9 Tips for Times of Transition
Most of my blog posts start as private journaling; then at some point my brain says “other people probably need to hear this too” and the ideas make their way onto this blog. This post is no different - I’m hopeful that what started as an iPhone note to myself designed to set intentions for how to navigate a transition that I currently find myself in might also be useful advice for someone else.
Over the last couple of years, I feel like I’ve become the mayor of Transitionville, USA. I’ve found myself “starting over” a remarkable numbers of times in a span of only three years. Most reading this are probably roughly familiar with my journey, but here is the TL;DR version:
April 2020: Got laid off as part of a 65% workforce reduction at Ritual (dope foodtech company that enables peer-to-peer delivery)
May 2020: Feared that COVID was going to make it impossible to find a job. Applied for and accepted a role doing nearly the same role I did at Ritual at UberEats as fast as humanly possible.
Also May 2020: Job offer at Uber was rescinded just before I was meant to start due to an executive hiring freeze. Time to start again.
Still May 2020: Took the above as a sign from the universe and gave myself space to explore entrepreneurship, ultimately leading me to start my first company, indiFIT, a business management software for fitness creators.
February 2022: After a solid two year attempt, we shut indiFIT down. Insert another identity crisis here.
March 2022: Via an introduction from one of our angel investors, my Co-Founder and I get connected to a family office that was incubating the development of a VR wellness game called Maloka. Intrigued, we stepped in to “adopt” and run the company as late Co-Founders.
June 2023: Challenged by slower than expected VR adoption and engagement + comically insane financial markets, we made the decision to hand Maloka off into the capable hands of another organization.
July 2023: Returned to my first love (foodtech) via an exciting leadership role at OpenTable in a season of innovation for the company that is allowing me to put my “whole self” and spirit of entrepreneurship to work in a different way.
There’s a trend you might notice in the above timeline - there are no breaks. The reason for that is that as much as I have had to navigate transition with frequency, I wouldn’t say that I’ve ever necessarily been good at it. I have a tendency to let fight or flight and self doubt creep in during times of transition, and ultimately to let those feelings of discomfort expedite and/or cloud my decision making. But hindsight is 20/20, and now that I have a data set of four seasons of reinvention in a short period, I’m a lot better at pattern matching and self regulation.
What follows is advice that I’ve written to myself, and by way of also posting this on the internet, to anyone else reading this re: how to navigate unexpected times of transition:
Embrace discomfort - from the outside people see an “exciting time” where “anything is possible.” They tell you to slow down and enjoy yourself and maybe go lay by the pool for a second. The tricky thing about transition is that while you are living through it, it usually doesn’t feel good. It’s hard to relax when you wake up every day out of a normal routine with existential dread and the pressure to make life-altering decisions. Your brain runs wild imaging worse-case scenarios (“I’ll never land another job ever again” or “I don’t even know who I am anymore.” These are extreme examples, but you get it.) It’s normal and okay to freak out a little or experience a loss of identify while in transition. Notice those feelings, but don’t let them drive your decision making or lower your standards.
Allow space for duality - times of transition seem to come accompanied with very black and white thinking for some reason. Everything is “are you going to do X or Y?” I think part of this comes with the territory when you’re participating in job interviews and trying to position yourself as one very specific thing. To make sense of those black and white expectations, your brain will try to trick you into trying to adopt black and white labels. Am I startup or big company person? Am I a marketer or a sales person? Am I a people manager or an IC? In reality, nothing is that black and white. Humans are complex and contain multitudes, which often contradict one another or fluctuate in different situations. Don’t waste brain power trying to answer “X or Y” questions - just be a whole person and embrace all of the duality, contradictions, and unexplainable quirks that make you you. For me, that looks like proudly being someone who can happily found a company, work at a startup, or drive change in a massive organization as well as owning the fact that I am a generalist who refuses to specialize in a single function.
As you search for what’s next, hunt for those who “see” you and don’t waste time convincing those who don’t - I had a very strange phone screen at a company whose name I will omit last week. I was interviewing for a role that I met every requirement for (and then some) in an industry that I have extensive experience in, and I was rejected on a first screen. I felt on the call that my recent experience as an entrepreneur just wasn’t landing or making sense to the recruiter - like it was being perceived as a weird career tangent or something that would disqualify me from fitting in at a bigger company. The very next day, I had another phone screen - same industry, similarly sized company, similar role. The recruiter comprehended all of my experience perfectly and enthusiastically pushed me forward. The natural human response to the first call is to internalize that rejection, potentially creating feelings of inadequacy. In reality I had no grounds to feel inadequate - I was perfectly qualified for the role (as evidenced by my experience the very next day.) I was simply talking to the wrong person. As startup fundraising taught me well, the trick is to spend your energy finding the right people - the ones that see and value what you have to offer. Don’t spend one second of your valuable energy trying to convince the people who don’t - simply keep moving and remember that it’s a number’s game. The more people you talk to, the more likely you are to find the right fit. Instead of grieving rejection, celebrate it as one more “rep” on the scoreboard, increasing the size of your opportunity pool and thereby the probability that you find your perfect next step.
Do lots of stuff - so many great things are seamingly born our of serependity. For example, Max Levchin met Peter Thiel, his first investor and the ultimate CEO of PayPal, because he snuck into a class at Stanford because it was hot and his apartment didn’t have air conditioning. Yes, meetings like this are born out of chance and a little bit of luck, but I believe you can at least willingly shift the odds of something like this occuring in your favor. You do that by simply doing a lot of… well, stuff. Go to events, ask for intros, grab coffees, send network updates, etc. - you never know what will come out of them.
Don’t hide - related to the above, something I’ve experienced each time I find myself in transition is an urge to “hide.” There is a certain amount of shame and embarrassment that naturally comes with losing a job, shutting a company down, etc. There can easily be temptation to do it quietly and not draw too much attention to the matter, but I believe that it’s super important to do the opposite. Transition loudly - shout it from the rooftops and tell everyone. Even if folks in your network don’t have the perfect intro or suggestion to help you find your next step, you’ll be surprised what an outpouring of support you receive nonetheless. Simply knowing that people believe in you and are in your corner does a lot for your mindset.
Ground yourself in clear timelines - your perception of time becomes wildly distorted in times of transition. I can’t fully explain why that happens, but I can assure you that it does. In retrospect you’re like “oh wow, I was only employed for 5 weeks” but because every moment of that 5 weeks your woke up with psychological dread and self-inflicted pressure, it felt like 5 months while it was happening. When you’re feeling vulnerable, time seems to move in dog years. I’ve learned that setting clear goals for transition timelines can help keep you grounded in reality. Goals like “I’d like to have applications in for 20 roles within 2 weeks” or “I’d like to be in late stage interviews for 3 serious opportunities within 6 weeks” can help remind you that you are on track even when the days feel longer than usual.
Practice an abundance mindset - This is a hard one because, as mentioned, there is a natural sense of vulnerability in times of transition. It’s easy to let feelings of scarcity, fear, or self doubt take over. Call me woo woo, but I’m a big believer in manifesting what is next. And if you want to manifest something big and awesome, you have to operate with an assumption of abundance. An abundance mindset sets you up for optimism about the future - it grounds you in a belief that there are plentiful great opportunities around you to take advantage of. Thinking this way will help you approach your transition with positivity and zest, thinking big and believing that anything is possible rather than thinking small and settling.
Practice positive self talk - While an abundance mindset helps you believe that there are plenty of great opportunities out there to chase, positive self talk sets you up to believe that you are worthy of and capable of those opportunities. The silver lining of times of transition is that they can often be the preamble to a major growth spurt or leap forward. But if your goal is really to move forward, the benchmark for what is next can’t be what feels comfortable; it must be the thing that feels slightly out of reach and intimidating. The further you’re reaching for your next opportunity, the harder you’re going to have to work to both believe in yourself and “sell” yourself in order to get it. This is impossible to do if you’re stewing in vulnerability and self doubt. To level up your opportunities, you have to level up your confidence. Give yourself pep talks and surround yourself with your greatest cheerleaders on a daily basis.
Don’t overthink it - the gravity of deciding what to do next can become counter-productive if you let it. Sure, times of transition do come with very real pressure and big, important decisions to make, but it is also possible to reach a point of diminishing returns in how much energy you put into making them. The worst thing you can do is paralyze yourself or impair your own decision making by overthinking it. I like to release the pressure valve a little by reminding myself that there isn’t one right answer - there are an infinite number of good things that are all worthy of doing and exploring in this world. Listen to your gut, pick one, and move forward with confidence and conviction.
Happy transitioning, fam.
