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The Beauty of Freelancing Until You Hit the Big Time Freelancing it a bridge across the chasm separating day-job security from entrepreneurial opportunity.

By Daniel DiPiazza Edited by Dan Bova

Opinions expressed by Entrepreneur contributors are their own.


So you want to start your own online business?

I'm not going to sugar coat it, sell you rainbows and unicorns or tell you that becoming an entrepreneur will make you instantly rich. And I'm definitely not going to tell you that it's easy. Starting your own online business is HARD. The biggest component to success is a high-risk tolerance.

I have repeatedly struggled to find my footing, pay bills and get everything set up before finally finding a workable formula.

Being a Rich 20-Something is more than just a money-driven hustle.There's a big learning curve that goes into it.

The business itself is easy to create. It's the cultivation of the business that takes time and energy. No matter how great your idea is, it will not flower by itself. You have to nurture it.

So here's the problem: nurturing takes time! Lot's and lot's of time, attention, care and energy.

"But I don't want to take a lot of time getting this thing started. I want to quit now, not later…"

I get it. And trust me when I say I feel you.

My goal is to help you harness digital power to make yourself money with as little effort as possible. Create products, share value with people, make income. But it's not a linear process, is it?

So how do you make a relatively smooth transition from corporate employee to automated/digitized entrepreneur without going destitute? You have to start with the middle road: freelancing.

Related: Should You Quit Your Day Job and Jump Into Entrepreneurship?

A little something on freelancing…

First and foremost, as much as I hate, despise, abhor, detest chained-to-the-desk and report-to-the-boss day jobs…I'd never advocate that you quit them before you have something viable in place.

That would just be dumb!

The bottom line is this -- you need time to set up your business. Most corporate jobs have schedules that don't really allow for the type of time you need to build content, products, relationships and skills.

In the transition period between quitting your job and creating your digital empire, working as a contracted freelancer is a great alternative to working in a rigid 9-5 system. You get to create your own schedule, meet a bunch of interesting people doing something that you hopefully love (or at least like)…and the biggest perk of all….

You can charge a LOT more money.

Most corporate jobs are salaried. They're going to max you out and overwork you for the same pay.

Hourly jobs are low-paying by their very nature. The more money you make per hour, the less the company will want you to be working. It's a Catch-22. (I think the exception to this was when I worked at UPS…those drivers are getting PAID).

But as a freelancer, none of this applies to you.

You set your own schedule and you set your own rates.

Related: 5 Ways to Make Enough Side Money to Eventually Quit Your Job

Inevitably, this is where the objections start to crop up:

"I have no idea what I would do. I'm not good at coming up with ideas."

"I don't have any valuable skills. I just have my job-specific skills."

"My market is already saturated. There are better people doing what I do."

"Nobody will pay for what I know when they can just teach themselves."

What are your skills?

There are literally HUNDREDS of things you can do that are enjoyable and that other people will pay you for.

I write extensively about this topic. To get your feet wet, start thinking about where you could mine your talent for freelance skills:

  • What do people consistently ask you for help or advice in?

  • Do you have any unique skills, talents, hobbies or abilities?

  • What areas of life have you excelled to an "advanced" or even "intermediate" level?

  • What skills and ideas interest you enough to learn, and then teach to others?

  • Could you work independently doing what you do now at your current job?

  • Do you have any friends with talents that compliment yours? Maybe you could team up.

Start little by little and leverage yourself before the leap (my story).

When I started freelancing, I was working at Longhorn Steakhouse (I'm basically a steak aficionado now). I was also working for Kaplan Test Prep.

My steak skills weren't worth much. But my Kaplan skills were.

I realized that people were paying $100+ per hour for me to tutor their student one-on-one.

You won't believe how much I was making…


And the worst part was…


Our perceptions are skewed because minimum wage is $7.25. So we think that anything significantly higher than that is good money. The reality is, $7.25 isn't even livable. You probably need a minimum of $20/hour to make it out here.

But when I really sat down to think about it…I just got INFURIATED.

Here I was, doing all the teaching, grading, talking, communicating with parents and driving from school to school while Kaplan just sat back remotely and took 82 percent of my money.


Since I was the one with the skill, I needed to be the one making the money. I knew I could make this work on my own and cut out the middle man.

So I bided my time. I looked around, I made some calls.

I found a partner who was also interested in getting a freelance education business going. He was the consulting side, I was the teaching side. Together we knocked down doors, created classes and started making money. A lot more of it.

First, I quit Kaplan. Didn't want any conflict of interest. Then, as soon as the restaurant started to get in the way of my new endeavor, I quit that as well.

When I quit both jobs, I wasn't making quite as much with the new business…but the projections were giving me a solid indication that things would pick up quickly. So I just took the leap.

So mine your skills, do your homework and take the leap. Don't look back.

Worst case scenario, you can always go back. Best case scenario, you'll never have to.

Related: 10 Questions to Ask Before Quitting Your Day Job to Run Your Own Company

Daniel DiPiazza is the founder of Alpha Mentorship and the director of the Profit Paradigm accelerator for agency owners.

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