You may be considering a promising career transition — either switching roles within the tech industry or breaking into tech for the first time.
The challenge is: if you haven’t ever worked in your target role/industry before, you’re left scratching your head. How do I learn if this role and/or industry is a good fit for me? How do I position myself as a compelling candidate using my experiences so far?
You might even feel a sense of existential dread, fear, or anxiety gnawing at you. You’re standing at the divide where the clearly marked path fades and the unknown dirt trail begins, and your feet are glued to the ground even though in your heart you know you need to take a step forward.
So, how do you take that daring step into the unknown?
I’ve been in your shoes before, making two big leaps in my early career. First, switching from incremental nonprofits to the fast-paced tech industry and then again from marketing to product management. Each time, I felt that fear and imposter syndrome, questioning if I was making the right decision.
Fortunately, by the way of these two transitions (and several more to come), I developed a battle-tested system for getting set up for success in my target role. It’s a lot simpler than you might think.
What I do whenever I want to make a career change nowadays is to run an experiment. A career experiment.
Career experiments are a methodical approach to forming and validating your hypotheses about your career path.
What you do is first form hypotheses like, will I enjoy working in this particular line of work? Will I excel in this type of role? Then validate your hypotheses by going outside, doing skill-building projects, and talking to actual people working in your target role (this is critical!).
By the end of running your career experiment, you’ll have built insider knowledge about your target role, foundational skills, and a strong industry network. In other words, you’ll be ready to hit the ground running in your job search.
In this article, I’ll share the best time to run a career experiment, common mistakes of putting it into practice, types of experiments you can run, and finally, advice on how to run them.
The Best Time to Run a Career Experiment
Once you have established a target role and/or industry, you’re ready to run a career experiment.
Plain and simple.
But what if you still don’t have a target role yet?
Don’t fear — take a look at my career mapping posts for steps on how to use your personal values, strengths, curiosities, and lifestyle needs to identify your target role.
Come back to this post once you have a destination in mind.
Three Common Mistakes
#1 Not experimenting at all
Too many people haphazardly jump into the deep end of their supposed “dream job” without putting in the proper research to set them up for success.
For example, coding bootcamps are all the rage right now for aspiring software developers because they position themselves as a fast-track into prestigious jobs that command high salaries.
However, the graduation data of these bootcamps reveals that employment is no guarantee, setting students up for disappointment. Over 20% of students are still are not employed full-time as a developer after graduating from their bootcamp.
What I recommend doing before committing the next 6 months of your life to a bootcamp is first talk to other software engineers in the industry (bootcamp grads and non-bootcamp grads). You’ll get a more pragmatic sense of what a coding bootcamp is good for (“getting a junior developer position”) and what the job search realistically will look like (“another 3-5 months after the bootcamp ends”).
That information is critical to making a good decision on whether or not signing up for a coding bootcamp makes sense for your goals.
Don’t just jump right into the next thing immediately — take the time to run a career experiment.
#2 Running a heavyweight, expensive experiment (like a 2-year-long grad school that costs ~$250K)
This mistake is way more costly than the first one.
While grad school is a fantastic option for select professional paths (medical, law, professional services), I see too many people defaulting to grad school as the solution when they don’t know what they want to do next.
I’ve met many bright-eyed aspiring grad school students who say, “Oh I’ll go to grad school to explore a bunch of different career paths, then just pick one of these paths.”
What grad schools don’t openly advertise is their hidden time commitments like corporate recruiting. I’ve yet to meet a student who had actually successfully implemented their initial career exploration plan.
If your goal is experimenting with a new career direction, try to run a more lightweight experiment that doesn’t break the bank.
#3 Stopping your experiment at the first sign of success
Don’t talk to only one person in your desired industry and then call your career experiment done. Laziness will kill you in this stage because it’ll restrict your sample size and limit your ability to learn from the wisdom accumulated by practitioners in the field.
Remember that you’re reaching out to people to learn from their mistakes and experiences. There will be a natural tipping point eventually when you hear the same advice over and over again, but 1-2 people are not going to cut it. The sweet spot for me has been 6-8 people.
Get out the door and set up more coffee chats, so you get a diverse set of data points and cover your bases.
Types of Experiments
Talking to the Right People
The first type of experiment is to talk to people who are already working in your target role and/or industry.
You want to speak with at least 6-8 people — even more, if you feel like you’re still unearthing mounds of fresh knowledge in each conversation.
Start by leveraging your existing network to find these potential contacts — friends, friends of friends, family connections, college classmates, and former colleagues.
Then once you tap out your network, use the cold email approach. Most people are too shy to do this, which is very fortunate for us initiative-takers. This strategy is the secret to standing out amongst the crowd.
I’ve personally used the cold email to connect with founders/CEOs, VCs, hiring managers, and anyone I come across who has an intriguing background that I want to get to know more deeply.
Keep in mind that cold emails are a numbers game. Don’t get discouraged if you send out your first few messages and only hear crickets. 20% is considered a solid response rate, so there are bound to be stretches of low-response.
Here’s an example email script, which is based on my personal outreach emails that have gotten 40-50% response rates. Just customize the language to your own situation, and then you’re off to the races.
I’m Joseph, a marketer at PG&E. I came across your work while I was researching the tech product marketing community in San Francisco and noticed you also made the leap from CPG to tech 🙂
Can I get your advice as tech marketer for 15 minutes? I’m very curious how you arrived to your current role, because I share a similar starting point.
Would Friday or Saturday work for you? Happy to schedule whenever is a convenient time for you.
OK now that you’ve set up an informational interview with a few potential mentors and advisors, get ready for your meeting.
You have about 20-30 minutes to do a few things: develop a rapport with the other person, ask insightful questions, and lay the foundation for a future relationship. Don’t forget to take detailed notes.
Here are some good questions to ask during the conversation:
- What was your path to get to doing X?
- What are your favorite and/or least favorite parts of doing X?
- What do you think is needed to be successful in doing X?
- What has been surprising transitioning into doing X?
- If you had to do it all over again, how would you get to doing X?
After the meeting, send a brief thank-you email for their time, referencing a specific topic or two you discussed, and let them know you’ll keep them in the loop on your career discovery process.
Doing a Project
The second type of experiment is to do a project.
If you have no prior experiences with your target role, then projects are a good way to start building skills in this fresh domain. But don’t stop with just building the project. Create a way to showcase the project whether it’s a portfolio website or a prototype you can show in person.
Use these projects as leverage to work on even bigger projects or open more doors in the industry. Especially in tech, many hiring managers love to see thoughtfully produced side-projects because they demonstrate curiosity and drive.
- If you’re trying to get into product marketing, then publish teardowns of your favorite product launches including their positioning, competitive landscape, channels, and strategy.
- If you’re trying to become a UX designer, then write articles, showing your finished work product (like storyboards and wireframes) and detailing how you’d solve a particular customer problem using a design thinking lens.
In both cases, publishing your work publicly gets you two benefits.
One, you can collect feedback from people working in the industry and start quickly refining your skillset.
Two, you can start building your personal brand in the industry and make it much easier for people to discover you based on your actual work.
It takes a little bit of vulnerability to put your work out there, but the rewards are worth it. Like cold emailing, sharing your work in the public sphere helps you stand out amidst the masses.
We covered a lot in this article, but the main takeaway is this:
Career experiments are highly worthwhile to do before you start a career transition. They help you stand out in the crowded talent market, connect with influential decision-making, and build relevant skills.
You’ll also learn an incredible amount about whether or not your target role is right for you and the steps you need to take to get there.
Finally watch out for common mistakes when using career experiments like not running them, running heavyweight experiments, and stopping them early.
By putting in the upfront work to run smart career experiments, you’ll be supercharging the rest of your job search and elevating your chances of success.
What kind of career experiment would you like to run in your life? Comment below with your answers.
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