My Interview with Jason Ianonne

This entry is a special one. It’s my interview with Jason Iannone. He’s a great friend of mine and my former roommate. He works in his jammies as much as he wants and loves what he does! I am happy to say that he’s done very well for himself and has an amazing work ethic!

Sit back and enjoy this great interview where Jason shares his history and some great tips if YOU want to work in your jammies too!

How long have you been working from home/What do you do?

I’ve been working from home since June 2010 part-time. I became a FT home-worker January 2013. I’m a staff writer for various websites under the Zergnet label.

What was your biggest motivation for wanting to work from home?

I’ve long known I was a good writer and loved the idea of making money off of it. I was struggling in a retail job and wanted out, plus having a young son meant if I could make some extra money while staying with him, all the better. Later on, it simply became a case of not wanting to deal with demanding customers any longer.

 How did you get your first gig?

I cold-emailed the editor of a pop-culture website called WeirdWorm, asking about work. He asked me to send him an audition piece, he loved it, and I was in. later, I found out he had no standards and accepted literally everybody, no matter how great or terrible they were, but by then I was pitching to other, better sites anyhow.

It takes a lot of discipline to work from home. How do you balance your life and the job? What is the easiest thing to balance? The most difficult?

I’m currently expected to work 9-5, Monday through Friday, so that expectation helps 🙂 When I was freelance, I would always plan my schedule ahead of time as much as possible. If I knew what I was doing ahead of time, that made it easier to know when I could work. Basically, I had (and have) good communicators in my life, making the balance between work and life easier.

Today, even with the 9-5 schedule, it’s hardest to balance that and time with my girlfriend, since she has a teacher’s schedule and is usually home before 5. But working from means I can cheat a little and butt out of work early. I just make up the hours later.

Do you ever get lonely not being around other people on a daily basis?

Sometimes. Though I can always drive to Starbucks, Barnes & Noble, or the local library and work from there. The people there may not be my co-workers, but they’re still people, and that does help my social side. Besides that, living with my girlfriend is a great way to not feel lonely at the end of the day.

Where is your favorite out of the home place to work?

Any place with a working plug 🙂 Specifically, Starbucks if I’m feeling mainstream (they usually have some nice tunes playing as well), the library if I’m not. I’ve also started writing outside on my porch, though that might count as “home.” The Sun’s a terrible co-worker though, so I won’t do that too much until I can find a good anti-glare guard for my screen.

When you look at your current situation and how you got there, what was the defining moment that led you to take the work from home path? Do you have any regrets?

Just the realization, after several years, that I was never going to be comfortable working in retail. I could do the job itself fine, but I didn’t have the right mentality at all. Plus, as I got better and better at writing and got more regular gigs, I could no longer justify even supplementing my income with retail, and so once I knew I had enough from-home work to pay all my bills, I stayed home for good.

I have no regrets and am even trying to branch out. I have the M-F job, but I’ve also secured a book deal and am currently writing a book of fiction. The new goal is to work from home as an actual author of actual books.

Do you have any advice for those who want to work from home or freelance?

To steal from John Cena and many others, “never give up.” There’ll be times when work is slow, there’ll be times when the assignments are dry and dull, there’ll be times when you’re lonely, there’ll be times when you wonder if you can really afford to work from home. But keep going, keep working, don’t be afraid to cold-email or cold-call tons of sites about gigs (the worst they can say is no), and learn to live frugally whenever possible. Learn to cook, become an expert Goodwill shopper, and don’t buy endless “stuff” or toys you don’t really need. That way you’ll eat well, live well, and can afford to tell the retail counters and cubicles bye-bye forever.

Well, that’s it. That was my interview with Jason Iannone. Thank you, Jason, for doing this interview! I’m thrilled that you shared all your insights. To check out Jason’s other work, be sure to jump over to his website.

To see my last entry, click here.



They’re bound to happen for any freelancer. It is in these times that we need to remember how to go back to the basics of what made us want to do this great work, to begin with. For me, slow-downs mean looking at what my business can do to grow and improve. With the new year approaching, it will be a goal of mine to grow my business in 2017.

This past year has been full of ups and downs for me and my business. I started the year with a couple of clients, unfortunately, throughout the year, things happened that were not entirely in my control. Experiencing personal setbacks that made keeping my business afloat was also a theme for this year. I did not once consider abandoning my business but I did decide to take a break for a while. Giving up on something I feel strongly that I am good at was simply not an option. It takes a special person to look at slowdowns and how to work with them.

I had my roommate who is also a freelancer. He gave me great advice and is an inspiration. He kept me from giving up on something I still feel passionate about. Clients came and clients went, but sometimes I think that made things more difficult for me. As my good friend says, “the wheel turns”. This is true of freelancing as well. The new year will be one of great change and growth. Here are a few goals to keep in mind when business slows down:

How to Handle Slowdowns:

  • To pitch at least 5 times a week
  • Work on gaining one new client a month
  • Continue to balance your work and freelance life with everything else
  • Remember, you started this journey for a reason
  • Above all, take each slow down or setback as a way to grow

Keep this in mind, my freelance friends, when you get slowdowns in your business, use them to your advantage. Grow and learn from them the best way you know how and don’t give up!

Click the link to read about My Journey to Working from Home.

My Journey to Working From Home

My journey to working from home is just beginning.

***This post contains affiliate links

Right now, I work a regular 9-5 job and it’s eating me alive. A few years back, I decided to start freelance writing as a side hustle. It became something I enjoyed doing but keeping clients coming back was not always easy.

Over the last few years, I’ve realized that not only am I not a “cubicle guy” but also that I truly enjoy the idea of working from home. Unfortunately, my current position doesn’t allow for that. This makes it very tough to enjoy what I’m doing on a daily basis. My mom works from home and I’m so jealous!

When I first thought about working from home, I wasn’t sure what I was interested in doing. I’d had a few jobs of course but what skills did I have? Well, it turns out, I have a ton of great skills! I have 10 years in Customer Service, I can write well (one reason I started this new venture), and I connect with people. Is that enough? I would say yes it is. The next thing to do was to test the waters.

I actually started working from home as a freelance writer. Of course, I was also working my office job too so I had to balance the two. For a while, I was able to and then I took on a client that I grossly overestimated myself. Why am I telling you this? It’s simple. I’m telling you all this because it’s the truth and also something that can happen to even the most seasoned work at home maven. I’m by no means a maven but my journey to working from home is just beginning.

It took me a long time to realize that my happy place was outside the office. I feel most comfortable in my own apartment (as most people do) and there have been numerous studies that say people work better from home if they have the discipline and ability to do so. In fact, there was a Forbes article recently that talks about this trend in a balanced way. Here’s another Forbes article from 2016 that addresses this trend further.

One of the best ways to start the journey is to first, ask yourself the question what you’re passionate about. Is it sales? Is it Customer Service? Do you have a knack for writing? Once you’ve asked yourself this question and hopefully gotten an answer from yourself, you can start thinking of ways you can use that to start working from home. A word of caution, I do not recommend just quitting your job at this point for obvious reasons. I would say have at least 3-6 months of money saved up before you jump your 9-5 ship. Some people may need even more than that. The point is, save before you bail!

Here is a list of things I would recommend doing once you figure out if working from home is good for you. These can be done in no particular order but I do recommend the first four bullets be done quickly and in order if you can.

  • Talk to your friends and family about your decision
  • Figure out a game plan
  • Look at your bills
  • Look at your current household income
  • Start saving, even more, each month
  • Brainstorm ideas if it goes south (sometimes it does)
  • Don’t burn an employment bridge
  • Start setting up your business plan
  • Maybe set up your website:
    • for a quick rundown of how I set mine up through ***SiteGround click here
  • Find great Facebook groups to join. There are tons of them so have fun searching and network like crazy!
  • Start researching potential clients and sending out some cold pitches. (Believe me, you send out 100 you will get a few back).

When I made my decision to start my journey to working from home, I knew it was not going to be easy. I have a ton of things to do. I’m also acutely aware that not every month or even day is going to be better than my office job. The truth is, if that was the case it would be VERY boring. One of the first goals that I had was to set up my website(s). Now that I’ve done that, I can take the next step because I’ve also completed almost everything else on that list above. The one that I need to work on is saving money.

As you begin to think about if you can pursue work in your jammies, take stock of all the skills you have and how you can use them to potentially make even more money than at your 9-5 job! I’m not saying it’ll be easy, but what I am saying is that you can do it! When you start your journey, and I hope you will, go for it and have the passion to go after your dreams just like I’ve started to do with my journey to working from home.

Bottom line is, it’s a matter of perspective. My journey to working from home is just beginning and yours can too! Have a little faith in yourself, share your passions with those you love, and above all take a leap of faith. After all, you never know what can happen when you believe in yourself! Until next time, keep living your dream and eventually, you will live your dreams!

Last week’s entry is up! Click here to read about Transcription from Home.