Step 4: How to find work experience that gets you hired

This is step 4 of the road map to get your first (or next) job. This is part of how you break out of the unemployment cycle: by finding real work experience as a recent graduate.

After making a resume and an online presence for yourself, you might still be left without the kind of experience you need to get the job you want.

That’s exactly what we’re going to solve here.

It’s tough to make it out there. Plenty of companies look for any excuse to find cheaper labour, and this leaves you with a catch-22: you don’t have the experience to get a solid job, but you can’t develop the experience because you don’t have a job. This is a part of what makes entry-level job searching so soul-sucking.

This step in the road map will show you how to break out of that catch-22, giving you the work experience you need to build a proper portfolio and rock interviews.

Table of Contents

Identify the skills you need to develop

Create a list of prospects with business pains

Approach your prospects like a professional salesperson

Set the scope for each work experience project

Analyze your success and measure the results

Identify the skills and work experience you need to develop

There’s no getting around a lack of work experience in the long run, and you’ll do yourself no favors by faking it in the interview. Robert Half reports that 42% of applicants aren’t qualified, while Workopolis reports that up to 75% aren’t qualified.

This step in the road map teaches you to make yourself qualified, putting you squarely above 42%-75% of the rest of the job applicants out there.


Up to 75% of job applicants aren't qualified for the jobs they pursue.

You don’t want to get bogged down in make-work projects, or to become the victim of never-ending requests from the prospects you’re about to research.

That’s why it pays to be strategic. Figure out what kind of experience you’re missing so that you can start thinking about the projects you want to take on to build them. There are a few ways to do that, depending on where you are in your job search.

Study job postings from Indeed and LinkedIn

This is the fastest and easiest way to find the skills you need. Scan a few job postings for keywords, skills, industry tools, and common phrases. From there, compile a list of the most common and important ones that you find. You’ll connect them to projects that you can finish.


Signup for career advice on LinkedIn

Check out LinkedIn’s recently added Career Advice feature. It pairs you up with more experienced people in your industry, letting you ask questions of people who have anywhere from 4-40 years of experience on you. You might even find some long-term mentors here, which is a huge win.

Ask for interview feedback if you get a pass

This one is the hardest to do, but it can also become the most valuable way of learning which skills you need to acquire before that employer (or another one like it) will hire you. Not all interviewers are willing to share, and some just don’t respond in general, but it’s always worth your time to find out.

Let’s look at this sample job ad. We tell immediately that these things are essential:

  • Social media proficiency
  • Editorial skills and mindset
  • Experience scheduling calendars
  • Good interpersonal skills
  • Engaging at live events
  • Practiced in reputation management
  • Comfortable with social analytics

Some of the skills in this sample job ad are “soft,” but many of them fall under the “hard skills and technology proficiency” category.

If this is the kind of position you want, then it’s clear that you’ll need to start managing some social media profiles—but instead of just posting some generic stuff on an existing Facebook account, you could start a YouTube channel for someone.

That’s the kind of project that would check multiple boxes at once, including:

Experience with YouTube, which is difficult to master

Experience creating video content (also difficult)

Experience leading a team (and non-marketers) on social platforms

Experience building a community for a brand-new social channel

Measuring success for every video you upload and share

Taking on a project like that would put you in good standing. Taking on three (with measurable results and lessons learned) would make you front-runner. Most of the people competing for these jobs with you don’t have much or any real-world experience of their own—and that’s why building experience for yourself will put you ahead of at least 80% of the other applicants.

A word to the wise: You should not weigh yourself down with unrealistic expectations to develop all of these skills in a week, or even a month. Give yourself realistic deadlines to find prospects, agree on project paramters, and especially to learn the ropes. Focus on a handful of skills that will give you a competitive edge to get yourself a job sooner than later, but do it with the understanding that nothing happens overnight.

When I was unemployed, I focused on making myself a more employable content writer for marketing agencies by focusing on:

  • Building up a ghost writing content portfolio
  • Getting experience managing social media accounts
  • Developing my interpersonal skills for account management

You’ll notice that writing and interpersonal skills aren’t even hard skills. Learning the hard skills was definitely a trial by fire when I got the job, but it could all be learned with dedication and a few late nights. Having a website helped, too.

Then things started to get easier. I got to take on more projects, manage more people, and start getting in on strategy development.

Use all of these tactics to create a list of 10-15 skills you should develop for the job(s) you want. Focus on hard skills or technological proficiency, but don’t ignore important soft skills. If you have some of these skills already but you suspect interviewers don’t believe you (it’s happened to me more than once), then keep that in mind for the next few steps and choose a project that lets you demonstrate those skills with measurable results.

Create a list of prospects with business pains

Now that you have an idea of the skills you want to learn and the kinds of projects you’re able to take on to do so, it’s time to look at prospects. Think of it like volunteer or pro bono work.

This is where you want to start looking for work experience to take on:

Friends starting out

People start freelance businesses and other kinds of side hustles all the time. Some just work solo with corporate support structures, like financial advisors.


Agencies are always strapped for time and cash—especially the small, local ones that are trying to make a name for themselves. Agency juniors are basically you.


Tread carefully here. Startups are notorious for having an elitist culture, zero time or project management skills, and being cheap. But you can still take advantage.

Your own side project

Sometimes all you need is a passion project to demonstrate your skills to the world while doing something you love. Case in point: this could be one of my portfolio project.


Normally I wouldn’t condone doing free work, especially as a freelancer—but that’s usually because the people seeking the free work to be done for them usually lack a moral compass. The difference here is that you’re setting a defined scope for a limited amount of projects to build your resume and portfolio, in turn making you a much more viable candidate to do it for money as an employee.

There’s a lot of opportunity to get your foot in the door if you’re willing to do a limited amount of projects for the competitive price of free. Some of the people out there looking for that free work can be pretty foul, but you’ll also be able to find people and projects out there that you really believe in. I did, and I’m glad I worked with most of them.

Squarespace project

I helped a brand-new real estate agent build her website on Squarespace, including the content. I met her at a new year’s party.

Email campaign

I created digital content and an email marketing strategy for a local non-profit in the heritage sector at a family friend’s request.

Executive ghost writing

I approached an old acquaintance about ghost writing for her. Several of those articles live on now.

Agency freelance

I approached a local agency about freelance content writing. It went so well that it led to an interview.

Business development

I turned the business development aspect of my freelance business into a portfolio item, demonstrating my soft skills and personal drive.

My own website

Creating a website in Squarespace was its own project full of skill development. Agencies even complimented me on it. It stood out.

Academic journal

I took an extracurricular activity and turned it into a case study: recruiting academics and editing their work for publication.

Club experience

I turned experience in co-managing a university club into miniature case studies to add problem-solving examples to my resume.

In my case, it was a combination of writing projects, my portfolio website, and teaching experience that got me noticed (the freelance experience helped, too). The only thing I didn’t pursue as a portfolio project while job searching was the teaching-related experience, but even that isn’t outside of your reach. You can always volunteer at a college writing center or tutor students in some other discipline to gain experience. Track the students’ grades on assignments or over the course of a semester to measure your results!

Pro tip: Limit this to 3 portfolio projects for now. You don’t want to get lost in doing free work for people; you want to take on a limited amount of work to develop specific skills and to measure the results in a timely manner so that you can beef up your resume and talk about overcoming challenges in cover letters and interviews. The work experience you gain here is the means, not the end goal.

Eventually you’ll build your portfolio naturally through your job. What we’re doing here is breaking the mold by setting you up with three projects to put you on interview short lists.

Think: who do you know that’s just starting out, strapped for cash, or just way out of their depth? Who in your network just needs someone in their corner to get past some hurdles?

What organization could use volunteer help with the skills and knowledge your program taught you?

  • Does a friend or acquaintance need a marketing plan?
  • Does a non-profit organization need communication material written?
  • Does a local coach need a basic website made?
  • Could a local restaurant use some social media management?
  • Does a nearby school need someone to do the quarterly newsletter?
  • Perhaps a business improvement organization could use communications help?
  • Have you always wanted to take on a side project close to your heart?

Create a list of these people you know—even just tenuously—and figure out what kind of work you could do for them. Don’t discount anyone or anything just yet, because that list will get shorter once you start prospecting. Some people just don’t always need work done, but someone always does.

Word to the wise: Not everyone will want help from someone just starting out. Retail chains, high-end restaurants, and established mid-sized companies may think twice about inviting an “intern” (of sorts) into their ranks. The more established the organization, the more resources it’ll have to solve business pains on its own.

That’s why it’s usually worthwhile to pursue entrepreneurs, small businesses, and non-profits that have more acute business pains yet too few resources to handle hem all. Shoot for the low-hanging fruit, for now.

Approach your prospects like a professional salesperson

It’s easy enough to reach out to your friends and classmates, since you know them already.

Reaching out to people you’ve never met before requires a bit more finesse, but it’s totally doable. Some people make entire careers out of it. We’ll start you off with some process, though.

Here’s how to find the right people for the organizations you want to work with:

  • Website “about” or “contact” pages
  • Social media profiles
  • LinkedIn prospecting
  • Email prospecting

The first two methods are straightforward; you know how to navigate a website and how to lurk people’s social profiles. The other two take a bit more know-how, so we’ll focus on those in the next section.

The LinkedIn prospecting process to find work experience

This method is generally straightforward, but I’ll outline the process in case you’ve never used LinkedIn like a salesperson before.

First, find the company’s page on LinkedIn. You’ll notice that each page has a small link mentioning how many people work at that company. Click on it.

That brings you to a list of people who work at the company. Search for the most relevant person to you; it’ll probably be a mid-level or upper-middle employee who manages something, but not quite at the “Director” level.

Continuing with the example of trying to become an agency content writer, this is the person on the employee list that I would want to pursue: the “Content Specialist and Editorial Manager.”

I can infer that this person oversees most or all content writing operations, making her the ideal person with whom to build a professional relationship.

Click on the profile and scan it to make sure the person still seems relevant after you’ve taken in a bit more detail. If not, go back to the list and find the runner-up.

Once it seems like a good fit, follow the person. That will let you keep an eye on the point of contact in your news feed so that you can engage with them and stay in that person’s orbit, even if they don’t have the bandwidth to work with you right now.

Then connect with the person—but read this first: you need to personalize your connection request with a sincere message. We’ll get to that further down in this section.

Pro tip: LinkedIn’s mobile app is awesome, but it has the unfortunate flaw of sending generic connection requests as soon as you hit the “connect” button. This leaves you looking like a desperate college graduate instead of a well-put-together professional on the rise.

I’d recommend doing this part on a desktop device to minimize the chance of accidentally firing off generic connection requests, which would sour prospects’ first impressions of you.

The email prospecting process

You can’t find everyone over LinkedIn, and some people just don’t log in all that often. That’s why our next step will involve finding email addresses for those prospects. There are a few competing software platforms out there for sourcing business emails. Not all of them are great, but there’s one that has impressed me since 2017:

And it comes with a free plan.

There are two ways to use it:

  • Copy and paste the company website’s URL into the search bar on, or;
  • Install the Chrome extension and just click on it when you’re visiting the company’s website.

Just be aware that Hunter limits you to 50 searches per month on the free plan. If you already have your list of 20 prospects, then it’ll be more than enough for your purposes.

What to say when you reach out to prospects

I’d recommend creating a personal message that introduces yourself and makes it clear that you want to find work experience. Honesty goes a long way, and you’d be surprised at how many people are eager to connect with an ambitious up-and-comer—people like that can be recruited, and they tend to become valuable connections in the future. Be that person.

Just give yourself time to read it again before hitting the send button the first few times.

Don’t fret if people don’t respond—that’s why we’re following them on LinkedIn, too. This will make their activities pop up in your newsfeed so that you can work your way into their orbit by engaging with them, becoming a more familiar entity to them.

It’s also just part of how sales work (and this is exactly what salespeople do). For context: salespeople who close 10% of their leads are considered good at what they do, so if you only end up working on 2 projects on that list of 20 prospects, then you’re doing a great job.

Respecting people’s time, appearing confident, and conveying humble gratitude is the best barometer to use for email outreach. Remember that in your follow-up conversations, too!

Pro tip: People will respect you more if you respect yourself. Don’t talk about doing free work in your outreach email, or else the recipients might assume your work isn’t up to a professional quality.

Just talk about working on projects together. Some might even assume you’re a freelancer and ask about your rates.

Set the scope for each work experience project

Setting the scope of your project with each client doesn’t have to be set in stone—growing with them to take on new responsibilities is a good thing—but you want to make sure that you’re not doing too little or doing too much.

The difference between growing with the client and doing too much can be subtle, but it’s an important distinction. Your first clue will be if a prospect wants you to take care of mundane tasks instead of the problem-solving project you’re proposing. Be wary of these ones; you might still be able to get what you need out of the project, but keep an eye on how much “busy work” gets thrown your way. If you end up becoming a button-pushing intern instead of building up your work experience with the interesting stuff, then it’s time to renegotiate the responsibilities or to say goodbye.

Growing with the client

This is where you’ve proven yourself by delivering good work and meeting your deadlines. The client likes working with you, communication is generally clear, and the vibes are positive. This happens after the initial probationary period that mark the beginning of most business relationships (especially with freelancers and new employees).

Being taken advantage of

Marketing agencies have to deal with this on a daily basis. They call it “scope creep.” It’s when the client asks more and more from you for no additional reward, and it adds up to so much that you end up spending your time on inane tasks instead of focusing on doing what’s actually valuable. Do not become a button-pushing monkey for clients.

Ideally, you’ll also want to get a written recommendation and some skill endorsements on LinkedIn. That makes it fairly important to maintain a good relationship with your prospects (soon to be clients) throughout the course of your project for them.

Word to the wise: Not every portfolio project needs a testimonial to be worthwhile, but it definitely helps to have one. These come in the form of written recommendations for your LinkedIn profile, testimonial snippets for portfolio websites, and—if you’re starting a consulting business of some kind—even Google reviews.

Some of my portfolio projects worked without testimonials, but they would have been significantly more effective if they came with positive feedback for the rest of the world to see. Out of the three work experience projects you’re pursuing, get LinkedIn recommendations for at least two of them.

With that distinction in mind, focus on finding the pain points for your prospect’s organization. You should absolutely research the organization ahead of time to get a sense of what it might need and what it doesn’t; why would anyone let you perform a work experience project for them if you hadn’t even put in the effort to learn about them beforehand?

Check out these sources to learn about prospects around the web:

  • The website (obviously) to see how it runs, what it does, and how it communicates.
  • Company reviews on Glassdoor and LinkedIn to see some more internal business pains.
  • Check out the executives and/or relevant contacts on LinkedIn to see what they’ve been working on (I told you this would come in handy!).
  • Social media profiles to see its recent events and customer service mentality.

You may notice some things that make you cringe, or you might even just think “that could have been done just a little bit better.” Those are the moments you’re looking for! Write down what you find when you have those reactions prospects, and figure out how you might be able to improve on that process or production.

If you’re not sure what to look for, then use this list of examples to get started. Some will be apparent from the outside, but some of them might only be apparent after speaking with a contact from the organization.

Can’t fill a position

Poor communication

Needs proposals written

Needs a website

Misses deadlines

Needs market research

No social media presence

No documented processes

Those are all problems worth solving. Some of them apply to individuals and some of them apply to teams. Every “client” of yours will have a different mixture of business pains, so think about what you could solve or improve for every prospect on your list.

What you’re ultimately looking for in these projects is a a way to create a positive and measurable result, or some kind of creation that speaks for itself.

For example, it’s hard to measure the success of creating a website other than “look, I made this.” But that’s okay because it speaks for itself; someone else can follow a link, see it, read it, and interact with it. There’s a certain skill set involved with its creation that touches on design, writing, website management, and technical integrations.

That’s a tall order for a recent graduate though—I certainly didn’t have the skills to attempt that for a few years after graduating. Instead, look for ways to add value in the form of:

  • creating a publicly visible piece of work
  • conserving resources (including time)
  • saving money
  • measuring something simple (e.g. event attendees)

Ask about these kinds of business pains when you’re speaking to contacts. Just remember to introduce yourself, explain what you’re working to achieve, and learn about both the organization and the point of contact who has graciously put aside time to speak with you before diving into the brass tacks of business pains. It’s just good table manners.

Pro tip: Don’t try to seal the deal during your first face-to-face meeting unless it seems like the other person is definitely on board. You’re establishing a relationship with this person and the larger organization behind that person. While you may have had your eye on them both for a week or more, they’ve just met you. Give them some time to mull it over, look you up online, sleep on it, get approval from their boss, and so on.

Pushing too hard for a work experience project right off the bat is going to backfire. Be patient and attentive, but not aggressive.

Even matches made in heaven might take a week or two to come together after you have a dedicated meeting. Be patient and work on setting up other leads in the downtime (or get a head start on the next step in the road map: making a portfolio website).

Over the course of a few interactions you’ll come to an greed-upon project. Don’t stray too far outside of the scope, either. If you’re writing a blog or two for the organization, don’t get sucked into writing 5 for nothing in return with the promise of an eventual recommendation dangling over your head.

Once you have a project set out (even just a few trials or mini-projects), then you’re well on your way! Next we’ll look at how to measure success for these projects so that you can build up a resume that clearly communicates how you solve problems and add value.

Measure your work experience project results

At the end of every project you’re going to analyze how it performed and how you grew. Then you’re going to fit it into the PAR format that we used in Step 1: Building your resume.

The PAR format follows three basic steps of a narrative arc’s beginning-middle-end format—just adapted for the world of business.




This turns you into the magic that separates a business’ proverbial “before” and “after” photos, all wrapped up in brief case study.

That’s it. It’s not about how many sentences you use—it’s about communicating the business problem, what you did (and how you did it), and then the result. It could be 2 sentences, 2 paragraphs, or two pages.

If you’re tackling smaller portfolio projects, like ghost writing or content writing (a wise idea when you’re starting out!), then you want to be able to find some kind of metric to indicate success.

Example metrics to measure project success

  • How much traffic did the page or post get?
  • How long did people spend reading it, on average?
  • How many times was it shared?
  • What was the conversion rate for whatever the client was selling?
  • What was the client’s feedback or testimonial on the piece?
  • Did it get featured in another website or publication?

  • How many donors contributed to a non-profit?
  • How many people attended an event?
  • How much money was saved by cutting out redundant tools?
  • How many hours did you save by re-creating a process?
  • How many new potential buyers did you introduce to your client?

Think about the kind of outcome you want from these projects, and let your client know that you’re looking to measure these results as well.

Translate your work experience into measurable business results

The point is to translate these accomplishments into business value. If the average donor sends $30 to a given non-profit every year, then getting 25 donors to sign up translated into approximately $750 of additional income for that organization every year.

That’s significant.

Similarly, if you found a way to save 1.5 hours of time on a process that a professional or organization needs to spend on a recurring task (let’s say a weekly report), then you saved 6 hours per month that can now be spent on other things, like sales. If the person’s salary works out to $25 per hour, then you saved $150 per month and created room for additional value with whatever the freed-up time is put toward.

Here’s what it looks like when it all comes together:


A local non-profit needed to gain more donors to continue holding an annual event, but didn’t have the resources to expand its campaign.


You wrote the copy for their postcard campaign and helped out with their door-to-door campaign, and even developing a new slogan, too.


The organization gained 25 additional donors in this end of town, equivalent to $750 in additional donations for this campaign.

Here’s what it would look like as a bullet point on your resume: “Recruited 25 additional donors worth $750 in annual contributions through fundraising campaign.”


Every time you complete one of these projects or see measurable results, you should update your resume and your LinkedIn profile to reflect your new experience. 

Taking stock of your new work experience and planning next steps

This is a big part of how you break out of the unemployment cycle. Very rarely will someone hand you an opportunity out of thin air, and that’s why we’ve worked through identifying clients, creating a process for outreach, and systematizing how we extract value from every project to fill out that resume with substantial work experience.

By the end of this road map you should have:


A short list of skills you want to develop


A list of 20 prospective clients for outreach


A short list of  projects you’d like to take on


Contact information for every prospective client on your list


A messaging plan for LinkedIn and email outreach


1-3 work experience projects lined up or in the pipeline

Next up, we’re looking at how to build a portfolio website for yourself. You may want to focus building your work experience through these projects before tackling this next step, because it’s going to take you out of your comfort zone. It also helps to have more work experience under your belt before you make a website about it.

Affordability isn’t an issue for the next step in the road map, either—we cover a lot of free options for portfolio websites so that you can upgrade to the most professional options only when you’re ready (whether that’s a month or a year away).

Pro tip: Making a basic website isn’t actually all that hard, but it goes a long way toward setting you a head above the competition. My website put me ahead of 200 other applicants, ultimately positioning me to get the job that ended 9 months of unemployment.

It works. That’s why it’s worth the effort.