El Camino Del Trabajo

“The secret of getting ahead is getting started.” -Mark Twain

On July 3rd, 2018 while sitting in a listless hotel in the coastal hamlet of Exmouth, I signed a piece of paper. Yet, this wasn’t just any piece of paper, but a job offer.

And this wasn’t just any job offer, but was my first full-time role in 4 years.

After 1,460 days, 500 Uber Eats deliveries, 160+ applications, ~63 rejection emails, 7 consulting projects, 4 offers, and 1 contract job, I joined the team of an ambitious Seattle-based startup with a role on their in-house marketing team.

What had felt like 6 months of heads down job hunting had actually been nearly 3 years yearning to be part of a team, not just a freelancer, consultant, or temp at a slothy conglomerate. For those who know me well know that patience is not my strong hand.

Bizarre enough, the job has checked nearly all the boxes of the ideal dream role I had been holding out for: high impact, working with sharp & ambitious marketers, all with a digital marketing frame.

Those who know me also know that I’m an hopeless optimist.

Like a PI, I believed obsessive research and grit would get me incrementally closer to the right role and team and in the process help me reach some level of “career enlightenment” where I finally would be doing what I was truly passionate about, marketing.

And I’ve found it.

And am still finding it. Like meditation, it has become less about the outcome and more about the process where along the way I’m becoming a world-class marketer.

“Most people never realize that 80% of the work is done before you step in a room.” -Ramit Sethi

Like a fly stuck in amber, each internship, project, book, and gig compounds and I find myself chiseling away at the marketing bust, slowly becoming the master I aspire to be.

Thus, I’m writing this for 2 reasons: 1) to share the 3 biggest lessons learned along the way, and 2) to part the 2 most valuable tricks I learned along the way.


Lessons Learned

#1-Each Has Their Own Catch 22

Catch 22: a dilemma or difficult circumstance from which there is no escape because of mutually conflicting or dependent conditions.

If you’re a hungry human and want the best for yourself, you’ll find yourself in this position: seeking out roles that are a cut above what you are on-paper qualified for. Albeit a non-linear career path, I had earned the title of Program Manager at my recent contract job and believed I could parlay this to get a Marketing Manager role.

Little did I know that these roles often entail 5+ years of tenured experience, leaving me with a limp *resume* in my hand. “But wait! I’ve been a manager!” I imagined myself bellowing as the bus drove off while I stood there soaking in the rain gripping a soggy resume.

Ultimately, there became ways to work around this but the irony was apparent: believing you have the full potential and gumption to don a role, but lacking the hard skills.

That said, my advice is still the same though: never settle for less. Dream big and pursue it with grit. There are plenty of smaller companies that will gladly take a leap of faith on your high potential.

#2-The Antithesis of Job Security is Insecurity

In a culture where you’re often judged by 1) the status of your significant other and 2) your job, it becomes apparent the quiet disdain that quickly settles in when you’re not with a company like a NFL free agent without a contract.

Explaining to other people you’re unemployed when they ask “what do you do?” is a sure shot conversation killer and not only knocks the wind out of the chat , but also leaves you asking “so what am I doing with my life?”

The answer is more simple than you think: be an interesting person. Start a side project (a friend in a similar position instituted a small cryptocurrency mining operation), freelance, or start a blog.

Do SOMETHING! Pursue what excites you, ideally in a professional lens, and get comfortable including it in your elevator pitch (ex. “I’m between jobs so I devote 15 hours a week to photography. I take headshots of friends, past co-workers, and mentors so to start building my portfolio while staying in touch with business contacts.”)

#3-Learn negotiating before anything else

Roger Dawson once said “there is no quicker way to make money than when you’re negotiating. Think about it: by negotiating for a mere $6000 more in salary it could take you at most 6 minutes and that converted to an hourly comes out to $60,000.


Never underestimate the power of negotiating and tell yourself you “don’t feel like it” because you don’t want to come off looking like an ass. If anything, negotiating is a sport, a game of tennis if you will, and both sides are expected to volley so to 1) reach the fairest outcome and 2) have the best match.

While sending your applications down the proverbial black hole, buy a negotiation book and read it cover-to-cover over 30 days. I recommend Roger’s The Secrets of Power Negotiating or Malhotra and Bazerman’s Negotiation Genius. Ramit Seth also is a great thought leader on the subject (case in point, check out “The Briefcase Technique” to find out).

If possible, “steal like an artist” and get 3 different perspectives (from books, blogs, or courses) so you can blend it into a cocktail that’s perfect for your communication style and comfort level.


2 Job Hunting Tricks

The Trifecta Technique

We all think it but few say it: completing job apps is hell and feels worthless. I talked with Seattle’s leading headhunter, Gina Peckman, and asked “is it worth the time?”

Her response?

An unequivocal “yes.” It puts you into the company’s system and makes you trackable. That said, the application will be the least important part of your strategy.

Thus, I recommend following what I call the Trifecta Technique. After finding the position, do all 3 of the following:

  1. Submit your resume (just get it out of the way)
  2. Connect with the co’s in-house recruiters on LinkedIn and send them a personal message introducing yourself
  3. Flex your network and find 2nd or 3rd connections to ask if they can make an intro to the hiring manager

Wash, rinse, repeat and you will start growing your professional network while gaining quality momentum.


Tony Robbins says you can tell the quality of your life by the quality of your questions. I agree wholeheartedly and in job hunting, it’s no different.

If you can ask the right question at each step of the interview, you can differentiate yourself from the 100+ other candidates and hence, be noticed.

After getting into the interview loop, always ask the following (divided into different stages in the process):

Pre-Interview #1

• “I like to do an assignment during the interview series to give you an idea of 1) the quality of work I can produce and 2) see what our work dynamic would be like. Do you have a 1-2 hour assignment you could send?”

Closing of Interview #1 (i.e. phone interview)

• “Based on what you learned about me today, would you recommend me for this position?”

In response to “sorry you didn’t get it” (phone call or email)

• “I think I’d really like this role and working with your team. I’d love for you to mentor me so if a position opens up in the future, I’m well positioned with the right skills and experience. Would this be possible?”

In response to “sorry you didn’t get it” (email)

• “Is there anyone who you recommend I should meet who knows of open positions? In or outside the co.”

If you read between the lines, each question possessed it’s own power and either 1) said something very positive about you (i.e. you’re ambitious and no average candidate) or 2) lead you to a new door of opportunity.

You have nothing to lose by asking, so why not balls up and try?

NOTE: feel free to copy & paste these.



Job hunting can be a lonely journey where you can feel no one really cares to help. Yes, no one will hand you a job, but plenty of people will provide advice, connections, and support that in the long term is worth 10x more than the next role you fill.

Along the way I couldn’t stop thinking of how I wished there was a single source acting as my job search buddha, shepherding me with words of encouragement, insights, and back rubs to the job of my dreams.

And now that I’ve taken the journey (and could again in the future), I hope I can be the Sherpa for anyone who is currently in the market and feeling lost.

If you’d like to chat more, please reach out via the contact form and I’d be happy to help in any way possible, whether with sharing my network or rendering more tools, tips, and practices along “the walk.”



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