The 3 Unglamorous Truths About Working for Yourself

I recently transitioned from freelancing to starting the foundations of a company. And boy, has it been an emotional journey.

Most of the time people get the wrong idea of what it is like starting or operating something that’s your own. Some common assumptions:

You must lovee what you do!

You’re so lucky you get to control your own schedule and work!

It must be so interesting day in and day out.

It must be nice to have people work for you.

Well I’m here to tell you that after a month of working for myself, it can sometimes drain the life out of you.

People that make it onto media stories will often tell you the things that inspired them and continue to do so, and how “hard” it was to get to where they were. Maybe they came from absolutely nothing, or they failed a couple of times before they made it. However, they don’t really go into detail of what that pain means, day in and day out.

Pain means not being able to see your partner or spouse when the day ends and morning comes.

 Pain means not having enough capital in the beginning that you have to resort to lower skill talent, endure countless headaches and money wasted.

Pain looks like not knowing on a daily basis if your efforts will result in anything and the constant self-doubt.

In the end, going through the unglamorous journey of working for yourself is a huge test of character. There are times where you feel like you’re breaking but you have to still get up in the mornings. There will be temptations to look elsewhere for different, ‘easier’ opportunities. Even if you don’t become as wildly successful as you or the people around you anticipated, if you manage to turn zero into at least a few moving parts, there is something to commend there.

Here are three things I discovered when I started working for myself.

It’s not only lonely at the top, it’s lonely getting there

People that work for themselves will always hold onto this sacred feeling of loneliness. I say sacred, because it’s a rare type of feeling that many don’t understand. 

You might be at a social event, and as you’re listening to the chatter about people’s work (whether it’s a 9-5, masters thesis, late night bartending job, or techie with PTO), you will inevitably feel a little out of place.

Starting something from scratch is scary because you truly don’t have anything to show for it in the beginning. It’s an unfinished vision you have to go and put your hard hat on to construct with your hands. And most of us, including your immediate circle thrive off a stable paycheck and security.

Neither of those things exist when you start out. And the ‘payday’ is some distant galore in the future, which you can only base off estimations and projections.

Fortunately, bringing an idea to life on the internet these days is much easier. Overnight, you can build out a website or obtain a thousand page list of leads using software. Hiring someone to do simple work is also easier and cheaper than once thought. Theoretically, it shouldn’t be as lonely because of LinkedIn, and there’s literally a million people working for themselves on there. But the truth is, the daily grind will be somewhat of a lonely path especially in the beginning. There’s no one to hold your hand and keep you accountable to what you set out to do. And rarely will there ever be.

There’s More Things You Hate Than Love in the Process

Regardless of what it is your passionate about—doing that and creating a system that supports that are two separate things. Let’s take real estate for an example. I love using the example of the real estate reality hit on Netflix, Selling Sunset, where you see beautiful, glamorous women trapezing around in luxury homes all day.

The truth is real estate is a grind and half. Most of the time you’re living in your car, “on call’ on the weekends, or on your ass phoning people left and right to try to secure leases, deals, making sure there’s no broken pipes in the house. If you’re looking to explore the aesthetics of a home, you’re probably better off as a stager or in design because most of what real estate is logistics.

It applies similarly for business. If you’re looking for only the “fun” parts of it; creating, designing plans, shaping culture, closing deals, you’re in for a rude awakening.

As my partner said recently,” most entrepreneurs love creating and innovating”, but the fact is most of the time you’re spent creating “systems” that will support your creative endeavors.

If you’re in it just to create and make beautiful things, you’re better off in a profession, seriously.

You Have to Get Used to Things “Not Going as Planned”

When I used to work in the events & entertainment industry, there was a common saying amongst event planners— that is, nothing ever goes according to plan.

As a religious planner, things that derail from the original plan is a big pain point. It’s something that leads to shame and disappointment within myself. This is also one of the biggest hurdle every person that works for themselves has to go through.

When things don’t work out the first time, or the third, it’s easier to throw in the towel. The problem is that we can only ever make ‘estimations’ about our expected outcomes. But, we don’t know actually how long it will take for something to come to fruition. 

Even if you have the resources to hire someone to complete a part of the project, hiring is a whole another behemoth in itself. Unfortunately, our expectations that someone will know exactly what we need, often falls short on our faces.

You might anticipate a website will be done in two weeks, and it ends up taking two months—which also slows everything else down. There are moments where it feels painstakingly still, and you have be patient and sit through it. And there will be a lot of times where you feel like scratching your hair out.

I view business similarily in the way of farming. You plant the seeds but you’re not sure exactly when it is they’ll sprout and turn into a big, beautiful harvest. It can take months of waiting and waiting. Except in business, there’s no waiting, but only constant pivots, micro-injections, and learning. It’s one big lovely experiment.

Conclusion

Although I wish I could tell you it was this glamorous, interesting life working for myself; the opposite is true. In a way, it is a job except it’s five times harder because you have no boss that expects you to show up, even on days when it’s really hard to get through the day.

As you might have noticed, I stray away from using the terminology of entrepreneur or entrepreneurship, simply because I think it’s overused and misconstrued with something superior or glamorized. I think these days, anybody can use any excuse to align themselves with that term, as if it’s some exclusive club.

I’ve come to the realization that when you’re truly good at something, and you do that thing day in and day out, it blurs into your life and identity in a way that you don’t necessarily think of labels when you’re asked what you do. 

What do you do?

I write,

 I create, 

I build and

 I love.