The job application process is brutal. If you want a job that’s even remotely interesting, you have to send out a million applications to positions that may have been filled 3 months ago. They ask for three years of experience for entry level positions. The salary stinks. And you wonder if you have any chance of breaking through the noise of thousands of other applicants. It’s disheartening, overwhelming, and time consuming. 

In my experience of working with people just like you, the job hunt and application process is one of the easiest areas to improve your Transformation Artistry. Why? Because most people aren’t willing to step outside their comfort zone or risk real failure to get (or create) a new job for themselves. 

For you, it all starts by saying “fuck it” to job applications.

After my firefighting days, I decided to give up my nomadic lifestyle and set up a home base in Austin, Texas. I had no idea how the hell I’d start over in a new city without any business experience, social base, or definite plans at the age of 28. I mean, most people I knew who were my age already had serious relationships and/or children, and had already established themselves in their career. As the days came for me to blindly move, doubts creeped in. 

How will I find a job? Do I even want a regular job?

Will I find a new group of friends?

Where am I going to live?

I had about $1,000 in cash, a rough plan for my first few days in Austin, and a willingness to fail.

The only person I knew in town was an old friend from high school. Luckily, she let me crash on her couch for the first two nights. It was great, but I had no idea what was next.

On my last night at her place, she got a text. It was from a friend of hers. The friend was jetting off to Thailand for a month, and looking for someone to take care of her dog and stay in her apartment for free.

“Yeah,” I said. “I’m her guy.”

Boom. Just like that, within 48 hours of moving to a new city, I had a place to stay for the next month. My next mission: find employment. I’d just finished watching “Silicon Valley” on HBO, and I was intrigued. Austin wasn’t the Silicon Valley, but it had a growing startup community of its own, and I wanted to jump in and see what it was all about. I wanted to make friends at work, do the happy hours, hook up with multiple women, start a tumultuous love triangle, and not have to worry about giant pine trees crashing down on my skull. The American Dream. 

I had plenty of excuses not to pursue that goal. I didn’t know anybody in the startup world, first of all. That’s a big one. And I didn’t have any office work experience. But I didn’t let that stop me. I just used every resource I had at my disposal and made it happen. Here’s how I did it…

Your 3-Month Plan to Get a Job with No Experience

Just a note: This is obviously just an account of one experience in one city, but in them you’ll discover a lot of actions and mindsets you can replicate in your own job-hunting, community-building or business creation endeavor.

Month 1

1. Reach Out to the Only Lead You Have

It was February 1st, and I only had a month of lead time in Thailand Girl’s apartment. I had to get to work. A couple months prior, a friend of mine connected me with his older brothers’ friend named Oliver who owned a real estate lending company . I had no interest in real estate, but I just wanted to connect. Maybe Jeff would know someone in some random little startup that I was interested in. Maybe we’d become friends. Maybe nothing would come of it. It doesn’t matter. In a situation like this, you just have to get a foot in the door—hell, a pinky toe will do if that’s all you can manage. If you can do that, the rest of your body will follow.

2. Expect (and Handle) Inevitable Rejection

Jeff didn’t respond for more than a week. In the meantime, my $1,000 was dwindling fast. I’d recently watched the Jim Carrey movie “Yes Man,” where his character is cursed to saying yes to every invitation, opportunity, or request that is presented to him. I figured the best way for me to get connected in a new city was to adopt that mindset: any time someone suggested we grab a beer, every time someone invited me to a party, every time someone invited me to the park—I said yes. And no, I did not become a victim of a serial killer (more on this in chapter 4). Instead, despite expanding my social circle, I became victim of a quickly-vanishing bank account.

I had to make something happen, and quick. If I didn’t, I’d run out of money and I’d be forced to leave town just as soon as I’d arrived, my tail between my legs in defeat.

5 job interviews came and went, all of them accompanied by a tidy and quick rejection email. 

“We appreciate you taking the time, however…”

Finally, on February 9th Jeff responded to my LinkedIn message and we met up for coffee. We talked about life, books, travel, and the fact that I was looking for a job in Austin. He said he’d help me figure something out, which got me fired up. There was no specific lead—just a vague idea that this guy would get me through the door somewhere.

I was confident I’d have a job within weeks, if not a couple of days! I celebrated my excitement by going out on 6th street, the heart of Austin’s live music and party scene, with some new friends. I wound up at a house party until 7am, and from there I caught an Uber back to the apartment wearing the same clothes I wore for the meeting with Jeff. I passed out with my phone ringer turned up, just in case I got a call from Jeff. I woke up in the late afternoon as the sun set and checked my phone. No missed calls, no texts.

Then three weeks went by and I still heard nothing.

Month 2

3. Follow Up (Respectfully)

February was coming to a close and Thailand Girl was flying back to America to reclaim her apartment. I had less than $600 left, so I sublet a room from somebody on Craigslist for $500. The sublease was only for the month of March, but I only had a couple boxes and an air mattress, so I was good to go. Suddenly, I had another thirty days of runway.

For the first few weeks of March, I tried to wade through the madness of South by Southwest, Austin’s music and tech festival. In the middle of this massive gathering of startups, I continued with the old fashioned route to finding a job: sending in applications and going on interviews.

That process was like a full-time job in itself. Except instead of yielding the cool results I was looking for—like money and personal connections—it only yielded more failed interviews and a dwindling timeframe to make this crazy experiment work.

Frustrated with the job hunt, I sent a follow-up email to Jeff:

Hey Jeff,

How are things going? SXSW was insane, can’t believe you Austinites have to deal with all of that every year!

I’ve been applying and interviewing for numerous jobs, but I’m finding it difficult to break into anything that I like.

Do you have any recommendations for people I could connect with to see about opportunities? I am very confident I can add value to a company with my leadership, team-focused work, and social skills. Just not sure exactly what that job looks like, to be honest.

Any help is greatly appreciated, many thanks for your time. Talk soon!

Bless my heart for that follow up. Looking back on it, I can see all kinds of mistakes: I basically left it up to Jeff to think up a job for me, I didn’t give him any ideas for the type of company I wanted to work with, and I didn’t specify what kind of opportunities I wanted.

There are a lot of problems with that message. But here’s something I did right:

I wrote it and sent it.

And that, my friend, makes all the difference in the world.

Perfection Is Your Enemy

You don’t need to connect with the perfect person, write the perfect cover letter, or craft the perfect follow up when you’re looking to connect with people in this way. You just need to do it. If you take too much time perfecting every step of the process, you’ll get stuck.

4. Get Specific About the Company You Want to Work For

It was late March now. Time was running out once again, and my money was dwindling even faster. I was laying on my air mattress as my Craigslist visa was about to expire, wondering if this whole “getting a job with no experience” plan was going to pan out. Maybe I could just make money off my podcast. I sat up and rubbed my sore shoulders. I had to get a real bed, a real place to stay and a real job—fast.

Suddenly, my phone lit up. It was a call from an Austin number.

“Alex, this is Andrew. Oliver told me about you and I wanted to reach out. Is now a good time?”

Turns out, Andrew was an executive for an Austin company, and he was one of the best-connected guys in the city. He took it upon himself to help people like me in need of a connection. He asked me what kind of job I was looking for.

“I’m not really sure right now. I know I want to work at a startup, and be part of a growing team, but I have no idea what I’d be doing exactly.”

There was a pause as he thought. “Tell you what. I can’t help you if you don’t know what exactly you need help with. So why don’t you take some time to really think about what you’re looking for and get back to me. I’ll be happy to help you then.”

Did I just blow my best opportunity of this whole process?

Andrew was right: I had to get specific about what I wanted—more specific than “I want to work at a startup with lots of happy hours and cute girls.” Turns out, that described damn near every company in Austin. And it wasn’t enough to say I didn’t want “a typical 9-to-5” because, again, jobs like that were abundant.

I thought back. I re-read my follow-up message to Jeff. I retraced my steps across the high deserts of Arizona, cutting down trees with the fire crew. I contemplated my strengths: my social skills, my openness, and my leadership. I thought about all the job interviews I’d been on so far. And it hit me: sales. I’d make a hell of a salesman.

I went on LinkedIn and found every mutual connection I had with Andrew and Jeff, sniffing out someone they could introduce me to. Finally, I found someone who worked for a company called OutboundEngine, a marketing automation company in Austin. They looked like exactly the type of fast-paced startup I was looking for. But time was dwindling.

Month 3

5. Use Your New Connections to Get in the Door

On a Thursday in early April, I was on borrowed time with my sublet and running on credit card fumes. As I was driving to the local store one morning, I passed a moving company that had a “Now Hiring” sign out front. Manual labor is always good for being hired quickly and this was no different. 

I started Monday. 

The next day, I got antsy and applied for a sales job without contacting Jeff or Andrew first. OutboundEngine rejected me so fast I wondered if they’d even waited for me to hit “send” on my application.

I reached out to Jeff and told him what happened.

“It’s pretty frustrating: I finally found a company I’m interested in and a job that I’d be good at, and I couldn’t even get a conversation with them.”

“You said the company was OutboundEngine, right?”


Jeff thought for a moment. “Actually, I know their President of Sales. Let me connect you with him.”

Suddenly, I had completely circumvented the entire application process and I was in the door for an interview. All because of the connections I’d made.

I gotta tell you: when that happens, it’s one of the most badass feelings of your life.

6. Prepare Like Your Life Depends on it

But there was still work to be done. I couldn’t let another opportunity pass me by like when I’d been on the call with Andrew and had no idea what I even wanted from him. I spent hours preparing for the interview—I learned everything I could about the company and the people I’d be speaking with.

When I walked through the door, I knew I had nothing to be nervous about. Not because I was guaranteed to get the job—that was far from certain. But because I’d done everything I possibly could to make this a successful interview. That confidence carried through the entire conversation.

I got the job.

Within days of getting the offer, I found a more permanent $500 room to rent in a house with two girls and a giant Saint Bernard that slobbered over everything. No more bouncing around apartments hoping I’d stumble on a living situation that would work for me.


  • Reach Out to the Only Lead You Have
  • Expect (and Handle) Inevitable Rejection
  • Follow Up (Respectfully)
  • Get Specific About the Company You Want to Work For
  • Use Your New Connections to Get in the Door
  • Prepare Like Your Life Depends on it

Just Get Your Foot in the Door

At OutboundEngine, I found a lot of what I was looking for: a cool startup with happy hours, cute girls, fun people, and a lot of challenges. I didn’t stay there forever, but it introduced me to so many people and amazing experiences in a brand new city that I almost can’t believe it. In other words, getting that first job was an exercise in getting my foot in the door of an entire city.

That’s all the job hunting process is: getting you pinky toe through the door, then your foot, then your entire ass (both cheeks)—especially if you’re trying to get a job with no experience. Because here’s the thing: your next job won’t be your last job. That’s not a sign of failure any more than applying for a job and not getting it is a sign of failure. It’s a sign of growth. It’s a sign that you’re a Transformation Artist.

After I got the job at OutboundEngine, I had no intentions of staying there forever any more than I had intensions of waking up in a house with two roommates and a Saint Bernard slobbering on my face very morning for the rest of my life. That’s just where I was at that moment. That was the phase of growth I had entered.

And when you look at things from that lens—each move you make, and each achievement you reach is just the foot in the door to the next thing—it makes the imperfections of the moment more tolerable and (dare I say it?) even enjoyable.

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About The Author

Madeline Carpenter is the founder of Market ‘Til You Make It. When she’s not serving her clients, she geeks out on board games, cider, and challenging her friends to top her awesome karaoke skills. She calls Bloomington, Minnesota home.