise in accurate data entry.

Why does that which appeared challenging in foresight prove itself easy in hindsight?

Because jumping right in and learning through direct experience is the fastest way to remove the uncertainty from any venture.

The unknown will always be intimidating. That’s just the nature of the game.

Waiting until you’re better equipped to face the unknown is a classic catch-22. Experience is useful and necessary, but the only way to gain experience is to actually do something.

Information is overrated. Reading about a topic will only take you so far. Waiting until you have more information is usually just an elaborate exercise in advanced procrastination.

The fastest way to turn a mountain into a molehill is to do that which intimidates you.

 

Talk to me

What mountains have you turned into molehills? What molehills have your turned into mountains?

 

Photo credit: ZachDischner

 

Comments on this entry are closed.

  • I love this post, Seth. Just right now, in fact, I’m fighting Resistance every day to get a creative project off the ground that’s been brewing for … oh, about 8 or 9 years! It’s been a really fun experience. (I’ve only started again twice, I think.)

    Thanks for reminding me that it’s important. And also, I was talking to my wife (you’re right, marriage isn’t as scary as all that) the other day about how I read somewhere something like:

    “The best excuse that people come to me with for not starting their own business is: I don’t know anything about taxes. To which I reply: if you’re paying taxes, something’s going very right, and you don’t really need to worry about it.”

    Mostly, these things are excuses, I think.

    I’m so stoked to turn one of my biggest mountains into a molehill in the next week or so.

    Thanks again.

    Peace.

  • Anonymous

    Thanks for sharing. Like you, I’ve found Resistance is really really good at turning simple challenges into lame (but for Resistance highly effective) excuses.

    I even used the “I don’t know anything about taxes” excuse to delay setting up my business. Paying them was indeed a happy hit to the forehead (me saying “Nice! My business made a little money!”)

    Keep us posted on your project.

  • Tom

    It’s true that we do make a big deal out of things, that later on turn out to be relatively easy and never end up as bad as they seem. By the end of this year I should be going to South America and a part of me feels this may be a difficult experience, but the other side of me knows that after a few days I’ll settle in, get used to the differences and have good fun.

    I’ve also been procrastinating with my personal finances a little, and to be honest, I know I am making a mountain out of a molehill with regards to dealing with investing. I’ve got one good personal finance book that I know has all the info I need, and I will read it and implement the strategies.

    I guess it’s always a good thing to bear in mind that intimidating things are never that bad and that we always tend to grow as a result of breaking through the painful period and getting out of our comfort zones. Great post Seth, very useful to me.

  • Tom

    It’s true that we do make a big deal out of things, that later on turn out to be relatively easy and never end up as bad as they seem. By the end of this year I should be going to South America and a part of me feels this may be a difficult experience, but the other side of me knows that after a few days I’ll settle in, get used to the differences and have good fun.

    I’ve also been procrastinating with my personal finances a little, and to be honest, I know I am making a mountain out of a molehill with regards to dealing with investing. I’ve got one good personal finance book that I know has all the info I need, and I will read it and implement the strategies.

    I guess it’s always a good thing to bear in mind that intimidating things are never that bad and that we always tend to grow as a result of breaking through the painful period and getting out of our comfort zones. Great post Seth, very useful to me.

  • Anonymous

    Like you, I’m a notorious personal finance procrastinator, but over the past few months one of my projects has been to build a personal finance system. Since February I’ve added a business banking account and another personal bank account, setup a Roth IRA, and made it a point to buy a couple stocks every month.
    I too put this stuff off for ages, but now that it’s done, I see it wasn’t that hard.

    I don’t know if you’ve seen it, but Ramit Sethi has a great post on Tim Ferriss’ site about setting up a bullet proof personal finance architecture: http://bit.ly/aobPKc

    South America should be an outstanding trip. Yeah, it will be difficult, but you’ll most likely have a great experience. Do you speak Spanish?

  • Tom

    Ah yes, Ramit’s stuff is awesome, I’m reading the British edition of his book right now. I like his no-nonsense approach to finance.

    I do not speak Spanish, but I am going to brush up my skills beforehand. I’ve also been looking into teaching English and I’ve read some of your posts about teaching English abroad, very useful!