2 (incredible) years at Headout

We have a very interesting tradition at Headout for every work anniversary – a speech in front of the entire office followed by a roast with a bunch of questions, ending with a cake and a bottle of bubbly. I have very conveniently been dodging this tradition for my past 2 work anniversaries, so here’s me attempting to put down the absolute pleasure I’ve had over the last 600 working days at one of the very best companies in the world.

I joined Headout after quitting 2 jobs in a span of a year and freelancing for the next 4 months. I’ve always loved working and trying my hands at something new. To put that to perspective – I did an internship for 2 months every year through my graduation and post-graduation (that’s 6 internships over 5 years). Through the course of these 6 internships, I’d learned one thing – I had to love my job to be able to put my best foot forward. I had to be head over heels passionate and intrinsically love what I am doing to be able to devote myself entirely to the work at hand.

When I came across Headout on LinkedIn, I had never heard of the company. They were looking for a travel writer, and at the time and I was freelancing for a few other travel portals. Having always had an inclination for the travel industry, the thought of travel writing as a full-time job sounded ideal, almost dreamy.

The Glassdoor reviews for Headout at the time were a mixed bunch – a few hated it and the others absolutely loved it. I chose to trust love over hate (no regrets). The company had fewer than 50 employees, but I had worked with a company that had over 2000 employees and another with just about 6 employees – the number of people in a company clearly didn’t make a difference. In less than a month, I was in a new city with a new job and a meek prayer in my head, hoping for this job to be the one. Turns out it did!

I started as a writer in the content marketing team – writing about 30 blogs a month. Venice was one of the first cities I worked on, and at one point, I knew the streets of Venice by heart. I had seen so much of the city via Google Maps, I didn’t think I needed to visit the city anymore. But, I loved my job. I was writing about far off places, virtually traveling the world – finding a nook and pouring my research into lucrative words that inspired people to pack their bags and leave!

In 8 months, I had my first promotion and an urge to do more than just writing. That’s the thing about a place like Headout. It gives you the absolute freedom to find a problem and solve it the way you can/want. All that matters is that you fix it in the end. Decision making and problem-solving is not limited to the C-suite employees. If you’re a fresher right out of college who has the caliber to lead a project, you will be given the opportunity to do so at Headout. And, that’s what makes all the difference.

I was put on a customer retention project around June 2019. With absolutely no clue about email marketing, retention and customer relationship management, I was put on this project simply because I had mentioned my interest in expanding my horizons and venturing outside of the content marketing zone during my quarterly review. Though this was an interim role to launch the process while a dedicated team was being put together, leaving the project in my hands when I had absolutely no prior experience was a huge risk. My extremely supportive boss, however, pulled me into it and pulled me through it as well! Forever indebted to you, Parag Jain.

2 years may not seem like much, but Headout has been a journey I thank my stars for! I’m no expert, but here are some things I’ve learned along the way.

  • Never settle: If you don’t enjoy what you do, don’t stop until you find your version of Headout. Once you find your Headout, don’t settle then either. Evolve and always keep the learning going.
  • Always find more things to do: I’m not sure how this pans out in a corporate, but doing more than what your job role states or what you’ve been hired for is a pleasure in itself. It keeps you going and is infinitely rewarding. Also, you’re learning something new outside of your comfort zone which keeps things afresh. Curiosity does not kill the cat, it just makes the cat more skilled!
  • The ability to prioritize while multi-tasking: These are skills that I am still juggling and struggling to master, but I hope I’ll be there in a bit. You’ll have a thousand curve balls thrown your way, but pick the ones that matter in the long run and creates maximum impact in the short run. You’ll definitely be more productive.
  • It’s okay to ask questions: I’m a tad bit slow at data crunching and when numbers are thrown around, I take a minute or two to process them. That’s okay, because I have accepted this and I often ask for things to be repeated. Initially, I was shy to ask questions, but I was the only one losing out in the process. I was lost and never on par with the team. It’s okay if you can’t word the question right, put it out there and you’ll find some clarity. It’s definitely better than being absolutely clueless.
  • Your tribe defines your vibe: The opposite of ” Your vibe attracts your tribe” holds true too. There are a few at Headout (not picking names, but you know you) who love the company as much as the ones who founded it, questionably more. And like every organization, there will always be another group of folks who consider this just another”workspace”. I’m not sure how it so happened, but my tribe at work is largely the former group – the ones who so passionately love Headout that every conversation with them was defining, to say the least. You spend half your day with your colleagues, and their opinions and attitude are bound to influence yours. Choose your work-tribe wisely.
  • Data backing & brevity goes a long way: If you have a point to make, always have data and facts backing you – no room for assumptions and speculations. I’ve sat through many meetings and the most effective ones are where numbers do most of the talking and ones that don’t last for more than 25 minutes. We, humans, have a really short attention span, so if you have to put a point forth, it needs to be quick and easy to grasp. Aditya Kulkarni, thank you for making me realize this!
  • You will mess up at some point, but it shall pass: We’re human and we make mistakes, but half the battle is won once you own up to your mistakes, spin that into a learning moment and work on the quickest fix. Try not to mull too long over your mess up and figure out how you can make the best of the soup. I would love to quote a few anecdotes here, but my team will most definitely disown me, so…..

Long story short, two years at Headout has been many rewarding things – a steep learning curve, a humbling experience where I’ve met some of the smartest folks in the industry and enriching, both personally and professionally. Ending this with a quote I came across early on in life and fortunately live by,

” Choose a job you love and you will never have to work a day in your life”.

Casually flaunting my Headout tee with a colleague!

When I started writing this article on March 5th (yes, it’s been in my draft for a month), the world was in a different place. As I complete this article, we’re in the thick of the COVID-19 pandemic – borders are sealed, countries have been on month-long lockdowns, social distancing and quarantine are words thrown around like confetti and India is 10 days strong into a national lockdown.

The travel industry has been severely hit and Headout as an organization has had to revisit and revise its objectives for 2020, a year that started out as a promising one. Even through these rather uncertain times, I am in awe of what we’re doing as a company. Everyone’s picked up new projects as some of their earlier tasks have taken a backseat for now, projects that were shelved are finally being dusted and attended to, and we’re constantly working to keep the travel community inspired and engaged. We’ve even launched a virtual travel project called Headout From Home which I’ve personally worked on, and am so proud.

Until the world settles itself back to normalcy, looking forward to incessant slack pings, mostly-muted hangout meetings and some of my life’s best work!

Disclaimer: This post was originally published on LinkedIn.


Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

This site uses Akismet to reduce spam. Learn how your comment data is processed.