"In the end, we only regret the chances we didn’t take."

1,000 Trivia Questions And 1 Great Review

A few days ago I mentioned that I secured my first contract through UpWork.  So, I figured it would be as good a time as any to talk about it.  When Josh and I first started talking about our five year plan, I knew that “not working” wasn’t going to do it for me.  I’m too high-strung and like to be busy too much to not have ANY work to do.  The opportunity to make money is always a good thing, too!  But, when I leave my current job in 2021, I’m not sure that I really want be tied to a traditional, 9 – 5 (or o’dark hundred – the earliest I can possibly leave work) job.  Unfortunately, my skills on paper look pretty weak.  I’ve got experience in accounting but I don’t have a degree in accounting.  I’ve got experience in drug and alcohol treatment but I don’t have an official certification.  I’ve got experience in the criminal justice system but I don’t have a Masters Degree, which seems like the going rate of somewhat comparable jobs outside of PA.  But, I’m a hard worker, a perfectionist, an overachiever, an organizational nut and a fast learner.  So, I was / am fairly optimistic about my chances of being able to find work, but, I’m not wild about the idea of just relying on my chances to find work without a pretty stable back-up plan in case of the odds not being in my favor.  I heard about this UpWork thing and decided to check it out to see if it might be an option.

Here’s the skinny on UpWork: it’s a legal, legitimate enterprise that pretty closely resembles a prostitution ring.  (Did I mention I get paid to counsel criminals every day?) UpWork connects clients with service providers and then takes a portion of the money paid for services rendered.  It’s a platform to get connected with clients that are looking to have work completed remotely that you, as an independent contractor, can complete.  From bookkeeping, data entry and web development to transcription, being a virtual assistant and proofreading publications.  If it can be done remotely, outside of a brick-and-mortar office, there’s an opportunity to make money doing it on UpWork.  UpWork being the middle-man means that there’s a better chance that you will actually get paid for services rendered, and, if you don’t get paid, UpWork can help mediate the situation.  You sign up for an account and set up a profile, displaying your skills and interests.  As you complete work and get paid, your clients can rate the work you’ve done and let feedback about their interaction with you.  So the story goes, the better your profile (with more jobs completed, client ratings and feedback), the more likely you are to be awarded contracts you bid for.  Thinking ahead…it would probably not be a bad idea to get some work history and ratings under my UpWork profile belt now, while I have a stable job and am not relying on potentially making a living through UpWork.  That way, down the road, I have a strong profile of work history that may assist me in landing better contracts (for more money!) if we need money in a pinch (or if I decided to become a full-time independent contractor instead of returning to some type of more traditional workforce).  Kinda solid planning for eventually not having a plan, right?

So, I signed up for an account back at the end of July.  But, of course, the bureaucratic red-tape-reliant dictatorship agency that I currently work for wants to control absolutely every aspect of my life required that I submit an “appropriately completed request for supplemental employment” before I would be “permitted” to begin working any additional job.  And, of course, the request had to be reviewed.  Reviewed by my supervisor.  Reviewed by my supervisor’s supervisor.  Reviewed by the supervisor of my supervisor’s supervisor.  Reviewed by the director of the bureau I work for, a clerk in Human Resources, a supervisor in Human Resources, the Executive Deputy Secretary of the bureau I work for, an attorney in the legal department and then the Commonwealth’s Office of Administration.  (Just in case your a “numbers” person, that was 9 reviews.)  Oh, and then, it also had to come back down the “chain of command” the exact same way it went up so that everyone would know the result of the 9 reviews.  (For those keeping track, we’re up to 18.)  I concluded that approximately two months later, an act of God must have occurred as I received “permission” to begin my supplemental employment, which, just for the record, is completely unrelated to my full-time job, employer or profession.  Suffice to say, the tax-payer dollars that must have been invested in the two month approval process of my request were obviously ridiculously well spent.

There are a TON of contracts available on UpWork and requesting the contract is pretty easy.  A click of the “submit proposal” button and a few words to the prospective client about why  you’d be a rockstar working for them and you’re on your way to earning money.  Then you wait.  The client does whatever they do on their end to select the candidate(s) they want to hire (I’m pretty sure most of them shake the Magic 8 Ball) and, if you’re the lucky contestant, they offer to hire you, based on an agreement of work to be done in exchange for a set amount of pay.  I submitted proposals for a handful of contracts but had a few clients reject my proposal due to my non-existent work history on UpWork.  I submitted a proposal for a contract that I thought sounded pretty cool – finding or writing 1,000 trivia questions for $100.  (Wait…I can get paid for doing this type of stuff?!)  I submitted a proposal and, to my surprise, the client took a chance in hiring me!  The client requested that I submit my first 200 questions to him by 1/15/2017 so he could review my work and make sure everything was as he wanted it.  I submitted all 1,000 questions to him by 1/6/2017, got paid $80 (UpWork takes 20% of the contract price) and got a stellar review from my first client!

How cool, right?!

Encouraged by my success with my first contract, I’ve submitted a few more proposals since and am pretty confident that I will secure at least 2 of the 5 contracts I bid on in the past three days.  (The first contract is a graphic design thing, producing quotation images, and the other contract is for an editor for an e-newsletter.  I have a “business call” about the editor contract on Monday at 1030.  I feel kind of…professional!)  So, with UpWork’s help, I’m an independent contractor!  My plan is to continue securing contracts and building my UpWork profile with positive employment history (and making some extra money) in preparation for my eventual departure from my current dictator job.  Being able to work from home, when I want, with no bullshit drama and miserable coworkers to deal with is pretty liberating.  I just hope that the ability to work for myself doesn’t amplify my disgust with my current employer too much over the next 4.8 years until I’m vested in my pension…

A related side note…my first client asked if I had a LinkedIn profile.  I didn’t respond because I didn’t know what the hell LinkedIn was.  I had to enlist Josh’s help to wrap my brain around what is, apparently, another social media platform.  (Are all of these connect-with-people sites really necessary?!)  It seems way less exhausting than Facebook and it seems like it might be professionally beneficial in my new and exciting adventure of independent contractor-ing.  So, now I have a LinkedIn.  And I have 12 friends.  Or links.  Or whatever the hell they’re called.  I know (and can tolerate) 12 people on LinkedIn!  Baby steps.

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