How I Went From Underemployed Waitress to the top 1% of Millennials in 3 Months

Blog Series, Community, GenDIY, Leadership

GenDIY is all about people carving out unique pathways to careers they love. As part of the project, we’ve talked a lot about the importance of charting your own course, but not exactly what that looks like. That’s why I’m excited to share this blog by Lauren Holliday that first appeared on Medium. She details, step-by-step and complete with millennial color commentary (#FMLs and all), how she took control of her journey from dropping out of college to beginning her career.

Her story exemplifies the entrepreneurial mindset, creativity, and do-it-yourself spirit of GenDIY. Or more simply put, the GenDIY imperative of getting your S*!% together. From insights on how she skilled up, built a portfolio, weighed choices like taking online classes and how she uses tools like Google Spreadsheet, this blog is quintessentially GenDIY.

Lauren Holliday

“I’ve missed more than 9,000 shots in my career. I’ve lost almost 300 games. 26 times, I’ve been trusted to take the game winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.”

— Michael Jordan

“All the best things that happened to me happened after I was rejected. I knew the power of getting past no.” 

— Barbara Corcoran


I scour Reddit A LOT. One subreddit I thoroughly enjoy engaging in is “r/findapath.” In this subreddit, young people are redundantly asking three formations of the following questions:

  • How do I get a job (I enjoy) that gets me out of my parents’ house?
  • How do I gain experience when I have no time?
  • Which career should I choose?

These are really important questions, and it got me thinking about how I could help my underemployed peers.

Truth is, there are a lot of different ways to get a well-paying job you love. Most job hunting advice comes from people our parents’ age — “career experts” — who are far from “in your shoes.” Some of their tips work in one instance or another. Others just don’t.

Let me tell you a bit about me.

I’m a Millennial, who not too long ago, was waiting tables 40+ hours per week in my hometown. I had just dropped out of college because I couldn’t support myself and was forced to move in with my dad. Talk about a shitty situation.

Flash forward six months.

In this short amount of time (that felt like dragged on forever) I negotiated a $72,000 salaried marketing director position and $3,000 in relocation assistance, which moved me to Boston, the land of opportunities.

(Since then, I’ve gone out on my own, and today, I’m in the top one percent of millennials.)

Of course all of my friends wanted to know one thing — How I pulled this off.

Important Insight: These are the high level bullet points. The big picture of what I would do if I woke up one morning in my former unhappy and underemployed self’s cute flip flops and long dresses. I had no contacts. I had little professional experience. Just a roof over my head, free meals and a good head on my shoulders.

With that being said, this is my story of what I would do to move out of my pop’s house and on with a career that isn’t less than what I have to offer.


I would aim to become a full stack marketer.

Full-stack derives from web developers, who can do a project from start to finish without assistance because they know front end and backend programming languages.

unicornFull-stack developers are purple unicorns, meaning they are extremely difficult to find. Similarly, this is the case with marketers — especially for marketers whose clients are small businesses and startups.

The marketing stack is a bit different though.

If you’re a full-stack marketer you can complete everything your client needs from start to finish. A purple marketing unicorn will be able to easily produce successful campaigns at every stage of the marketing funnel.

This means more money because the majority of marketers specialize in things like social media and SEO, which, in my opinion, is a huge handicap.

There really isn’t anything difficult about gaining experience when you think different. What I am about to present to you is a tried and proven universal framework for gaining experience, landing jobs and getting paid.

Here’s How I Would Do It

STEP 1: Get just one project that will add a quality piece to my portfolio. Then get just one more project that will expand my skill set.

STEP 2: Design solutions’ packages, and document my procedure for it. I’d start charging clients for my service immediately upon completion of Step 1 and would focus on one paid project at time.

STEP 3: Finally, I’d design my digital footprint then I would start twerking the job hunt, i.e. marketing myself.


Before I start, I have to make a decision, which sucks, because I’m so indecisive I can’t even make a bagel selection in under 15 minutes most of the time. #FML

While I have already made the executive decision to generalize and not specialize in the digital marketing industry, I still need to decide if/how I should build my skills and/or gain experience.

Here’s my options:

Option 1: I can learn in-demand marketing skills by registering in
online classes through websites, such as Treehouse or Fizzle.

Con: Another class is not going to provide me with real-world experience. Meaning that another class will not increase my earning potential, which is at $0 right now. Oh, and it would most likely cost me money, which I am not all about at this moment in time.

Option 2: Or I can gain real-world experience by utilizing
my family and friends’ businesses.

Pro: I get real-world experience right from the get-go because it requires me to figure out, on my own, without being told, what to do. Far more valuable.

Con: I won’t get paid for my time… yet.

Option 3: A hybrid of No. 1 and No. 2. Learn what I need to do by researching and reading online while simultaneously building out the real-world project (a WordPress website) for my friend or family member.

Pro: I get real-world experience right from the get-go while simultaneously developing valuable skills.

Con: I won’t get paid for my time… yet.

Oh, how I hate making decisions! But ultimately I would opt for option three. It offers me immediate leverage and reaps the biggest rewards.

And the winner is… Option No. 3!


Now, the first thing is that it’s 99.9 percent likely I won’t get a perfect first gig, and it probably definitely will not be paid because I cannot prove my competencies and/or I may not even be really good at building WordPress websites or marketing them yet.

I would essentially fake it ‘til I made it.

Instead of overwhelming myself looking at the big picture, which inevitably would stress me out and paralyze me, I will break down my tasks into phases. Actionable chunks. Then proceed forward.

Actionable Phases

Four phases. Six months.

(This could be done in much fewer than 6 months, but for the purpose of not biting off more than you can chew, I recommend giving yourself 6 months.)

Completing the first two phases would be my immediate goal and my sole focus to start.

If you need help finding a project, sign up for,
which provides young people with freelance projects to gain experience.

My father owns two dry cleaners. I would ask him to allow me to create a simple WordPress website for his local business because every business needs to have an online presence. His digital marketing is seriously lacking so he would love my idea.

This one WordPress website I will create for my dad will earn me:

  • Identity capital (proven professional experience)
  • A recent work sample
  • A repurposable product that is easy to resell for half the amount of work the next time around

Let’s recap. I really like this product offering because:

  • It’s one that’s in-demand, and therefore easy to sell
  • I can easily create upsells, building returning customers, allowing me to:
  • Make more money
  • Build additional, complementary skills, again which would make me more money
  • I can easily create a vertical market toolkit, allowing me to earn double and do less work

Only after I complete Phases 1 and 2 would I move onto Phases 3 and 4.

These phases are when I would start charging for my services — immediately upon my dad’s satisfaction with his new WordPress website — and then begin designing my digital footprint.

Phases 3 and 4 will set the stage for my professional life in which I do enjoyable, well-paid work and move out of my rents’ place ASAP.


Phase 1: Build my skills. Gain real-world experience.

Begin with WordPress.

I would learn how to create a professional WordPress website and document the procedure for doing it so I could streamline the process.

The WordPress site would include:

  • 5 SEO-optimized pages (Home, About (Our Story, Team), Services or Products and Contact)
  • 1 blog
  • Google Map with location and directions
  • Social share buttons
  • Header and footer
  • Google Analytics website tracking
  • 2 forms: 1 newsletter opt-in form (This requires me to create a FREE Mailchimp account) and 1 basic contact form

Note: SEO-optimized means I wrote: Page titles, descriptions and focus keywords, based on my keyword research.

“It’s cheap. It’s easy to do. And it can take less than 20 minutes to set up.
Yet more than half of all small businesses still don’t have a website.”— Inc article

The skills I gained from this project include:

  • WordPress
  • SEO
  • Web design
  • Copywriting
  • Google Analytics
  • Keyword research

Upon completion of my first project, I will begin charging.

Phase 2: Develop more skills. Create more product offerings.

I would utilize my father’s dry cleaners yet again so I could:

  • Gain more in-demand skills
  • Increase my earning potential

First, I would research the most effective content marketing strategies, tying the best ones together to create uniquely valuable strategies’ templates that I could easily customize for small businesses in various industries.

The strategy I developed is a launch strategy — a comprehensive go-to market (for startups) or digital marketing strategy (for small businesses).

I would market my father’s new website, making it easily discoverable by his new and current customers.

But the main focus of Phase 2 is actually to build rapport and trust with professionals in the online marketing world. I would continue to develop my skills and document the results of my efforts.

I’d position myself as their go-to full-stack marketer — their one-stop shop for business development — a trusted, passionate and highly knowledgeable one at that.

As part of this stage, I’d introduce three additional solution offerings into the storyline. These products would work to enhance the value of the website I initially created and build complementary skills that allow me to earn more money and land a higher paying career.

There are logical steps that exist between where a startup or small business is now and where they want to go.

It is my responsibility to help each client move closer to their desired end result with the services I provide and sell to them.

The WordPress website I sell after I successfully create my father’s will be my first product offering.

The launch strategy I wrote in this phase will address the remaining biggest roadblocks of my clients. It would recommend that they hire me to customize and execute an inbound marketing strategy as the ideal solution for these roadblocks.

The launch strategy includes the following items which can be sold separately:

    • 1 blog strategy or editorial calendar
    • 1 social media strategy
    • 1 SEO strategy
    • 1 email marketing strategy

Phase 3: Showcase my newly proven skills.

This phase only comes after I’ve executed on the above strategies for my father’s website, measuring the results/statistics for 90 days.

It would provide me with proven solutions to my potential clients’ problems, showing them how I took my father’s site from page nothing to Google page one.

I would purchase a domain name and create a WordPress website for myself to showcase my amazing work experience in the form of screenshots, videos, whatever. Everything.

FACT: 56% of all hiring managers are more impressed by a candidate’s personal website than any other
personal branding tool — however, only 7% of job seekers actually have a personal website.

Depending on what resources I used, it would probably cost me less than or around $100 if I bought a premium theme, which I would most definitely do.

Oh yeah, I’d get business cards and brochures made ASAP from somewhere cool online.

Phase 4: Make it rain on them jerks who didn’t hire you.


Remember those business cards and brochures I literally just mentioned?

I would take them and place them at my dad’s storefront, where his customers could browse while they wait to pick up their clothes. Not only would I try to sell them on my services, but I’d also educate them on the Internet and how it has changed marketing.

I’d write a blog post for my website, which I could repurpose as a handout at my dad’s store, titled: How to Increase Revenue for Your Local Small Business.

This is essentially the entire master plan. It’s what I would do if I only had a roof over my head, free meals and a good head on my shoulders.

Costs so far…

Phase 1 and 2 literally only cost me my time and my father’s investment in his business.

For Phase 1, I would tell my father he needed to provide money for:

Website Hosting:

  • A recurring monthly fee of $5 or less OR
  • One-time annual fee of less than $100

Note: Explain website hosting to Dad/Mom like this… Website hosting is like rent for your store — except it’s online rent. You must pay to have a space online just as you have to pay a fee for your brick-and-mortar store.

Domain Name:


Premium Theme:

  • Between $30 to $60 on Envato’s Themeforest — Make sure you are looking at WORDPRESS themes

Graphics (You really should include a photo/graphic on each page)


  • Time cost on my part because I would need to take photos of every team member for the about page
  • I would take a few creative photos of the storefront, staff and customers


  • Another time suck on my part
  • I would gather testimonials from my father’s clients or ask my father to do it (which he probably wouldn’t; therefore I would have to)

Spend so far:

Me: $0 and a few hours

Dad: $100 — let’s say this number to be modest

I would ask my father for $125 to be safe, and explain the above costs to him. Frame this as an investment in his business.

Phase 3 and 4 require virtual cash out of my own PayPal because I could not talk my father into purchasing my website supplies. (But I bet some of you will succeed at this task!)

So Phase 3 would cost me the same as my dad’s website. It may actually be less because of this Google search I did for student discounts on web hosting, which is the biggest cost in the long run since its a recurring monthly fee.

For Phase 4, I would also look for student discounts on, and discover that the company, which produces beautifully luxurious business cards, provides lower rates for students on business cards and other marketing materials, such as brochures.

Since I am pretty good at design, and I want to see a high return on investment (ROI) I would invest in purchasing a unique and creative brochure and business card template to help me stand out from other freelancers.

To play it safe, I would guesstimate this costing me about $100 or less in total.

What IF I didn’t get any customers after all this work?!

Phases 1–3 would need to be complete in order to land my first client(s). That would be my immediate goal and only initial focus.

It’s HIGHLY unlikely that my efforts would go without even one sale, especially since a lot of people know and TRUST my dad, but what if people didn’t?

After completion of Phase 4, while I was waiting on my marketing materials, I would be proactive and open a spreadsheet in Google Drive and label it “Local Dry Cleaners.”


Next, I would create 10 columns, titled:

Business name
Phone number
Date called
Date visited
Spoke to (person’s name)
Website in place? (Y/N)

If yes, website grade, which includes:

  • Digital Marketing in place? (Y/N)
  • Are they listed on local directories for small businesses?
  • Do they have verified and ACTIVE social media accounts that are right for its target audience?

If they’re active, are they actually engaging customers?

Notes (Anything about my interaction with the person I spoke to that may be helpful in selling them my product)


Then, I would:

  1. Search Google for the following queries: “Dry cleaners near me” or “local dry cleaners” or “dry cleaners [insert city name nearest you]”
  2. Search Yelp for local dry cleaners to see which ones had VERIFIED local listings. If they do not have a listing then I can upsell them on submitting their website (if they have one or after I create one for them) to local directories.
  3. Search Google Maps on my phone for “dry cleaners” because this is an easy way to walk into a local dry cleaners and strike up a conversation…“So I’m looking for a local dry cleaners, but you don’t come up on my Google Maps. Do you know how many customers you could be missing out on because of this?”

I would spend one to two hours inputting all of the data I found from the three tactics above into my soon-to-make-me-money spreadsheet.

Finally, I would email then call.

I would email the local site directory and website grader reports to my prospects. Give them a day to follow up, and then call.

Of course, I would try to discover the owner’s name because it is better to ask for “Tim” than “Holliday Cleaners’ store owner” (that just usually means it’s a sales call, and I know my dad never answers those so I would refrain from sounding like a sales woman).

Customer Value

Let’s look at some hypothetical numbers.

This is what I would charge for my first few websites I built and my first few strategies I executed.


**Customers pay an additional cost for resources, including: website hosting, domain name and theme purchase. The only resource I would foot the bill for is the graphics, which I would build into my cost structure.**

Not only am I looking at a quick and easy $500 and $1000 one-time payment, but I am also looking at potential recurring revenue, which I’ll very likely get because it’s affordable and small businesses don’t have the time and/or do not want to handle this themselves.

JOB SECURITY: Multiple Repeat Clients Vs. One Full Time Job

By now, I have money in the bank, happy clients a.k.a killer references, loads of proven experience, amazing soft skills, such as: innovative, hard working and creative and a gorgeous showcasing of all of this via my website.

Finally, I am in control of my destiny, and so like anyone with valuable experience, I have options! (Woohoo!)

Option 1: I could apply (and land) a full-time job.

Option 2: I could keep freelancing,

  • On a project-by-project basis,
  • by keeping a few clients on retainers OR
  • work part-time for two companies.

All are good and viable options, and in fact, I’d pick all of the above. Basically, I would freelance, picking my favorite projects to work on 80% of the time, and the other 20% of the time, I would dedicate to the job hunt.

“Sometimes life hits you in the head with a brick. Don’t lose faith. I’m convinced that the only thing that kept me going was that I loved what I did. You’ve got to find what you love. And that is as true for your work as it is for your lovers. Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do. If you haven’t found it yet, keep looking. Don’t settle. As with all matters of the heart, you’ll know when you find it. And, like any great relationship, it just gets better and better as the years roll on. So keep looking until you find it. Don’t settle.”
-Steve Jobs, Stanford Commencement Speech

Don’t settle, but also, don’t take Jobs’ quote the wrong way. It takes time to find the perfect career, if there is such a thing. You have to take on these less exciting gigs before you make it to Oz. If you don’t then you may never get there.

Keep testing your different career paths and skillsets by freelancing. Apply to jobs for interview experience, but if it’s a job you won’t be happy at or don’t feel right about (assuming you’re making money freelancing) then don’t accept the offer — even if it is for more money.

Don’t settle for a full-time job you hate. Hack freelancing until you know what it is that you want out of a career, which may not turn out to be an actual full-time, in-office gig.

Don’t settle. Experiment. Diversify. Keep testing until you find what works for you. It won’t be long until you find it… if you listen to my advice.

For more on GenDIY, check out:

Lauren Holliday is the Founder of Freelanship. Follow her on Twitter, @LaurenHolliday_