Three lessons for your journey

Lesson 1: go all in

Look, I’m going to shoot it to you straight: if you don’t want to succeed and grow, then decide just to do this on the weekend or whatever. You’ll do great, maybe picking up a gig here or there, and there is nothing wrong with this. In fact, I can even help you get started on Upwork; some people hate Upwork, but it’s helped me a lot along the way.

However, if you want to sink your teeth into this lifestyle, you must make it your sole thing.

Allow me to explain.

When you have a fallback, avoiding the painful and difficult things that must be done for growth as a freelance writer is easy. I will not sugarcoat it: sometimes, it sucks and is hard. You stare at a blank page, scroll Twitter for a while, check your email, and when you come back your page is still blank.

Unlike a 9-5, nobody pays you for a blank page. A blank document is still worth zero dollars whether you charge $0.05 per word or $0.35 per word.

But when you have the safety net of a W2 job, you can always push back your products to the next day. And then the next day. Then the one after that.

I know this is what happens because it’s what I did. And it wasn’t for a short period either; I started writing in early 2016 and didn’t take the plunge full-time until April 2021.

My first job as a freelancer. At the time, I had no idea how huge this was.

Had I known what kind of potential I was sitting on, I would have thought seriously about jumping ship and striking out as a freelance blog writer full-time way back then. But there was always this nagging fear.

Look, it’s reasonable to be afraid of quitting your job to pursue this. But I am telling you, you will not see your potential start to develop until you throw yourself into this thing entirely.

At some point, we all have to decide if our side hustle is just a side hustle or if it’s our future. You are the only person who gets to decide this.

Lesson 2: you can’t be a prophet in your hometown

The first time I saw this statement, I thought to myself, “what in the world is he talking about?” But then I thought about it a little more.

Why is Twitter so popular for moneymakers to do their thing instead of Facebook? Because Twitter is completely location-independent. Who makes up most of your Facebook following?

Friends, family, acquaintances. It is made up of people who know you on a more personal level and maybe some folks who have known you long before your entrepreneurial life. They may be the type who will publicly question you, your content, your motives, and your abilities. They may even be the type to criticize you about them.

Twitter kind of levels the playing field. To be honest, I think there might only be one or two followers of mine who live in my state, and none know me personally.

Instead, we get a platform to seek out people with similar goals, and interests easily, and openly share our trade secrets.

Do I think you can’t be a prophet in your hometown? You could, but it’s much easier when you put yourself out there where people are already looking for what you have to offer.

If Not Your Town Square, Then Where?

LinkedIn has become so wildly popular because anyone from anywhere in the world can connect with you. There are no notions that you are there for any reason other than networking and finding work. It’s that simple.

It became the new town square, although, to an extent, so has Facebook (private groups post thousands of gigs and jobs), and Twitter is full of entrepreneurs and solopreneurs. Building an online brand is clutch and couldn’t be any cheaper.

Everything is at your fingertips, and it’s free:

• Newsletter: Substack, Beehiiv, and many more all start for free.

• Twitter, LinkedIn, Instagram, TikTok, Facebook, and so on for building communities. You can recycle your work from one platform to the next, only polishing it and formatting it correctly from one to the next.

• Email and word processing: use Google Suite. It’s free, added storage is dirt cheap, and everyone uses Google.

Building your brand online opens the whole world to you and your endeavors. You aren’t limited to Sandusky, Ohio, or Salina, Kansas. You can be anything you want, anywhere in the world. It’s rad.

Lesson 3: build before you leave your W2…if you can help it

The best thing I did for my freelancing career was to start seven years ago.

The worst thing I did for my freelancing career was to linger at my W2 job for years too long.

Striking A Balance

So when should you walk away from your job? That’s up to you. But at some point in time, you have to make a choice: pursue it with everything you have, or walk away.

I know that some people will tell you that you can do both, but you probably can’t. Maybe some people are made of stronger stuff and can multitask both, but in my experience, you will reach a point where you have to make a choice.

When you have that W2 to fall back on, it does something to you: it makes you feel comfortable. It provides a false sense of security. You are infinitely replaceable.

Years ago, I worked at a Target distribution center. Thankfully for me, I only worked there for two years, but it was the longest two years of my life. I hated every single day of that job. It was life-sucking and soul-crushing. Our group leaders regularly reminded us that there were about 10,000 people in the city who would take our jobs, no questions asked.

The point is that no matter what you do, you can and will be replaced. I worked at my last job for 7 1/2 years. I slept in my office more times than I can count because of long nights. My entire workplace (an airport) was completely submerged in the Missouri River twice in 2019.

After all of that, I didn’t even get a card when I resigned. Nor did my bosses take me out for lunch. Nothing. I had nothing but glowing reports and feedback from our customers. Still, not so much as a going-away card.

I’m not bitter. I just want you to realize that the solopreneur or freelancer journey you’ve embarked on is at least as (if not more) secure than the W2 you are scared to leave. They don’t care. And If they claim that employees are family? 🚩🚩🚩🚩🚩

What does this have to do with striking a balance? Unless you are working for family or a local mom n’ pop shop, you should have no qualms about sticking around long enough to meet your financial needs or goals, then punch out. It’s all part of the culture.

What Is The Balance?

Ideally, holding out long enough to match the pay you’re leaving would be ideal. But it isn’t always ideal.

Moment of truth: we all remember that thing that happened in 2020. When the vaccines were rolled out in late 2020, they’d obviously be mandated for government workers. After leaving the military, I had made a pact that I wasn’t getting inoculated with anything that I didn’t want in my body, and this was no exception. Thankfully, I’d been building up my hustle for several years, so it seemed like a good time to take the plunge.

Whatever your take is or was on the vaccines, you can see my point: you need to make sure that you are in a position where you can leave on your terms, not theirs.

So, How Long Should You Wait?

I speak strictly from personal experience, but the longer you wait, the less likely you will pull the trigger. You need to do this as quickly as you can because the only way to learn how to scale is to do it. If you aren’t relying completely on yourself, you won’t do what it takes to make it.

Growth is found when you have to make it. I did not grow at all until there was no choice. After walking away from a government job, there was no going back to a depressing office. It was make or break, and I’m making it now.

Ideally, though, give yourself a concrete departure date. Work more, build up your side hustle, or sell stuff to ensure you have some cushion in your bank accounts.

How you decide to transition from a 9-5 job to freelancing is up to you. But beware of what you will lose:

• Annual leave

• Sick leave

• Bonuses

• Salary

• Health benefits

Personally, I don’t miss any of these too much. The hardest has been annual leave. However, the key is to enjoy what you’re doing enough not to need frequent breaks. But sometimes you do need to get away.

The best way to combat these feelings is by learning a high-paying skill and increasing your cash flow considerably. Keep your expenses down, increase revenue, and allow yourself time off because you made up the difference in excess cash.

Parting thoughts

Thanks for dropping in today. Freelancing is kinda scary, especially that first year when you realize you bet everything on this one thing.

But hey, life is one big risk. You'll be fine if you are calculating and do your homework, and crush it with a strong work ethic.

Oh, and make sure you’re likable. This is a way-overlooked quality.