As we transition out of the summer and into the fall, I think now is the perfect time to talk about the importance of planning for the feast or famine cycle freelancers typically experience at different points in the year and which marketing strategies are still the most effective for those in the industry. One of those is Upwork. In this episode, I discuss five reasons why I believe the online job site is still well worth it going into 2018. 

Full Transcript:

Hey there! Welcome back to the Better Biz Academy podcast. As we move out of the summer and into the fall, I think it’s really important to talk about which marketing methods are still really valuable for freelancers. Now if your business is like mine, things always pick up in the fall.

However, in the last couple of months, my freelance business has actually doubled and I have been completely booked over the summer, which is a relatively new experience for me because I usually go on vacation for two or three weeks, I take advantage of the downtime and the fact that not a lot of people are in their offices, etc. over the summer, but I picked up a number of huge contracts in May and June that have kept me fully booked.

Even knowing this, I still think it’s valuable to think ahead about the fall because even when you have a fully booked roster, certain projects will come to a close, certain clients may no longer fit your needs or the direction that you are taking your business and it may be time to end those contracts and look to bigger and better things in the fall.

And usually every year, September through November are some of my biggest months and then we will go through a slow season again. Around December and January, a lot of people are out for the holidays or working reduced hours and then after that, return-to-work January rush, everybody’s New Year’s resolutions also affect their business. So, they are thinking about content marketing, they’ll be considering how to go forward with content marketing in 2018 or whatever year it might be and they’ll be open to having those conversations again.

The slow season is the perfect opportunity to re-evaluate your business & marketing efforts

As a freelancer, I really recommend you to take advantage of these busy and slow seasons. A lot of times people will say, I am pitching all summer and not getting any response. This is a great time to re-evaluate your rates, take a look at your writing samples and make sure that they are top notch again and to develop a marketing plan for the busy months that will follow. That way you can fit in some vacation as well. I try to time my vacations and time-off to coincide with when my clients are not in the office or when people are generally not thinking about content marketing because it makes it easier for me to step away. So, I would never really schedule a vacation in the middle of September because I know that I’ll be working a lot during September. So, I will usually try to have my vacations coincide; last year I went on vacation for three weeks for the last week of July forward and that really worked well because a lot of people weren’t even in the office. It really didn’t affect any of my clients who are on retainers or ordering a particular number of blog posts every single month.

So, now that I have addressed that, we are going to talk in a future episode about how to get ready for freelance busy season and the steps that you need to take in order to be prepared to do that and to make the most out of it because you can really garner a lot of business, and not just one of projects, but really long-term opportunities during these freelance busy seasons.

And I find that allowing your business to ebb and flow with the natural cues of the market can be really, really valuable and I recommend you consider it. So, the question I want to consider today has always been something that is part of my marketing plan, regardless of the season, but it’s so controversial in the freelance world. In fact, a lot of people who are freelancing gurus or they have their own courses about freelancing and blogs about it will say to never ever use Upwork. And in fact, I heard a podcast several months ago with that exact title-Why you should never ever use Upwork.

So I contacted Bryce, the manager of the Clients from Hell podcast, the guy who runs it because it was really about one particular person’s story and how horrible it was with this client that they had from Upwork and ultimately the end of the story was that the client was terrible, but Upwork management was pretty good at trying to help this freelancer get through this difficult situation.

However, I find this idea of never using Upwork comes up a lot. In fact, if you have done any research at all about other people in the space of freelance marketing tips and things like that, they will tell you to never use Upwork and frankly, I am okay with that advice because it keeps my competition down. Like it sounds crazy, even though I have a course on how to make a killing on Upwork, I am happy to teach people how to do it, but the fact that so many people are saying, “You should never use it”, “It’s all low-end gigs”, “It’s a total waste of time” – that’s fine with me because they are practicing what they preach with another email marketing method or another way of reaching out to people like in-person networking etc. So, that’s fine. My bottom line for any freelancer is always this: find a method that works for you.

Upwork’s effectiveness as a marketing strategy depends on consistent effort

One mistake that people make is they try a new marketing method and then they don’t allow it to stick. So, if you are going to try Upwork for two weeks and see if it turns into any leads and then you get frustrated when it doesn’t-I wouldn’t be surprised because you didn’t put in any consistency there and that’s true whether you are doing cold calls, email marketing, pitching on other job boards, in-person networking, direct mail campaigns. You have to be consistent in order to see a difference with those opportunities. So, I encourage you that regardless of what you pick, find something that works for you, but give it a chance. Give it a month or two months of you consistently working that method to see if you are getting any traction because it can take a while.

I am currently in a mastermind with a group of people who are doing a lot of cold email pitches and some of them are sending out 50 to 100 pitches per week. Not all of those are landing. They may only be getting a couple of phone calls from that and these are high level freelancers. So, never take it as a negative sign unless you have been pitching or using Upwork for six months or a year and you have literally had zero jobs and zero opportunity to prove yourself. Then there is something going wrong. That method isn’t working for you or your samples aren’t speaking to the client or your pitch is off. And again, a future upcoming episode will focus a little bit more on things that people do wrong at the beginning of those relationships that are costing them clients. I recently had the opportunity to evaluate more than 200 writers for a client of mine and it was alarming. The type of mistakes that were made, not just with the pitching process, but in handling the relationship professionally. So, that will be the topic of a future episode. But for today, I want to dig a little more into this idea of Upwork because a lot of people just think, “Oh well, this isn’t going to work for me. It’s not worth my time and everybody is saying not to do it.” But there are five reasons that I think Upwork is still worth it in 2017 and 2018.


5 Reasons Why Upwork is definitely Worth it 

1. Upwork is still the biggest job marketplace in the world

Now I have shared many times and I’ll share it again. At the time of this recording, Upwork has contributed more than $300,000 in leads to my freelance business over the last couple of years. It’s not the bulk of my income, however, it has been an excellent lead generation tool for two reasons.

First of all, my Upwork profile shows excellent feedback, so even if I met someone through cold email pitching and they Google me and they see my Upwork profile, but aren’t hiring me through Upwork because we met another way, that still benefits my business because it’s a great way to show my track record.

Furthermore, Upwork is still the biggest job marketplace in the world and that’s actually reason number one why you should still consider it. Yes, there are plenty of low paying jobs on Upwork. You have to be willing to sort through those to find the gem job opportunities. I found $25,000, $30,000 and $50,000 contracts on Upwork and landed the client within two hours, simply using the same strategies that I developed years ago for landing business on Upwork. So, that’s reason number one: it’s still the most popular job board site, it’s still the first place that many people go to find leads and you can find some amazing opportunities on there with great companies. I had an opportunity last year to work as a project manager for a company that was handling a very huge portion of Disney’s operations and I never would have had a chance to get my foot in the door with somebody working with Disney or any other high level company, had it not been for Upwork providing that opportunity for me to meet the client. So, it’s still worth considering in 2017 and 2018 because so many people are still using it.

2. Your online portfolio on Upwork acts as social proof for potential clients

The second reason that I think Upwork is still valuable as a marketing tool is this idea that it provides you an additional online portfolio. Hiring a stranger online, while it’s getting more common, is still really scary for a client. Having a portfolio where people have left you direct feedback, whether its LinkedIn and your clients are leaving endorsements and recommendations on there or Upwork, is really valuable because think about the social proof that you look into before you purchase a service or product. You look at the reviews on Yelp! or on Google or on Facebook or on Amazon and you read what other people have to say. Likewise, the feedback system on Upwork allows your clients to see kind of that you have been pre-vetted. Someone else has already hired you and been happy with the work. Now this is a double-edged sword because if you don’t deliver a great experience for your Upwork clients, they are going to leave you poor feedback and it’s very difficult to recover from poor feedback. So, when you do land a job on Upwork, you need to go above and beyond by delivering an outstanding and easy experience for your client.


3. Upwork leads are pre-qualified. They are ready to hire!

The third reason that I love Upwork and I think it’s still valuable as a marketing technique; this is probably the biggest one for me. The leads are pre-qualified. So, if I go out and cold pitch people, many times that includes an educational piece. If I go out and pitch somebody and say, I’d like to write SEO blogs for you, half the people, at least, will write back and say what are blogs and what is SEO. That means hours of my time having to convince this person that this service is valuable and they need it, to begin with. Whereas, someone who is posting a job on Upwork already knows they need the help. I don’t have to convince them about the importance of SEO or blogging on a regular basis. They already know, they have already come to terms with that and are looking to hire someone to help them with it. So, much less work on the freelancer’s end because the client is pre-sold. The client is also ready to buy now. They would not post a job on Upwork, if they weren’t interested in hiring someone immediately and being able to turn to a freelancer for this work right away.

If you are cultivating leads another way, the process of converting someone can take forever. I know many freelancers who have to cultivate these leads for months and months and for one of my non-Upwork clients, we were in conversations for over a year before they finally signed. Now that was a very big project, so it took a while for the client to get organized but it took over a year. So sometimes that’s really not beneficial for the freelancer if you don’t have other leads in the pipeline. The fact that your leads are prequalified on Upwork makes your job easier because you are only convincing them to hire you, not about the value of the project overall.


4. It can be a great way to land business quickly

And this sort of ties into the fourth reason that I think Upwork is still worth it and that’s quick work. Whenever your business is slow or whenever you need to ramp things up pretty quickly, Upwork can be a great way to land business right away. Because, like I said, those clients are already prepared to hire somebody. They are at the point of closing out this decision loop and being done. So, I approach things the same way in my business when I am ready to hire someone, pay for a service, do something. I take action immediately. I don’t want to post a job and then wait six months and try to figure it out and see if that person is still available and if their prices have changed. When I post a job, I am ready to hire now. So, that means quick potential work for the freelancer.

Now it does take some time to get paid through the Upwork process. It can take 7 to 10 days, depending on the type of job. It could even take longer, if say you are on an hourly contract, you do the work on a Monday, then you are waiting a full week beyond that for your timesheet to even be submitted then it’s going to be a week beyond that for you to get paid that following Wednesday. So, it can take up to 2.5 weeks, if you are an hourly contract. This timeline is shorter, if you are doing fixed price Escrow jobs. But I love the fact that it’s quick work. It’s a great way to find leads immediately. These people are ready to buy and hire and you are simply giving them the opportunity to do that. And so, I think it’s very hard to find another place where you could close business that quickly.

Upwork is, in my opinion, the number one way to do it and I have done it time and time again. I have challenged myself with my own Upwork marketing methods. At the start of 2017 when I fired a client who was making up about $2800 to $3500 worth of work every single month, I made it a challenge to replace that particular piece of income, and I worked really hard just biding on Upwork. I did not tap into any of my other resources like recurring or current clients and asking for testimonials or referrals and all that. I chose to focus on Upwork completely because the marketplace is such that other freelance advice givers are always saying, oh it’s a total waste of your time, don’t ever go on Upwork, it’s the worst website in the world. So, I am like “Okay, I have to challenge myself. I have to prove that this still works.” I replaced all of that lost income and more using Upwork. And I have done that at least four or five times, when a contract has ended or it’s time to move on to something new.

So, I still check Upwork on a regular basis, but because I am fully booked, I only bid on jobs that would be a perfect fit for me, where I could potentially fit it in, in the future. So, even when you are busy, Upwork is a great source of leads because there may be someone who needs to take some time to hire you. There are some jobs where you’ll submit a proposal and the person will want to schedule a phone call with you immediately and you will go into the process of completing the job right away. Other clients, however, could take two weeks. This is particularly true with agencies or anyone who has to get approval from a higher up, they are probably going to run all the potential candidates by that manager, supervisor, then make a decision to hire you, then there is on boarding. However, I find that the timeline is often compressed, when you are using Upwork as opposed to some other way of generating leads.

So, in 2017 and in 2018, a freelancer has many different marketing opportunities. You have got to find something that works for you and you have to make the commitment to be consistent with it because if you are dropping in here and there, submitting two or three jobs proposals per week on Upwork, you are unlikely to see a return on your investment because you are just not putting in the time and the consistency, and that’s true with any marketing technique. If I send out one cold email pitch every week, there is not much of a chance of hearing back from that because I am just not giving a wide enough net to capture my leads. So, because Upwork allows you to get this quick work and because the people are pre-sold, it’s so much easier to drum up that business and use this site as additional online portfolio.

You have got to make the decision that’s right for you. For some people, Upwork may not be the right fit. If you are highly niched and you write about one specific thing, for example, I knew a writer who focused only on maritime injuries and he wanted contracts just for that. Upwork’s not going to be the best fit for you. You’re going to find more general jobs, you are going to find lots of medical postings where you can write blogs in the medical industry or you could find legal postings for blogs and webpages in that industry, but they are going to specifically be maritime. So, that’s really not the best marketing approach for that candidate because he or she would need to go another route of identifying the top clients in that particular industry and pitching them directly. That’s going to be much more effective.

However, for someone who has niched down a little bit or someone who is the generalist, Upwork can be a great source of leads. People still use it all the time and I know many people who have landed high dollar, valuable, ongoing contracts using Upwork. Now this is true no matter what type freelancer you are. It can be more competitive in some of the fields like graphic design and web design, but there is still an opportunity to get your foot in the door to developed this portfolio, to get some work experience, delivering things for clients, understanding your deadlines and timelines better and then ultimately you can decide to leave Upwork if you wanted. If you want to focus your marketing efforts on something else and this hasn’t really gotten the traction you want or you think it would be easier or faster for you to do something else, be open to that change. But don’t commit to any marketing method unless you are ready to be consistent because I guarantee it will not generate the ROI that you are looking for if it’s just sort of here and there; you are not going to see results.

Please stop expecting that you can bid on ten jobs on Upwork and that you are going to land eight of them. You may not even hear back from any of those clients. You have to be consistent. And you also need to be reflective about what you are submitting to clients, and I’ll cover this in much more detail in an upcoming episode, but you need to be submitting materials that are your best work. That means your best pitch, your best work samples.


5. Upwork takes away the hassle of payment processing

Upwork, in my opinion, is still worth it in 2107 and 2018 because it is a very valuable way to connect with your ideal clients and generate business quickly. The fact that Upwork manages the payment is just one more bonus for you. This is particularly valuable for new freelancers, who may be concerned about setting up an invoicing system. They may be worried about not getting paid by their clients etc. Having Upwork manage the escrow or the hourly payments gives you some sense of confidence that you are actually going to get paid. There are lots of horror stories out there about Upwork. In fact, I have had probably two or three clients over the course of my Upwork/Elance career that have been horrible or that I have had to refund, but that’s out of hundreds. So, keep that in perspective.

If you had a hundred different bosses, you probably wouldn’t like several of them, right. If you have had a hundred different customers in a traditional brick and mortar business, not all of them would be stellar either. So, I encourage you to keep that in mind as you figure out whether Upwork is right for you.

If you are listening to this podcast when it first airs, then I strongly recommend that you re-evaluate your materials carefully. I bundle together one of my award-winning courses; “The Guide to Killing it on Upwork” with my original SEO writing mentor, Yuwanda Black of Inkwell Editorial.

Together our jumpstart package allows you to learn everything you need to know about writing SEO blogs and how to land business on Upwork. We have put this together for you based on more than 25 years of combined experience in the field and I am very serious about helping you land business because I care about bringing freelancing into the mainstream and making it accessible to more people who want that freedom and flexibility.

Learn more about our freelance jumpstart pack below by taking a look at the show notes and there is the link to the course there. There is a lot of amazing material in there. Everything I know about SEO writing, I learned from Yuwanda Black, she is fabulous, her materials are in-depth and it is the easiest way to break into the freelancing world and quite easy on Upwork because there are so many SEO blog writing jobs. So, I encourage you to take a look at how my strategies with Upwork in that course and how Yuwanda’s strategies about becoming a great SEO blog writer, including how to make writing samples, can help you get to the next level in your freelance business.

Thanks again for tuning in. I look forward to speaking with you next time. If you have any ideas for a future episode or there has been a burning question about freelancing you’d like to see answered, drop a line to

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