“Hacking” Your Way to Freelance Success?

Ed Gandia here, taking over the reins at The Writer’s Life this week.

Here’s something I’ve learned since I decided to become a freelance writer in 2003.

The idea of freelancing for a living is a bold move for many people.

In fact, even when we have a burning desire to go solo, becoming self-employed seems so daring and unnatural that it often creates a number of dangerous, self-imposed obstacles.

I’m talking about nagging fears and doubts that, if left to fester, can stifle your progress.

Because of that, many aspiring freelancers don’t ever get started. Sure, they plan, study and get ready. But they don’t execute!

So, unless you’re naturally self-confident in everything you do, I’ve found that you often have to “hack” your way to a successful freelance business.

In other words, you have to trick yourself into doing a bunch of small, slightly scary things gradually — each building on the other — until you finally reach your destination.

After going through this process myself and helping other new freelancers do the same, I’ve discovered five proven hacks that will give you the courage and momentum you need to launch a successful freelance writing business.

Fortunately, these are simple and very “doable” hacks you can start implementing right away. I’m going to share all five of them with you this week. Start applying them immediately, and I bet you’ll experience a significant breakthrough by Friday.

Ready? OK, here’s the first hack …

If you have a day job, start your writing business on the side.

Michael Masterson calls this “chicken entrepreneurship.” Sure, it’s not the sexiest approach. But, if leaving your job today is either financially unfeasible or just feels way too scary, this is the way to go!

I know it works, because this is exactly how I launched my freelance business. And after 27 months of working my business on the side, I had enough clients to quit my day job.

Chicken entrepreneurship enables you to lay the foundation for your business without the added pressure of having to bring cash in the door immediately. It’s also a great way to get out of a dead-end job without sacrificing your paycheck or putting your family in financial risk.

Fortunately, the technology to do this seamlessly has never been better. You can put up an amazing-looking Wordpress website in no time. And you can have your clients’ emails go straight to your smart phone. That way you can get back to them during breaks or your lunch hour.

Sure, it might take you longer to grow your business this way. And you’ll have to find pockets of time during nights and weekends to do your work and to prospect for clients. (That means cutting out some TV time and learning how to become more productive.)

But if you’re disciplined and determined, this is one of the safest and most realistic ways to build your freelance business. It’s perfect for those of us who tend to wait until the stars align perfectly before taking action.

Have you tried launching your business on the side? If so, what have you found works best for you? And if you haven’t, what’s keeping you from getting started?

I’d love to hear from you. Please share your thoughts in the comments area.

Tomorrow I’ll share the second hack that enabled me to achieve fast results early in my freelance career.

It’s something anyone can do … yet I’m always amazed that few new freelancers ever try it.

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Published: June 16, 2014

36 Responses to ““Hacking” Your Way to Freelance Success?”

  1. I have a writer website, updated LinkedIn profile and several AWAI programs under my belt and am ready to start marketing to get my first B2B client. It seems like it is taking longer than some people that I read about but I have to remind myself that I am freelancing on the side. Looking forward to the rest of your 'hacking' tips.

    Sandra KnightJune 16, 2014 at 3:04 pm

  2. Hi Ed. I write content through a couple different agencies while working full time - this means every night and weekends are devoted to writing articles and I'd be interested in learning how to move forward - create a killer website, etc. to eventually write full-time. Thanks for sharing your inspiring story/tips.


    Guest (Tracy R)June 16, 2014 at 4:14 pm

  3. I have a full-time 9-5 job, and I've been working part-time for about a year on oDesk dot com. It's been a good source of extra money, but I'm a long ways from being able to quit my day job. Looking forward to the rest of your tips to "hack" my way to freelance success.

    Guest (Evan Jensen)June 16, 2014 at 4:46 pm

  4. Great article! I've been chicken-freelancing in a different way, as a FT stay-at-home mom to a one-year old who's not a great napper (myth, you can work while your baby naps!). All my business has come via referrals, and I've been nervous to put up a website. Mostly because I wasn't sure how prospects would handle not having their inquiries answered right away, but I guess that's the way it is for anyone with a side business. Your perspective helped a lot, thank you!

    KristenBJune 16, 2014 at 5:38 pm

  5. I am just getting started as a freelancer. I am developing my new business "on the side". You mentioned 1. it would take longer, 2. To be disciplined & 3. To be determined. Great suggestions! And to apply all that we need to be balanced. We need to recognize the priorities, for instance, the job providing the income gets priority. We need to be realistic in the time we can devote to the new career & not jeopardize the income job. I believe being balanced will keep resentment from creeping in, too. Being balanced also will help with patience as it all works out! This is what is working for me. Looking forward to your other "hacks"!

    CarrieBJune 16, 2014 at 5:42 pm

  6. Hi Ed, I think Michael is right on target with the phrase, "chicken entrepreneurship." The majority of us new copywriters have too many financial obligations, especially when you are supporting a family. If someone was single with no commitments, then it could be a different story. The important thing is to make those connections and build that presence so that you can be seen. I know that you are a web expert, and I realize that it is vital to make yourself know with a quality website. I am blogging right now, but my website will be coming up soon. Thanks for the tips, and I will be looking forward to your next ones... Jimmy

    Guest (jimmy bradburn)June 16, 2014 at 6:17 pm

  7. Always encouraging to see how someone else made the move. I'm still working through the Accelerated program and lost momentum a couple times. But I'm "back in the saddle," committed to completing the program and reading all I can about copywriting.

    My problem is money...the lack of it! My current job is "feast or famine," working too much or not not enough. Quite aggravating, but motivational.

    I'll give up hosting a weekly open mic to do this properly and narrow my focus. A lot.

    Guest (Garth Osborn)June 16, 2014 at 8:19 pm

  8. Ed, I am quite encouraged by your comments on freelancing. I look forward to tomorrow's iteration.
    Sincerely, Ben

    Guest (Ben)June 16, 2014 at 8:27 pm

  9. Ed, You read my mind! I've recently joined AWI and PWA taking off "out-the-gate" with a fervor. Life has recently gotten tougher and now I'm wondering if I indeed have time to do this.

    Your example of progress taking some time is indeed reassuring.

    John KeyserJune 16, 2014 at 8:43 pm

  10. Hello Ed,I have joined the AWAI accelerated program for copywriting,few days ago. Just wanted to know whether I could work from India for global clients and get paid in dollars? Or will I be limited to only Indian clients? Thanks for the inspiration to go ahead..

    Anil AbrahamJune 16, 2014 at 9:51 pm

  11. Hi! Ed, Thanks for sharing your enriching experience. I recently joined AWAI, for an entirely different purpose-to improve my writing skill. I have a blockspot where I share my "Lessons from Life". I am a free-lancer and took retirement from job at the age of 40 years in 2008

    Guest (Jitendra)June 16, 2014 at 10:02 pm

  12. Hi Ed. I'm in the middle of launching my writing business, and I've slowly dwindled my time at my job to just 20 hours a week. It's been a great transition.

    I attribute this transition to two things:
    (1) Constant updates with my employer
    (2) Creating and executing a very specific schedule for the writing business while I'm at home.

    I post the schedule right above my desk, and stick to it. I'm even a stay-at-home dad, and although that makes it a bit more tricky, it can be done!

    WesleyJune 16, 2014 at 10:28 pm

  13. Hello Ed, and thanks for your efforts on my behalf. First of all you should know that I am only about half way through the accelerated Copywriter Program and have yet to write the first restaurant letter. I go blank every time I look at it. I actually came out of retirement to do this and I will do it successfully sooner or later, but I have to get past the restaurant letter. Someone mentioned that there were 37 programs that we could be asked to do and I am having trouble getting past the easiest but I will!

    Guest (Bob Thrall)June 17, 2014 at 9:02 am

  14. I've been so scared of trying this that I was scared to even start the learning process. I'm happy to say that not only have I started working on the programs that I purchased, I have a plan for a niche to begin with. As a matter of fact, I had to come up with the idea for the niche before I could get myself to start working on the programs. It made it seem more real.

    Guest (Elaineb)June 17, 2014 at 10:52 am

  15. Great start with the article Ed…I'm looking forward to "hacking" my way out of the cubicle confine.

    I'm moving slowly forward in the direction of my copywriting goals - each day I feel I'm getting closer. I get up early in the morning to spend at least 45 minutes on writing/learning.

    The one thing I find hard to do is "switch channels" after getting home from work.

    Guest (Jeff Melvin)June 17, 2014 at 2:08 pm

  16. Hi Ed, As usual you are very helpful. I was doing just what you suggested when I found myself in a life crisis. My husband of 30 years and I divorced. I no longer worked in the "family business" so I had to fast track my writing/publishing career. My alimony will end on 1/2016. Talk about feet to the flame. Walking into a new entrepreneurship is like wading into an icy lake, one step at a time. Take advantage of having a job for as long as you can. When you're ready dive in it warms fast! Marie

    Guest (Marie)June 17, 2014 at 5:39 pm

  17. Hi Ed, how do I manage to start my own business as freelance writer, with my web site, blog, promoting and networking in social media channels, etc. and at the same time being unnoticed to my actual employer?.

    He wouldn´t like to know that I am working for other companies.
    On the other hand I find it difficult to engage with new customers if they don´t see who is behind. Thank you.

    Guest (Luis)June 18, 2014 at 6:19 am

  18. Hi Ed, I've been freelancing for a while, this is a difficult path. But now I'm powered by AWAI. I hope this will work great.

    CecalliJune 18, 2014 at 1:38 pm

  19. Hi Ed!, Liked your approach of responding to individual comments.

    JitendraJune 19, 2014 at 3:47 am

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