• The Friday File
  • Posts
  • What you need to do before you leave your W2...if you can help it

What you need to do before you leave your W2...if you can help it

I am a firm believer that you are going to have to eventually pick your W2 or your freelancing goals. Here's what I did to prep.

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 reminded us on the regular 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 actually at least as (if not more) secure than the W2 that 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, it was obvious they’d be mandated for government workers. I had made a pact with myself after leaving the military 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.

The point is that you need to get off your haunches and get started. That way when it all goes to crap, you already have something going. Maybe you don't have much going at first, but you will learn how to leverage scale, and when you do, it will be dynamite.

Make sure to check out my ebook on getting started, and start pulling in those benjies now.