The Emotional Journey of Job Hunting in San Francisco

January 10, 2018

This is a sequel to 6 Things I wish I knew about Job Hunting in San Francisco. It’s been 1.5 years since the article and I am humbled to still receive messages from people that have found it useful.

So many strangers and new friends have reached out seeking advice. Through these messages, I realized that it is the inner demons that need reassuring when one is lost. People needed words of comfort not practical advice, they wanted to hear my emotional journey, and to hear that I too, once felt as discouraged but have now succeeded.

So I am here to share my emotional journey. I may not have been ready to be so vulnerable until now. Because I really did almost give up. I really did feel so stressed that I could not sleep and wake up each morning drowning in self-doubt.

At the time of the last article, I joined Lending Club. 5 weeks after writing, I was laid off again.

Here’s a recap:

After graduating in 2015, I optimistically moved to San Francisco because it was the central hub for tech and entrepreneurship, and the best place I could shape myself to be who I wanted to become. What I faced was 2 lay-offs in under a year due to a startup going under and a CEO getting fired. These events tested what I was made of and put a microscope on what is supposedly “celebrated” (but isn’t actually) in Silicon Valley: failure.

Since no one else I know has had the blessing of getting laid off every 5 months within a year and having the opportunity to (need to) interview and talk to over 100 companies in the bay area, I hope that you can take something away from what I have learned.

What doesn’t kill you makes you stronger

I have always been a persistent person and perhaps confident to a fault. It is not easy for me to feel rock bottom.

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Needs and priorities at startups are always changing so I have seen every kind of rejection email.


Budget Re-evaluation

A bit late on the introduction game

Email after warm outreach

Finding a fit was important to me as I wrote in my last article. I was patient and enjoyed the process of learning about different companies and different roles.

There was only one moment during these job hunts that almost became the final straw. I almost packed my bags and flew home to Ottawa.

The most dejected I have ever felt in my life was when I received a rescinded verbal offer from what I thought was my dream position at my dream company, after 2 months job hunting.

I am an avid traveler having backpacked 30 countries in the last 4 years, an extreme extrovert that loves making friends everywhere I go, and a preacher of global tolerance so I lived and breathed Couchsurfing’s mission statement:

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Couchsurfing was restructuring and having a somewhat identity crisis. They were not hiring. I got a warm intro to the Head of Product and presented myself as “the Jill of all trades who gets shit done”.

After an initial coffee chat and before an official interview, I sent them my ideas on everything I learned during this chat. Check it out here: Brainstorm doc

And so I got my first piece of homework:

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For the first onsite interview, I presented: Local Advice

I went above and beyond to do research on how different forums are managed. I talked to my connections at different companies that managed forums and supplemented the presentation with this doc: Forum Moderation at other Companies

I was then sent home with some Financial Analysis homework and to write what I had presented in a product spec on Forum Moderation.

I went in for a second onsite and walked through a financial analysis on payments failure (cannot share due to NDA) and a 9 page detailed product spec: Forum Moderation Product Spec

The team was impressed. I was now sent home with a SQL assignment.

So I completed it — with some help from online classes and my ex-manager from Vouch.

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Somewhere in this process I also sent in references.

Finally after the third onsite, a 3 week interviewing process, and 40+ hours spent on assignments, I got an offer over the phone and an email asking me for visa requirements.

Then silence for 2 days.

Then this email:

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That day I cried more than I remember ever crying. It was not for the job. It was for the hope after a verbal offer. It was for the heartbreak after pouring my heart and soul and giving 100%. It was wanting something so bad, trying so hard, and thinking I definitely had more heart than anyone else they could bring on to the team. I was ashamed I could not get my life together and find a way to stay in San Francisco. My ego also hurt.

I felt cheated. I felt like life was unfair. I cried “Why me.”

In my desperation and as a last shot, I put aside all that pride. At 3 am, unable to sleep or to stop crying, I wrote the Couchsurfing leadership a letter. The only thing they can do is still say no. Here it is: CS Cover Letter

It was in vain and they did not change their mind.

And stronger I got…

I learned 2 valuable lessons through this rejection.

The most valuable things in the world is the support of friends and family

At this point I really did feel like I had nothing left. Who was I, a fresh grad deemed to have high potential but unable to land a job? Without a job I would be unable to support myself, unable live the life I want, unable to move on in other aspects of my life.

My best friend in Toronto listened to me moan and cry on the phone for hours. My friend in San Francisco left his mom at dinner, came over and held me as I cried until 1am.

I had already told my mom that I got an offer only to tell her 2 days later in whimpers that it was rescinded. Later in the day I got this email:

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I cried more.

It is in the darkest of times that this kind of unconditional love means the most.

Although I was not in financial desperation, the biggest fear is that I will run out of money before I find another job. My friends and family understood that I needed the financial pillow to keep my head high and focused on the goal of staying in San Francisco.

Friends, 23–25 year olds that have been working only a year or two themselves and even those saving up for grad school, offered to transfer me money. One gave me his credit card to use for emergency. I lived out the true meaning of “what’s mine is yours and what’s yours is mine” — a phrase I use to describe my best friendships.

For some crazy reason my friends with likely meager savings themselves believed in my abilities to pay them back. They believed in me when I did not. Even more touching was that they believed I deserved that kind of friendship.

It was through them that I remembered the little voice which urges you to just try one more time.

However you maintain your financial livelihood does not define you. The people you keep and the people that you manage to keep in your life do.

  1. You are your most valuable asset.

Continue improving yourself and learning through the job hunting process.

I interviewed for everything from Product Manager to Digital Marketing to Sales to Business Operations to Data Analyst. And I learned a lot about every role and how it’s different at different companies. I questioned the purpose and existence each company’s business as well as my own priorities and values.

I took 5 online SQL classes in one week after claiming I had SQL knowledge. I learned how to write Product Specs. I followed growth forums. I joined data meet-ups. I took numerous classes I found on Eventbrite and continued to read one book biweekly.

Today, although my main role is Business Development, I used my previous analytics experience to build out reporting tools and CRM processes for the entire team. I coded web scrapers to help with lead generation. I am able to take on more responsibility because of the skills I learned when looking for a job.

You are always a work in progress. Having more skills and more knowledge will never hurt you in the future.

Remember if you are qualified, or over qualified, and you put in so much that rejection breaks your heart— it is their loss.

There are infinite places to build out your dreams as long as what lies within you is passion, competency, and an eagerness and curiosity to learn.

In Conclusion

I have been at Wish for over a year now. I know I ended up in the best place possible and am exactly where I should be and want to be right now. Remember, your happy ending is up to you. I hope you find what you’re looking for as well!

For all the job hunters out there, Wish is hiring! : Check out the Careers Here!

Message me for a referral!

Would love to hear your story and connect — find me anywhere online @ivyxvine