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FORWARD
The strategies I used to earn
$500,000 on Upwork
I've always been a freelancer, but I
never took my "side hustle" seriously
until I left my salaried job in the
corporate world behind in 2017.
It was shortly thereafter that my
brother-in-law (thankfully) suggested
I join a site called Upwork – the world's
largest freelance marketplace.
If you'd have told me back then that
just four years later I'd not only be
boasting about hitting the $500,000
mark on the platform but writing a
guide to help other freelancers do
the same, I would have thought you
were crazy!
But before I pass on the torch to a
new generation of Upworkers with
this Jumpstart Guide, I wanted to
offer a few programming notes:

1 These are the real strategies I used

The advice you will read on the pages that follow are strategies that I employed
when I was just starting out on Upwork, and some are strategies that I continue
to employ today to retain my 100% Job Success Score and my Expert Rated
badge.

However, it is important to note that, some things have changed since 2017
when I joined the platform. Select advice been adapted as needed.

This guide also assumes that you are already a trained intermediate to expert
professional with a service to offer. If you have no skills, I suggest that you
put this guide aside for now, and instead discover an in-demand niche and
focus on learning.

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2 This is the next best thing to one-on-one coaching

I realize that many cannot afford or are not interested in securing a private
business coach or a freelance coach. That is the reason I created this free
guide.

I am also a firm believer, as contradictory as this may sound, that no one

really needs a coach to be successful at freelance.

There are so many great freelancing blogs and vlogs and guides like this one
out there with loads of free information. I genuinely believe you have it within
you to do this on your own.

However, if you are interested in connecting with me one-on-one you can do

so on my newly launched Patreon channel where I also post screenshots
from my own Upwork profile, proposals and client communications.

It certainly never hurts to have someone you can call when you need a bit of
advice or a personalized critique.

3 I am not officially affiliated with Upwork Inc.

While I have a great relationship with the staff at Upwork, you should know
that this guide is not officially affiliated with Upwork Inc.

If you are interested in getting advice directly from the source, I encourage you
to check out their guides on getting started as a freelancer.

I cannot make any guarantee on individual results, but rest assured these
strategies have proven effective for both myself and many of those who I
coach one-on-one.

BONUS RESOURCES

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 BONUS
RESOURCES
Helpful tips and hot topics from
my most popular articles
Below you will find links to my most popular articles which cover a variety of
helpful topics.

• Upwork Readiness Test study guide and answers

• Upwork profile examples from 6-figure freelancers
• How to land your first job on Upwork (with proposal samples)
• Bad client red flags: 8 things to watch out for
• How to write an Upwork proposal (with sample)
• How to make good money on Upwork (10 tips)
• Mistakes you may be making on Upwork
• How to become Top Rated on Upwork
• How to ace an Upwork interview
• How to accept an interview or offer (with acceptance letter samples)
• How to get 5-star reviews on Upwork
• How to remove a bad review from your Upwork profile
• How to reduce Upwork fees
• What to do if your client asks for a lower rate
• How to ask your client for a higher rate (with sample)
• How to increase your rate on Upwork
• How do freelancers pay taxes? (and how to plan ahead)
• Best tools and software for freelancers (14 great resources)

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 WEEK 1
Polishing your profile, your
proposals and your pitch
Welcome to the exciting (and sometimes terrifying) world of Upwork. It’s a
platform that can feel quite intimidating for even the most experienced of
freelancers – but the payoff can be well worth your investment.

Week 1 is all about getting to know the platform and perfecting your pitch.
Don’t forget, this process is all about making constant tweaks to your strategy
until you find something that works.

If you have not yet created an Upwork account, please do so before

beginning this challenge. And feel free to work ahead if you so desire! Just
don’t burn through too many Upwork Connects during the first week.

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 DAY 1
1 DAY 2
2
Update your Upwork profile Take (and pass) the Upwork
using these tips. Readiness Test.

Create at least one of two You can use these test

proposal templates using answers as a study guide to
these tips. prepare.

DAY 3
3 DAY 4
4
Browse the Upwork Job Browse the Job Feed for a
Feed for jobs that suit your fresh batch of jobs, and send
skills. Use these tips for help at least 3 more proposals.
landing your first job. Send at If you need to purchase
least 3 proposals. additional Upwork Connects,
please do so now.

DAY 5
5 DAY 6
6
Browse the Job Feed for a Browse the Job Feed for a
fresh batch of jobs, and send fresh batch of jobs, and send
at least 3 more proposals. at least 3 more proposals.
Tweak your proposal slightly if Tweak your proposal slightly if
Day 4 produced no results. Day 5 produced no results.

DAY 7 & WEEKLY CHECK-IN

Day 7 is a mandatory rest day – your brain functions at its best after
7
you’ve had a break! If you need more than one rest day, listen to your
body. But don’t forget, there’s often less bidding competition on weekends
and holidays, which could give you a leg up on getting that first job.

If you didn’t get a nibble during your first week on those proposals, don’t
fret – it’s totally normal. It took me almost two weeks to get my first reply.
Just don’t burn through all your Upwork Connects too quickly.

If you’re already winning interviews – be sure to check out my tips for how
to nail an interview and how to secure a 5-star review.

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 WEEK 2
Your mission: Get that first
5-star review (or two!)
If you’ve made it to Week 2 – congrats. That’s a victory in itself!

It’s all too common for people to give up after an entire week of applying for
jobs if they aren’t getting a response or hearing back from clients, but that’s
par for the course on Upwork – even for the most seasoned freelancer!

If you’ve already landed a few interviews (or even won a few contracts) consider
yourself among the elite. Be sure to check out my tips for how to nail an
interview and my tips for how to get more 5-star reviews if you haven’t
already done so.

If not, don’t fret, this process takes time.

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 DAY 8
8 DAY 9
9
Reach out to a former client If you’ve run out of Upwork
and ask them to write a Connects, purchase a new
testimonial for your profile. pack or (preferred) upgrade to
a Freelancer Plus Account.
Apply for at least 3 new jobs
on the Upwork Job Feed. Apply for at least 3 new jobs.

DAY 10
10
Browse the Job Feed for a
fresh batch of jobs, and send
at least 3 new proposals.
Tweak your proposal slightly if
Days 3-9 produced no results.
DAY 11
11
Reach out to a second former
client and ask them to write a
testimonial for your profile.
Apply for at least 3 new jobs
on the Upwork Job Feed.

DAY 12
12 DAY 13
13
Add at least 2-3 items to your Browse the Job Feed for a
Upwork portfolio. fresh batch of jobs, and send
at least 2 new proposals.
Apply for at least 2 new jobs Tweak your proposal slightly
on the Upwork Job Feed. if Days 3-12 produced no
results.

DAY 14 & WEEKLY CHECK-IN

Day 14 is another mandatory rest day (assuming you don’t have any
14
deadlines due of course!)

Did you win your first interview this week? If so, congrats! It’s important to
remember as you go, even as you start to land jobs and win interviews, to
continue applying for new work (as much as you can handle).

DO NOT FORGET to ask for a 5-star review using these tips at the end of
each successful engagement. If you’ve asked and the client did not deliver
within a reasonable amount of time, politely ask again. Getting those first
couple of 5-star reviews on your profile are crucial to winning bigger and
better jobs.

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 WEEK 3
Stay focused, concentrate on
the long-term game
Welcome to Week 3!

If you’ve already landed a job or two, use this week to begin applying for
bigger and better jobs. If you already have a couple of 5-star reviews on your
profile, you may want to even take a moment to consider raising your hourly
rate! Use these tips if you need some guidance. Also, start to focus on more
“ongoing” or “long-term” contracts. Ongoing work means a lesser Upwork fee
and more income stability.

If you haven’t landed that first job yet, use this week to continue making small
tweaks to your proposal strategy, your Upwork portfolio (or a variety of case
studies if applicable), and really get into the head of your prospective client.
Ask yourself: “What would make ME reply to a proposal if I were the client?”

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 DAY 15
Already have steady work
15 DAY 16
Browse the Job Feed for a
16
coming in? Consider fresh batch of jobs, and send
bumping your hourly rate. at least 2 proposals. Tweak
your proposal slightly if Days
Either way, apply for at least 2 3-15 produced no results.
new jobs.

DAY 17
17
Browse the Job Feed for a
fresh batch of jobs, and send
at least 2 proposals. Tweak
your proposal slightly if Days
3-16 produced no results.
DAY 18
18
Reach out to another former
client and ask them to write a
testimonial for your profile.
Apply for at least 2 new jobs
on the Upwork Job Feed.

DAY 19
19 DAY 20
20
Add at least 2-3 items to your Browse the Job Feed for a
Upwork portfolio. fresh batch of jobs, and send
at least 2 new proposals.
Apply for at least 2 new jobs Tweak your proposal slightly
on the Upwork Job Feed. if Days 3-19 produced no
results.

DAY 21 & WEEKLY CHECK-IN

Today is another mandatory rest day.
21
By now, you are surely noticing a theme starting to develop. As I mentioned
earlier, your first few weeks on Upwork are all about constant iteration and
constant tweaking.

If you are at the point where you feel like you have a decent workload going,
proceed to Week 4.

If not, repeat Week 3 until you’re receiving a steady stream of interviews

and income. Consider asking a friend or colleague to review your profile,
portfolio and proposals. I also offer these services on Patreon.

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 WEEK 4
The journey to Top Rated
status begins here
Welcome to Week 4! You’ll be relieved to hear that the hardest part is over.

If you continue to turn in stellar work for your clients, you will be well on
your way to receiving the Rising Talent Upwork Badge (in as little as 30 days),
followed by the Top Rated Plus Badge (in as little as 16 weeks), and then finally
Top Rated Plus (after 12 months if over $20,000 has been earned). Learn how
to obtain these badges here.

Each badge comes with its own perks like reduced fees on Featured Jobs,
faster payments and access to Upwork Talent Specialists. You will also start
to receive more Job Invites as time goes on, which means no Upwork Connects
are required to reply. Upwork Invites are the real secret to Upwork Success
(more on that later).

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 DAY 22
Bump your hourly profile
22
rate now. If you’ve already
bumped your rate once in the
last 22 days and continued to
receive new work, consider
doing so again.
DAY 23
If you have the capacity to
23
take on additional work, test
out that new higher hourly
rate by applying for a 2 new
jobs.

DAY 24
24 DAY 25
25
Update your availability Add your completed
as you start to take on new Upwork jobs to your Upwork
work. Keeping this updated is portfolio. Make sure to
crucial to obtaining the Rising include relevant keywords to
Talent badge. improve the Upwork search
algorithm.

DAY 26
26
If you have the capacity to
take on additional work, test
out that new higher hourly
rate by applying for a couple
of jobs.
DAY 27
27
Consider downgrading your
Freelancer Plus membership
if you feel you no longer need
the extra Upwork Connects.

DAY 28 & NEXT STEPS

Today is a mandatory celebration day. You’ve officially reached the end of
28
your 28-Day Upwork Challenge. Congratulations!

It’s now time to look to the future. To achieve long-term success on the
Upwork platform, it is important to focus on obtaining and retaining those
Upwork Badges we mentioned earlier (details here).

After you achieve those badges, you’ll notice that it gets easier with each
passing day to find quality clients and land jobs. You’ll even decrease your
dependency on Upwork Connects (all of my jobs come through invites now),
and steadily decrease your Upwork fees by continuing to focus on ongoing
contracts and long-term projects.

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 ABOUT ME
Meet Morgan Overholt
I have nearly 20 years of professional experience in graphic design and sales. I am a
self-described small business evangelist.

After spending the first 15 years of my career in mostly corporate settings, in 2017,
I decided to take the leap and turn my then part-time freelance side hustle into a
full-time business. In the years that followed, my solo-freelance act blossomed into a
small design agency, Morgan Media LLC.

Today, Morgan Media LLC continues to serve our graphic design clients with a
concierge level service. In addition to being actively involved with our agency, I also
freelance on Upwork, am a regular contributor for Business Insider and Collective,
run a small shared office space in Miami, coach other freelancers on how to follow in
my footsteps and own and operate two blogs: TheSmokies.com and MorganOverholt.
com.

I want to hear from you

Did you find this guide helpful? Did I leave anything out? Do I need to add more detail
on a specific topic?

I would love to hear from you so that I continue to tweak this guide and help future
freelancers.

Constructive and kind criticism only please. I created this free guide on my own free
time as a public service to help others.

If you loved it, I’d appreciate it if you connected with me on Patreon, Twitter, Facebook
and Instagram using the links below.

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