Ask Alex & Ellen: Should I Take The Leap To Freelancing?

I love giving advice.

So does my friend Alex.

We come from different generations and we’re at very different points in our lives and careers. But we share the same philosophy: every door can be unlocked.

Every once in a while, we  partner up on a special installment of my advice column, Ask Ellen. It’s called… Ask Alex & Ellen.

Two hits of advice in one column.

We hope you enjoy it!

Ellen Fondiler | Ask Alex & Ellen

Dear Alex & Ellen,

I’ve always wanted to freelance. I’m tired of playing by someone else’s rules, hours and holiday requests. I’ve never ever wanted to climb any ladder because I’m just not interested, but climbing my own ladder? That I can get excited about!

My partner just got the job of his dreams, which means we’re moving to a brand new town—where I don’t have a job.

Part of me is thinking, “Hooray! Since we’re moving, this is the perfect opportunity to kickstart my freelancing career!” But another part of me is thinking, “No. Be sensible. Get a new job in your new town and maybe do a little bit of freelancing on the side.”

I’m torn. Should I make the “big leap” into full time freelancing—or get a normal job and play it safe?

Leap Or Play It Safe?


Alex says:

Dear LOPIS,

As some who has been a freelancer for the majority of my career—and as someone who has watched numerous friends and clients make the leap from ‘having a job’ to ‘being self employed’—here is what I know for sure:

If you are self-employed, and you feel panicked, frightened, and desperate about booking clients and making money so that you can survive, your clients will sense your desperation—and they will run fleeing in the other direction.

I’m sure—at some point in your life—you’ve encountered a shopkeeper, sales person, coach, consultant, freelancer or entrepreneur who was just a little too pushy.

Maybe it was something about the tone of their website or emails or phone calls. Maybe it was the glaze of fear you detected in their eyes. Maybe they emanated a vague feeling of insecurity. Whatever it was—you could feel it. And it didn’t feel good. You didn’t want to hire that person—and why would you? They’re stressed! Who wants to hang out at a stress ball’s party? Nobody!

Here’s my point:

If diving into full time freelancing—without any “safety net” job to create a feeling of security—is going to turn you into a stressed, sad, panicked person, then don’t do it. Why put yourself through that kind of misery if you don’t have to? Building your freelance practice from a place of “desperation” is not going to bode well for you—and it’s not going to be much fun for the clients you’re trying to woo, either.

Everyone’s financial / lifestyle situation is different, of course. But generally speaking, my recommendation to aspiring freelancers is “don’t quit your day job” until you feel confident that you’ve built up enough of a freelance clientele to support yourself without one.

Imagine chatting with a potential freelance client, making conversation gracefully and joyfully, knowing that regardless of whether they hire you or not, you’ll be fine? That’s a beautiful space to operate from, and ironically, you’ll wind up with more clients if you take that kind of “no stress, pressure-free” approach. So, if possible, try to operate from that place. If that means keeping a part time or full time job for a while longer, to help get into the right emotional space, why not give yourself that gift?

Look at it this way: if having a job helps you feel relaxed about money, so that you can market yourself to freelance clients gracefully and calmly, then your job is a huge check in the “plus” column. It’s not holding you back—it’s helping you!

If you’re going to leap into freelancing, LOPIS, I advise you to make the leap with a happy heart, some savings in the bank to fall back on, if possible, and the confidence of knowing that you’ve already got a small coterie of people who are interested in hiring you. This will give you a self-assured, peaceful attitude… and that attitude will make all the difference.


Ellen says:

I have been a freelancer most of my life and I must say- I wouldn’t have it any other way. I love the independence, the fact that I am my own boss, and the creative opportunities.

While there are lots of benefits to freelancing, I agree with Alex that it is really important to be financially stable before diving into the freelance world. There is no fun in waking up in a state of panic every day. Make sure you do a budget and figure out all your expenses. Remember you will be paying for everything- including health insurance and self-employment tax- so budget for all of it.

There are also other things to consider before becoming a freelancer. Here are just a few:

Do you have a marketable skill?
In other words are you offering something that people need and that they are willing to pay for. You can have all the passion in the world- but unless you are filling a need, you will not create a financially successful business.

Do you have a large network?
Freelancers who are well connected tend to do the best, financially. But don’t despair if your network is not yet robust. You can begin to build it slowly through social media and also by networking. Go to events in your community. Put yourself out there. Offer free workshops; write articles in the local paper. If you are selling an actual product, get a booth at a Farmer’s Market. There are so many ways to grow your network. It’s just a matter of doing it!

Which leads us to the next important factor.

Do you have the right temperament?
Freelancers need to be self-motivated, comfortable working with many types of people, and open to networking and hustling to get jobs. You won’t get work if you hide in your house all day.

We know this sounds like a LOT to think about. And it is. But in the end, if being a freelancer suits your personality, it is well worth all the hard work.

Good luck!

We’re excited for you, LOPIS as you move to your new town and begin a new chapter of your career.

Let us know how it goes!

Alex & Ellen


Image: Willie Franklin.