They say that during times of major transition the first 90 days are absolute critical moments — the moments that have an impact that can cascade and have long-term effects.
Getting these moments right can be challenging, but they are important to get it right. I happen to subscribe to the belief and have used this to shape the plan for my life.
February 8th marks the date I left my position at Trilogy Education after they acquired the company I co-founded, the Firehose Project.
The flexibility and freedom has been liberating, but also daunting.
On the one hand, I have pure joy from considering an unlimited number of possibilities that could drive the purpose of my life for the upcoming years. Starting a company gave me learning, experiences, and perspective I couldn’t have achieved any other way. The trade-off was that it required my intense energy and focus for every minute. This time off, without a specific job-title, role, or organization that I’m working for has given me the opportunity to shift my focus, and delve into things that excite me and quickly forget about the things that lose my attention.
On the flip side, I feel anxiousness about starting the next phase of my journey. I consider myself an ambitious person and I’m eager to start.
Writing about my personal north star earlier this week helped to give me perspective about the opportunities I’m considering. Most importantly, writing these down gave me a new perspective to consider: why does this seem like a good use of my time.
Next week will close out the 90-day mark of having a defined purpose and been a more ambiguous journey. As this phase is ending, clarity of what my future - or at least a few of the upcoming months - will entail is becoming clearer.
Here’s how I approached the first 90 days.
First, I took some time to decompress. I started working out consistently and went on a number of trips with my girlfriend. A couple of major milestones in my personal life:
- cut back on coffee intake
- began a consistent exercise routing (lifting weights, outdoor running, and bike riding)
- making and drinking juiced vegetables each morning
- travels with my girlfriend, including two trips to Los Angeles, a number of short-trips just out outside San Francisco, and a 3-week long camping road trip that took me to Sequoia National Park, the Mojave Desert, Albuquerque, Chaco New Mexico, Sedona, Santa Fe, and a bunch of stops in between.
I slowly gained perspective about who I am and accepted this next phase of my life.
Second, I started trying to use the time I had to gain clarity about the next steps for my work-self, too.
Here are the steps that I used to find clarity about the next steps for myself professionally.
Step 1 - I asked my advisor for his advice
My advisor had given me help at a variety of steps during my journey. He helped me at every point, from starting it, selling it and also transitioning out of the role. His advice to me was this:
Take the time to explore - you will be back to the insanity soon enough, but it is the times when the mind is uncluttered when the creative juices flow. Talk to lots of people as you explore, and you will find the magic when the time is right.
My mind was fairly cluttered. I had some work to do (work resting, relaxing and enjoying life).
Step 2 — I talked to people who had done it before or been in similar situations.
My experience was unique - but other people had similar experiences in the past of starting, or leading great companies and then moving on.
I scheduled a handful of talks with people who would know the answers and took notes. I used these talks to guide my short-term focus and took notes on them to refer to for longer-term inspiration.
I talked to three people for their perspective. Here are the key takeaways I had from my conversations with them. Although the wisdom, perspective, and direction I gained from each talk is difficult to articulate, these are the points that map directly to how I structured and now reflect on this 90-day period.
Solo-founder of a company that was acquired who later joined an early stage startup as an executive, but not a founder.
He took 3.5 months to travel and 2.5 more months to write, explore, and meet people. With regard to his time in transition he told me:
I started cheating halfway through but was able to keep an open mind. The key realization I had was around how I wanted to structure my next steps and learned from my mistakes.
And he had two key realizations that he shared with me about his journey. He told me:
I decided I wanted to optimize more for path vs. outcome.
He articulated it in this very specific way, but translating it to my own perspective:
My Take-away: It’s very easy to fall into a trap of doing things that aren’t sustainable as a founder. Since the journey lasts a long time - make sure it’s sustainable from the beginning - and since it’s such a long journey, make sure to enjoy the journey along the way, too. I thought it was brilliant advice.
He also suggested:
Decide explicitly if you want to do a lateral move or a horizontal move with regards to the position and the market.
In short, he suggested that founding a new company in a new industry would likely come with a lot of challenges. Continuing in the Edtech space could allow me to leverage existing knowledge of the market as a founder, or if I wanted to explore new markets it could be a good opportunity to do so as an employee.
My Take-away: Don’t switch up the industry you’re working in and do the same thing again and expect different results.
Fortunately, my experience working at Trilogy after the acquisition of Firehose taught me a lot about different ways to operate, think and run a business and the different mindsets that it’s critical to foster.
In short, I realize now, that a lot of the things I was worried about most as a founder at Firehose actually didn’t really matter all that much and many of the things that really mattered weren’t even on my radar.
Former CEO of a venture-backed Startup in my network
One big lesson I learned from this conversation was around doing things that require a lot of persistence. We were talking specifically around raising a round of funding, but the advice transcends a lot of situations that I’ve faced in my career and as a founder.
People aren’t necessarily used to situations where there is a very low probability of something working, but only needing it to work a single time to get past it.
It’s not that common in day-to-day life to do something like that. Going into those situations psychologically prepared is important.
This advice applies to switching careers, selling a company, raising funding, or getting the first few customers for a new startup.
Former instructor and a friend who transitioned from a leadership position at a company to a consulting role, who was searching the next step in his journey at the same time.
His advice to me was similar to the advice he took on his own, just a few months earlier:
“You earned the right to be selective.”
Take time off, explore and do things that don’t map to something that is immediately tangible. You only have time now. When you’re weighing what do to you only need one reason to do something. At this point, the argument that something is a waste of time doesn’t matter, it is a resource you have.
He gave examples like driving ubers for the sake of meeting and talking with people, writing an anonymous blog for restaurant reviews and a few other ideas.
Step 3 — Explore
In the entry I wrote earlier this week about my personal north star, I talked about the opportunities I was actively considering exploring as of writing the article.
These were all example of specific things I was interested in and spending time exploring, thinking about and working on.
When asking myself why I found them interesting, I realized I was optimizing for a few different paths:
Path 1: Land a Job
The safest bet would be to land a job. If I went to this route, I’d like to:
- have it pay well
- do something I love every day
- have a path of career growth that would keep me motivated to work hard, learn and improve every day
Path 2: Write a Book
I’ve done a lot of writing and the idea of writing a book is one I’ve toyed with the idea of.
Path 3: Work off Someone Else’s Vision
There are a lot of people with start-up ideas. I know, now, that the process is taxing and having a co-founder is so important.
Since I don’t know exactly what I want to do, I could be open to joining someone who is further along the process than I am.
Path 4: Work off My Own Vision
I could set out to start a company with an idea that I have. The problem, here, is that I don’t really have a vision, yet.
When Marco and I started Firehose, we started projects with the genesis of a variety of ideas. Many of them ideas that Marco came up with, not me, but a couple of them were my idea. Here’s a list of “businesses” that Marco and I started together, all of which generated $1,000+:
- A weekend-long workshop business for adults
- A weekday night events business for adult
- A weekend afternoon meetup for kids
- A variety of short online courses on coding education for adults
An intensive 15-week online bootcamp
- We doubled down on this, and we extended the bootcamp to 22-weeks and offered a 44-week course, too.
- Short-form modular online courses on emerging technology.
I could set out to start something following a vision I have - and course correct as I go - potentially to an entirely new idea that is spawned from initial inspiration.
Path 5: Choose not to decide
If I choose not to decide, it will likely result in me choosing one of the other options, later, however with less time to adaquately prepare for them.
As I’m wrapping up these first 90 days, choosing a direction to focus is becoming more and more important…
Not choosing any of these options means that I will get the benefits of none of them…
Here’s how I’m working on my plan of deduction for the way to follow the process for the next part of my journey.
If I were to take a job and build a career from there, I would want to spend a full 12 weeks of focused job searching before I accept an offer.
Anything less would be selling myself short.
I’ve recently read The Messy Middle and the author, Scott Belsky is an executive at Adobe, and reading this book makes me realize that I would be willing to climb the ladder to become an executive at certain specific companies.
I might not be ready to be Chief Product Officer at Adobe today, if I set a clear goal and set out on a deliberate path to get the experience required, I could get there in the next 5 years.
Accepting a good job, but not a deliberate one to take me to a premeditated goal is the equivalent of me being a leaf on the wind, going where things take me. I don’t think it would be a wise move for my career.
But, I don’t want to accept a job without pursuing one of the other opportunities, first.
I believe that pursuing my own passion will connect me with who I need to find on the journey.
At this phase, waiting to make a decision on my next steps isn’t going to take me where I need to go. And while I enjoy writing, I don’t think that I’m at a point where I’d be happy to focus on writing a book.
Right now, short-term efforts to improve my career outlook might help me marginally, but would only be hedging a bet that embarking on a new venture from the ground-floor wouldn’t work - a distraction that would ensure that I don’t have the focus needed to achieve anything big.
This means that finding a vision that motivates me and gives me purpose should be the goal of the next part of the journey, rather than looking for motivation from elsewhere. It feels right for me.
I can’t wait for someone else to inspire me - and if I’m going to dedicate the next half-decade or more to my next steps - it’s not something I’m willing to skip.
It’s a solid amount of progress - but I do have a couple things working against me, now.
- I don’t have any specific ideas - but I have started the process of finding one and have criteria for what I’m looking for.
- Nor do I have a team yet - but I also don’t know exactly what skillset future team members would need.
But despite knowing very little - the decision to find a meaningful vision is the first step I need to take. With dedicated focus, deliberate work, and energy, answers will come with time.
In the upcoming weeks I’ll be documenting the process and mindsets I’m using on this journey. I also hope to start posting frequent book reviews, here, too.