📁 Starting a New Save File
Moving onto your next career stopping ground
As I was between jobs in September 2022 for two weeks, I reflected a lot on my previous job and mentally prepared myself for my current role.
Thus was the birth of this running list of lessons learned.
Put yourself first…
There is nobody else with as much skin in the game that is your life and your career as yourself. Look out for yourself, your dreams, goals, needs, and wants first and foremost.
Keep in mind that you can prioritize yourself while still acting in the best interests as an agent of the company you choose to work for.
…And acknowledge that work is a two-way relationship
Continuing off from the previous point, to me, jobs are similar to relationships in that they should be a two-way street.
I typically try to stay away from making work sound strictly transactional because I think there is room for a lot of soul behind work; however, for the sake of analogy, I’ll put this principle in the backseat for a moment.
As an employee, I’m exchanging my skills, knowledge, and time for compensation, learning, and some sense of purpose beyond my professional responsibilities.
As soon as this “equation” is no longer balanced, that’s when I now know it’s time to revisit my relationship with work.
Life and work are so closely intertwined—it’s important to make the relationship between them symbiotic.
Write a user guide for the work that you do
Documenting different aspects of your job as you go, especially when you're the first of the role in an organization, makes preparing for transitioning in-flight initiatives much more efficient and less stressful on everyone involved if and when the day comes when you decide to move onto a new role.
Two weeks before my last day, I finished documenting as much as I could to artifacts I had owned, such as a product strategy brief, a product positioning brief, a content strategy, a content style guide, a product analytics tool decision write-up, and product requirements documents.
Afterwards, I consolidated links to all these documents in a separate transition document, in which I also called out the status and remaining work to be completed for each artifact.
Process negative emotions as they surface
As I was preparing to give my formal two-week’s notice, I experienced feelings of guilt. I worried about how my manager and skip-level would take this new. I worried about my teammates in Product Development who would have to pick up on some of the work I would be leaving behind. I felt like my leave would be an inconvenience to everyone.
There never is a “best” time to leave a job if you feel ready to move on. It’s a natural course of events in the modern career, especially if you’re working in tech where a lot of folks change jobs every 2-3 years.
Assuming you’ve done your due diligence in handing off or transitioning assignments, how the company redistributes work once you have left says everything about the company’s leadership and nothing about you.
Create and maintain relationships to build out your (support) network
Keep in touch with folks. Offer help where you can. Congratulate them on their big life milestones. Share information that you come across and think they would find valuable.
You never know when the seeds you've planted in sowing and cultivating your relationships over time might bear fruit for your next career opportunity. The universe works in mysterious and sometimes miraculous ways. ✨
Personally, I’m not a fan of seeking out a relationship with someone with the expectation that they will help you in some way, such as offering a referral. As the receiving end of these requests, it feels disingenuous and puts me in the awkward position of having no idea of what someone is like as a person—let alone what they’re like as a professional.
Seek progress over perfection
It's okay not to find the "perfect" job. An objectively perfect job doesn't exist.
Know what criteria you can or will not settle for.
Coincidentally, John Cutler explained the concept of drivers, constraints, and floats that he had read from Johanna Rothman’s book Manage It! in a webinar. I saw an opportunity to use the mental model to assess my career move, —in addition to my usual go-to decision matrix—so I did that for myself.
In particular, I think it’s important to call out setting “exit criteria” for a new job—that is, what are the signals or the things that indicate it might be time for us to consider moving onto our next opportunity. There are frameworks, principles, and other tools that cover job “acceptance criteria”—that is, what the requirements that we must have or would like to have in a new job to take the opportunity—in spades, yet I haven’t read much about so-called exit criteria.
Reframe interviews as conversations
You're getting to know the role, manager, team, and organization.
Try not to put unnecessary pressure on yourself, such as telling yourself,
"I need to succeed to make it to the next round."
Be present in the conversation. Focus on how best you can be of service and why you could be the greatest fit for the role.
Show up as yourself in interviews. There's no better version of a person you can be!
Before my interview panel with Okta, I watched this video to hype myself up.
Care about inputs; check the outcomes
What you have full control over is doing your due diligence.
In an interview setting, this looks like:
Preparing yourself to the best of your ability and availability in terms of preparing your narrative around the skills and knowledge needed to succeed in the role based on the job description and familiarizing yourself with the company based on the company website;
Preparing a few questions that you can’t easily gauge from publicly available information about the role, team, or company;
Paying attention to the conversations you’re having over the course of your interview loop to ask thoughtful ad-hoc questions; and
Making sure you’re taking care of your full self, so you can be fully present.
Beyond this preparation work, everything else is outside your control, such as:
How much the folks interviewing you like you;
Who the other candidates also going through the interview loop for the same position are; and
So much more!
Make self-reflection a habit
You might be oblivious to signs or signals that indicate it might be time for you to seek a new growth opportunity elsewhere.
This is particularly true if you’re not in the habit of “coming up for air,” or checking in with yourself outside of your day-to-day work.
These are some open-ended questions I reflect on at least once every week now:
What did I accomplish? What am I proud of? What did I find challenging? What did I learn? What do I want to focus on accomplishing next week? Anything else?
Saying goodbye is hard—and may only be temporary
Great teammates and managers will be happy to see you grow with your next role, even if they're sad to see you go.
The world is both big and small; you never know when you might cross paths with a former teammate or manager again.
Make sure your needs are being met.
There is a lot of soul involved in our relationship with work.
Write a how-to guide for your job.
Reconcile your negative emotions as you feel them.
Make genuine connections with whom you cross paths.
Aim to be better than you were yesterday—every day.
Challenge your paradigm on interviews.
Learn to detach yourself from the outcomes.
Create time and space for thoughtful, intentional self-reflection.
“Goodbye” doesn’t have to be forever.
Thanks for reading this month’s edition! 🙏
If you have two minutes, I’d love to hear from you and learn about you in the comments:
Which of these lessons learned resonated the most with you?
Based on your lived experiences, what else would you add to this list?