The Ups & Downs Of Freelancing (Working Day & Night)

Most of my adult life has been spent working for other people. Even when I achieved a leadership position, it was still under the umbrella of The Company.


 I did go rogue back in 2013 and went to work for an online paper. I was so happy to be writing and editing and helping train other writers. This is my dream job. If I could get paid well for writing, I would be in a permanent state of bliss. Unfortunately, I was not making the money I needed to support my family.

I was severely depressed for several weeks after I left that job.

I mentioned in another post that as an independent contractor or freelancer unless you get a spectacular client that pays extraordinarily well, you might need more than one gig to cover everything.

I didn’t understand this in 2013, but the lesson stayed with me.

Down to #WageLife

Thankfully I picked up another #WageLife gig in early 2014. That one lasted until 2016 when I lost my childcare and had to miss work “too much”. I was released on what I thought were good terms, but each time I have reapplied to that company, I was declined.

The entire time, I was still looking for some kind of #WAHLife gig to replace that JOB (Just Over Broke) so I could get about the business of raising my child without moving us to a cardboard box.

Let The Juggling Begin

In September 2016, just after I was so politely fired (#notsalty), I started looking at Uber and Lyft. I had already spoken to a Lyft driver who had good things to say about it. Even though I didn’t have a car, Uber and Lyft both had a program where you could lease a car from them and start driving right away.

They took the cost of the lease out of your earnings automatically, so there was no extraneous expense, aside from gas. They even covered upkeep like oil changes and other maintenance.

I started the process of leasing a car from Uber. When I had the money for the $250 deposit, I caught a Lyft to a local lot and had a look. I wanted an SUV, but they only had sedans. I ended up with a lovely 2015 Toyota Camry.

Despite my aversion to being out of my house for extended periods of time, I started working right away. I had to make sure I made enough to cover Uber’s $180.00 weekly lease as well as my bills.

Shortly after I started with Uber, I added Lyft to maximize my driving time. When one was slow, I switched to the other platform.

I had a rider who mentioned another company in my area called Favor They are a delivery service that started in Austin, TX. I was not always comfortable having people in the car with me, but I had to pay that weekly lease to Uber.

*Favor is only active in Texas

I added Favor to my list of freelance gigs I was running, and the income got somewhat better.

The Cost of Doing Business

In 2017 I got a pretty good income tax return, so I decided it was time to ditch the lease. I went back to the same car lot and picked up my Ford Explorer. It was older (2008) and it did not have the awesome touch screen from the Camry. It did have Bluetooth and voice capability, so I went with it.

It was also about $400 cheaper than my Uber lease by the month. Overall, I was paying over $700 a month to lease the Camry. With the Ford, my monthly outlay dropped to $270.00 + insurance at $160.00. I was still coming out way ahead.

Crossing Over

I ran with Favor for a good while. I liked having my car to myself and the deliveries weren’t too bad either. I got to know the restaurants in my area pretty well, and when I did Uber/Lyft, I was able to enhance my riders’ experience by sharing my eatery knowledge with them.

While I was doing all of this, I had another work from home job reviewing ads and videos for a company called ZeroChaos. It paid $15.00 an hour, weekly by direct deposit and that was a pretty good gig.

Unfortunately, it was limited to no more than 25 hours a week. That contract ended in July 2016, which is one of the downsides of contractor work.

Not only do you have not much chance of benefits but you also never know exactly when that cash cow is going to dry up. We were notified by email 2 days before the end of the ZC gig.

How Many Jobs??

Talking to people about my various gigs usually elicited the same reaction: How did I balance it all? I have to say that my home life suffered.

I was rarely home to cook dinner, so my son had to pick up that slack for me. Being a teenager, he often threw together a meal that was not quite what I would have done. I had to remind him to do a veggie and to cook to everyone’s tastes, not just his own.

My husband was doing laundry, and his shirts were never ironed. My house cleaning fell way behind. It wasn’t filthy, but not as tidy as I would like to keep it.

The very worst part was I was missing out on my baby boy. He is now 4 and I am not doing any of these gigs at the moment. I am determined to find something steady and lucrative that I can do from home, with him dashing about as he does.

This is the challenge for anyone wanting to work from home, at home, virtually or remotely as a telecommuter, freelancer or independent contractor. We are all trying to strike that balance of work-life. Making enough money to cover living expenses and to live well are the ultimate goals.

Time On My Side (And Front…And Back)

The scheduling flexibility available when driving for Uber, Lyft or Favor is excellent. I could work in blocks of a few hours at a time or take one call and take a break. I could log out, go have dinner with hubby, and go back to work or go home.

It always requires discipline. Nobody is going to call you to ask why you’re not working. It is completely up to you to motivate yourself to get up and get out the door. You and only you decide how long you’re going to work, how many calls you’re going to accept or reject. With these gigs, you have almost complete control of just how much money you make.

Win…And Go Home!

That discipline also comes into play when deciding when to go home. Uber implemented a change to its platform that would not allow drivers to work more than 12 hours at a stretch. This was for safety reasons. If you hit the threshold, your Uber driver app would not allow you to log back in for work for 6 hours. This was to force drivers to rest.

A lot of people only drive on the weekend, from Thursday through Sunday. They slept in the car and pulled 12 to 16 hours of driving without a break. These people made mad bank, of course, but they traded this for safety.

Sleep deprivation diminishes reaction time and attention span. When you drive for a living, this is not a good thing. Personally, I got woozy anywhere from 4-6 hours on the road. It is not really seen as strenuous work outside of the industry. Anyone who drives for a living can tell you that physical and mental fatigue can set in before you know it.

Oh Yeah…

While I was doing all this driving, I was also working from home for SigTrack. It is a data entry gig confirming voter registration information. It is penny work, but it goes pretty quickly.

It wasn’t very hard to do enough work to get a small check. The most I ever made in one pay period was $50.00. It paid weekly, however, so it was good pocket change.

I am still registered with them, but I have been focusing on Appen.

I picked up Appen shortly after I started with Allied (and I was still driving, mind you). With Appen, you are assigned to various projects. The work involves anything from tagging videos and ads to recording voice prompts to improve voice recognition software.

The pay is usually around $10.00 an hour, but I have seen projects paying as much as $19.50 for specialized work. The pay periods are usually monthly, but I am starting a project soon that pays biweekly. This one is transcription work and I am looking forward to it.

Other Side Side-Gigs I was running at the time included:

Secret Shopping for:


Second 2 None

Shift Smart *

And photo inspection for insurance claims with Onsource. If you decide to check Onsource out, please use my Inspector ID in the referrer spot. It is 35852.

*ShiftSmart is completely app based. All of these gigs require a mobile phone and the app to work them. Onsource requires verification of your driving record.

I was a busy bee.

And Then…

In 2016 I started classes at Everglades University Online. I have been interested in herbs and natural healing all of my life. When I saw they offered course for a degree in Complementary & Alternative Medicine, I went for it.

I’m still attending but had to take a short break. I’m adding lessons at The Herbal Academy, because why not?

Last But Far From Least

Remember when I mentioned earlier that I was on the hunt for a #WAHLife gig? I found Wealthy Affiliate in 2014 just after I gave birth to my now 4-year-old son. At the time I was struggling with having to back to work in 4 weeks instead of 6. I used 2 weeks due to my mother’s illness at the time.

I can only speculate on why I didn’t get into WA at the time, but I guess it’s a combination of factors.

Anyway, I found it again earlier this year. After 3 months I own 2 domains and 5 websites. This is one of them.

I won’t get into everything they offer here, but I wrote a review on them. Let me remind you that I have been searching for some kind of legit work from home gig for over 20 years. This is the first and only platform I can say all these things about:

  • It’s not a scam.
  • Has ongoing, relevant & timely training.
  • A responsive and helpful community. No competing for customers or commissions.
  • Affordable!

Even on my How-Are-We-Going-To-Pay-That budget, I can afford it.

Take a look. Your first 7 days include free access to select Premium features. If you upgrade within that time, you pay only $19.00. After that, it is only $49.00 a month*.

*Via auto draft. No refunds. Cancel any time.

One More Thing

If you do decide to go Premium within the first 7 days, send me a Private Message or drop a note on my profile page. I will be delighted to give you these BONUSES:

• Unlimited access to ME as your Mentor.

• Feedback on your content and your website. We’ll cover everything from syntax to social media!

• Access to the Diamond Traffic Program to boost your site.


As you can see, living the #WAHLife as a freelancer or independent contractor has its challenges, I can honestly say I don’t get bored. I do get tired, but I expect that. Nothing worth doing is easy.

While working on this, I was reminded of a popular skit from a mid-90s TV show called In Living Color. It was about a family that worked several jobs to make ends meet. I hope you enjoy this little snippet as much as I do.

Until next time,

Gig on.

Gwendolyn J

19 thoughts on “The Ups & Downs Of Freelancing (Working Day & Night)

  1. I am at awe of your ability to switch among so many different things! My husband had driven Uber using our family car for about a year. Even though the car was paid off, with the gas expense, car depreciation, his time away from home and sleep deprivation (he worked his day job as well), we’ve decided that it wasn’t worth it.

    Besides your endless energy, you seem to have an amazing set of skills and a variety of interest. Managing 5 websites simultaneously requires incredible ability, but with the love for writing you mentioned, I understand that it’s very much possible. I hope that at least one of your websites is related to your other interest in herbs.

    Thank you for sharing your experience with all the ups & downs of freelancing. I know that I couldn’t do many different things at once. I guess it’s a matter of personalities and skill set and that’s the difference between freelancers and business owners.

    With your energy, you should be a millionaire by now! Aren’t you thinking about shifting from a freelancer towards a business owner? You must be… since you are with Wealthy Affiliate now and working on your own online business. Based on what I just read about you, I have a valuable yet free opportunity in mind for you, which could work well with what you are already doing at Wealthy Affiliate (email me if you are interested to hear about it).

    Wishing you great success in everything you do, and please take good care of yourself. 

    ~ Julia

    1. Julia,

      One of the reasons I’m not doing that whirlwind anymore is because I got burned out. That was my life for about 2 years.

      I just recently found WA and I am very happy with it. It has given me insight and purpose. I am the freelancer gigs right now because I have to have some income, of course. But even that has been a dry river bed lately. 

      If your opp is paying me to work on something, I will look at it. I haven’t had a paycheck over 50 bux in nearly 2 months so, anything more lucrative than that is welcome. 

      Thanks for stopping by 🙂

      Gwendolyn J

  2. I kinda feel like I was reading about myself but in a different and similar way. I used to an entertainer and when I had to retire from the stage due to a life-changing operation I felt lost and tried a few different things, all of which I was very good at but not happy and then I too found Wealthy Affiliate and a year later, I am making money and loving my new online life and Wealthy Affiliate gives you absolutely everything for anyone to become successful.

    All you have to do is learn and build as much as possible and have awesome goals to work towards and a really amazing WHY and you will find success.

    Awesome post 

    1. Vicki,

      Thanks so much!

      I decided to drop all those gigs and stay home and work a few months ago. I like being home to have dinner with my family -a dinner I actually cooked. I like being home to put my baby boy to bed and being here to feed him breakfast.

      I’m not making much money yet, but I am working on it. #WAHLife is the goal. I want to set my bills on autopay and never worry about the money being there. I want to be able to help my kids with whatever they need and not worry about how hurting my own finances doing it.

      I have all the tools I need to make these dreams come true :).

      Thanks for stopping by!

      Gwendolyn J

  3. Oh my goodness what busy little bee!. Gotta say kudos for the determination and getting through it all. I love that you have highlighted how one can optimise their driving opportunities by working with a variety of companies.

    1. Derek,

      A lot of people drive both Uber & Lyft because when one is slow the other tends to pick up. Fortunately, as contractors, we are not beholden to either company so we are free to work for other platforms of the same or similar type.

      I’m taking a break from all of that right now, but I may pick it back up. SUmmer is a slower season but with events and such upcoming you can slide into some good money.

      Thanks for stopping by,

      Gwendolyn J

  4. You are a wonder woman! I never skip a single word as I read your blog. You inspired me to keep working for my kids. I am not sure if I made the right decision to switch in online business because I don’t really know much about this. I am frustrated with how things are going but we have to keep going, right? I also tried Appen but due to some reasons, I didn’t get the access. Online side jobs aren’t easy for non US or UK residents. We have very limited and available apps or programs for this that’s why I’m having a hard time. We do have locally available apps but it really doesn’t pay much.

    I joined WA, it was great but I get intimidated with sites that I comment everytime I read about tools you need to pay to get good landing, etc. Thanks to you, I found encouragement. More power to you!

    1. MIssus B,

      A lot of those apps that ask you to upgrade to Pro on your site you don’t really need to. I’m using Jaaxy Lite, the free SEO All in One, the basic Pretty Links, etc. 

      I don’t even pay for an autoresponder right now. When I get to where I have steady, growing income, I will consider upgrading Jaaxy, but the rest… meh not really. I get what I need from them.

      Don’t be intimidated, you are a superwoman too! You are at WA, you are making your way. We are all on different paths to success. 

      Keep going!

      Thank you for stopping back by 🙂

      Gwendolyn J

  5. You worked so many different places — how did you remember where you were going next?

    I worked for a couple of years for temp agencies in Seattle.  It seemed like the best jobs were the ones that were completed the soonest.  Have you discovered some places with temp jobs have better offers than others?  Can you always find enough to keep you working?

    I just researched a company called Fiverr that is a freelancer website.  When you apply, you can either hire someone for something or you can offer your services.  Have you ever looked into Fiverr?

    I am glad you found something that should end up making your life a little easier. It sounds like an excellent choice.  I will look at it, too.  Good luck on this newest venture.

    1. Fran,

      The secret shopping and insurance inspections were spot work. I didn’t do those daily, just 2-3 a week on average. 

      The driving was a little more complicated. I would jump into one and if I got nothing within say 30 minutes I’d jump into the other, and so on. 

      The data entry I did from home, on days when the weather was bad or I just didn’t want to drive. And I did school every night after all the madness was over. 

      Now I am staying home and doing Appen, writing gigs, and working on my Wealthy Affiliate sites. 

      So things are a lot calmer now :).

      Thanks for stopping by,

      Gwendolyn J

  6. This article reminds me of myself when i just started online.. 

    I signed up for a few different websites. was really trying to make a buck here and there.. it was rough to be honest..

    I signed up for appen a few months a back but haven’t really done any of the assigned tasks,..

    was great reading this article knowing others have ups and downs too and that no one is exception. 

    1. Michael,

      I would encourage you to take another look at Appen. I agree the work can be spotty, but when it is available, it is timely pay. 

      And they do try to roll you into another project if one ends. 

      The madness has calmed down quite a bit lately. I have taken a break from driving for a while. I’m staying home to tend my family and work on continuing my herbal education.

      Thanks for stopping by. Let me know if you want to discuss any other gigs out there. 

      Gwendolyn J

  7. Wow Gwendolyn!  How you keep juggling so many things at one time is amazing to me.  Your article was captivating, enough so that I read it in it’s entirety.  And for me that is saying something!  I was not aware of the lease options with Uber and found that fascinating.  What a great motivation to keep people working.  

    But I was drawn more to the mention of Wealthy Affiliate near the conclusion of your article.  It sounds like you are dedicated to achieve success and who wouldn’t want you for a mentor.  I’ve been looking for something that I can do from home but I don’t have that much experience with websites.  Is there training on this subject?



    1. Mike,

      The training at Wealthy Affiliate takes you from choosing a niche to building your site to adding relevant content. You learn how to get ranked on search engines which generate organic traffic which can build into revenue. 

      It is very thorough but delivered in bite-sized chunks you complete at your own pace. 

      Here’s a link to check into it further. Let me know if you decide to give it a try. I will be happy to assist you.

      Thanks for stopping by 🙂

      Gwendolyn J

  8. Oh Wow! I was glued to your blog. How in the world did you manage all of that responsibility! I always wondered about Uber drivers. Your personal experiences here are very enlighting. I had no idea people slept in their cars to work 12-hour shifts. How much does Uber pay per hour? I like that you can schedule out blocks of time. The delivery job also sounds interesting but I live in Michigan, not Texas. I really enjoyed your blog here. Thanks!

    1. Anne,

      Uber does not have employees, they have contractors, so there is no”hourly” pay rate.
      There are days when you can net around $20 an hour average (after gas, food, etc) and days where you will barely make enough to cover your gas and food for the day.
      Like a lot of IC gigs, it can be feast or famine.
      This is why I added Lyft & Favor, to fill those famine days with some productive, revenue producing activity.

      Thanks for stopping by,

      Gwendolyn J

  9. Hi Gwendolyn ,
    Excellent article on The Ups & Downs Of Freelancing , very useful and valuable information to me , as I am also starting my ways to be a freelancer , I am doing various of jobs online , it is hard but I am doing my best , I agree with you on Wealthy Affiliate , it is excellent , I just signed up recently and started my course , it’s definitely not any kind of scam , it’s a great training program that I hope will help me , and all of us , definitely recommended !
    Thank you for this interesting post !
    Best Regards,

    1. Alex,

      Be careful to independently track your hours. I have had to remind some about my time occasionally.
      You may want to create a folder on your computer called WORK and make separate folders for each gig. I save hours, pay rate, SCope of Work, Guidelines, and check stubs (digital) for each gig.
      It’s very useful at tax time to have all of that handy.

      Also, keep receipts for anything you pay for that is used in your work. This includes internet costs, office supplies, ordering pizza, stamps to send forms, paper & ink for the printer, any software you buy to facilitate your work, etc.

      In some cases, you can even include part of your power bill, rent & cell phone. ONe year I claimed my satellite service because I was a sports writer and I needed the Sunday Ticket to watch games out of my area.

      Consult a tax pro to make sure you keep everything sorted :).

      By the way, I beleive we may even be able to claim the cost of WA as a business expense ;).

      Thanks for stopping by,
      Gwendolyn J

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