This inspiring story by Sam Claassen to make you learn from mistakes made in the past.
Sam is the current Head of Growth at SafetyWing, a Y Combinator-backed startup building a global social safety net for remote workers. He consults for remote startups on the side and has been to 65 countries while mountain biking, backcountry skiing, and rock climbing. Follow him on Twitter
During my teen years, I started collecting things around the house my parents wanted to get rid of. I would sell them on Craigslist for extra money. Even though I learned guitar at a young age, I joked that I enjoyed buying and selling more than playing.
One might predict, based off of this, that I would go into marketing or sales. Yet I spent my first 2.5 years of college in Mechanical Engineering. Despite being in the top 20% of my class, I switched to international affairs. Then to Mandarin Chinese, and finally advertising. By the time I graduated, I had started 4 different degrees at 3 separate schools.
I’m truly a case study of finding my own way by winging it. I wasn’t ‘passionate’ about my field of study. In fact, I chose Advertising so I could graduate faster.
When people ask me if college in America is worth the cost, I struggle to answer. On one hand, I can’t actually learned all that much in classes. When I compare it to how fast you can self-teach with YouTube and online courses, it’s no comparison. But I did meet a pivotal close friend who acted as a mentor through very difficult times.
My early career mistakes
My first job out of schools as a Digital Marketing Manager at a non-profit. At the time, I had talked myself into believing it was my dream job. I was focusing too much on a relationship, and the job let me stay local. It was in a cool outdoor recreation industry, so I thought I would enjoy it.
The organization was incredible. It still is. But I quickly discovered that I was not meant for the non-profit life. Things moved slow. You had to act delicately. There’s not a lot of innovation. The stress is low… but not in a good way. Mostly, I was not intrinsically motivated enough. I felt young and ambitious, and wanted to take risks.
Perhaps what surprised me the most was how unpleasant my day to day life was. At the end of the day, I was still working 40-50 hours a week sitting in an office. When they moved to a trendy new “open office plan”, my life grew even more miserable. To make it worse, I wasn’t making enough to be living a life free of financial stress.
I came to all of these realizations and Learn from mistakes made as my relationship collapsed. It was easy for me to tell you that I was unhappy, but I was unsure of why exactly. Did I hate my job? My career choice? Where I lived? My ambitions?
I wasn’t sure. So I decided to change all of it and Learn from mistakes
Making (massive) changes
Facing the realization that you aren’t happy with your life while you have a job is a luxury. If you’re heavily motivated, that is. It gives you time to explore what you want next. To calculate your coming actions. Since I wasn’t having much fun at my job, I decided to try some things that did seem fun in my free time.
I decided on making my own fitness app prototype. I had literally zero experience in this. Either in app making, or even design. I had used photoshop a handful of times but that’s it. So I took a stab at it using Adobe XD, the beta of which had just launched.
Eventually I ‘finished’ the app prototype and began trying to look for a developer to partner with. In that process, I discovered a new founder making his own fitness app. I sent him an email with my prototype, and asked if he needed any marketing help. As it turns out he did, and although he couldn’t afford me full time, he offered me more than I was currently making to work 30 hours a week. Remotely.
One of the things I had resented about my previous life was only being able to travel for vacations. Now that I had a remote job, I wasted no time in selling my possessions and moving to Southeast Asia. Following my lifelong interest and passion of traveling led me to the concept of nomading – a lifestyle that would continue to guide me into my current role.
Scaling my career
Despite having several interested investors, the founder of the fitness app kept bootstrapping the app. Even though this meant I always stayed part-time, it had very positive impacts on the development of my growth marketing skills. Not having a budget is not always a curse. It’s remarkable what can be accomplished when it has to be.
Since I was never working full time, I would pick up various marketing consulting jobs. Working with 3 – 4 companies at a time is an incredible way to learn rapidly. With every job, I gained a new skill and an additional perspective – all while traveling the world.
Eventually, I met a company through a startup accelerator in China. I spent nearly a year with them in the alps working on the product and their marketing. When the season ended I worked with some media companies and even another fitness app. I took one hiatus from remote work to work for a cannabis company in Seattle. I swore I would never work in a forced office again.
Doing consulting and contracting work early in your career is a huge plus. You get an immense amount of diverse experience within a wildly short period of time. You learn to run your own show, both dealing with stress and discipline. From a startup perspective, I learned what company cultures I liked and disliked, as well as what kind of a team and product I wanted to be committed to.
Joining SafetyWing as Head of Growth
My strategy for picking up contract work was to look at companies hiring for growth roles, and offering contract work until they made a full-time hire. Could be a few weeks for something small, or several months up to a year. It’s a great time to be a growth marketer. They’re in high demand. This means I came across a lot of open growth roles and learned to be very picky.
Eventually I saw a posting in a Facebook group for SafetyWing. SafetyWing sells insurance for remote workers and nomads, so as a nomad myself I had heard of them before. I knew they were a Y Combinator company, and shared a mission I deeply believed in. It’s quite rare to see a job listing that you read and get a rush of excitement about. When you find these “perfect fit” postings, it’s important to jump fast and quickly.
I sent a Facebook message to the employee who made the posting, and also emailed the founders directly. This is almost always the best way to go when applying for a job. Always email who is in charge of hiring directly. It’s fine to include a CV, but significantly better if you can link to a project or portfolio. That really grabs attention.
Almost immediately I had a phone interview. People tend to worry too much about interviews. If it’s a good fit, it will feel like an interesting conversation. As long as you are yourself during the interview, even if you don’t get the job you can be confident that it just wasn’t a good fit. Be sure to offer ideas and solutions during the conversation. It’s great to follow up afterwards with an extra one or two.
How to find a job yourself
I have quite a simple process for this that works quite well:
Step 1: Setup alerts on all of your favorite job boards and groups. My favorite is Angel.co.
Step 2: Find who is in charge of hiring for the role, and get their direct email using a tool like https://www.voilanorbert.com/.
Step 3: Send an email using the email body as a cover letter. It should be short, engaging and to the point. Include links to your experience. Pitch ideas if you have them already. Connect with their mission and culture.
Step 4: If you don’t hear back after a week, follow up again.
- Message people on Twitter
- Email contacts at your “dream” companies, even if they aren’t hiring
- Offer a ‘trial’ work basis to see if it’s a good fit
- Demonstrate you can do the job my making a mock campaign or project and emailing it to the CEO
I’ll end by reminding anyone reading this that I took a lot of rejections early on in my career. Getting your first job or two really is a numbers game. Understand that you may apply to a different job every day and only hear back from once a week. Be patient, and you’ll be rewarded. Don’t lower your standards. The best career advice I ever got was “there’s no point in applying for a job you’re fully qualified for.”