Challenges and Strategies for Taking Time Off as an Early-Stage Founder
Three unique challenges of taking time off as an early-stage startup founder and my strategies for navigating them.
Welcome to A Founder’s Life for Me! I’m Alek, and based on my experiences building companies, I provide practical recommendations on how to build your company and career.
Taking time off as a founder feels different.
My wife and I are about to embark on a two-week safari in Africa! As the date looms closer, the stress of disconnecting is building. As an early-stage founder, I face different challenges than when I worked at larger companies. You’ll leave this article with:
an understanding of the challenges of taking time off as an early-stage founder
my strategies for mentally disconnecting and work planning before taking time off
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Three unique challenges of vacationing as a founder and my strategies for them
Being a startup founder presents three unique challenges relative to being with a larger company:
(1 of 3) I always want to be much further than I am.
What’s different about this as a founder?
When I worked at larger companies and took time off, I would aspirationally think about the job or promotion I wanted. But, there was always a long-term time horizon for achieving these goals, “You can’t be promoted faster than 18 months” or “Wait and see if a role opens up on that team next February.” I couldn’t do much active thinking to optimize for these outcomes because, mostly, I needed time to pass.
Now, with my startup, time is no longer a limiting factor. If I made all the right moves over the course of an eight-week window, my startup could be doing millions of dollars in revenue. The hard part is knowing what moves to make. Rather than time being the limiting factor, I am. So, when idle, my brain defaults to speculating on the right moves for SolidlyAI.
My strategy: Don’t stop yourself from thinking about work while on vacation.
I used to penalize myself, “Don’t think about work; You’re on vacation!” But, by cutting off the train of thought, I’d never scratch the mental itch. My mind would keep going back to strategizing, and I’d end up in a loop…
“What if I tweaked my Sales pitch by doing — Don’t think about work; You’re on vacation!”
[15 minutes later]
“Or I could change the website to have — Don’t think about work; You’re on vacation!”
[5 minutes later]
“I wonder if I can A/B test the messaging for — Don’t think about work; You’re on vacation!”
…
Now, I’ve stopped penalizing myself for thinking about work. I end up with shorter bursts of focused thought; I resolve the thought and don’t need to think about it again. For me, this looks something like sitting by the pool and sketching or handwriting ideas on my iPad. In fact, the idea for starting “A Founder’s Life for Me” came from a poolside iPad session in Fiji!
(2 of 3) Everything is urgent.
What’s different about this as a founder?
When I worked at larger companies and took time off, the pace was much slower; the product/project wouldn’t dramatically change in two weeks of vacation. In many cases, I was also responsible for a small share of the company’s overall revenue. So, even if things did change for the worse/better when I was gone, it wouldn’t have significantly impacted the company.
Now, with my startup, company-level revenue is meaningfully impacted by single-customer relationships. So, all customer feedback is urgent and important.
My strategy: Prioritize the right work before you go and delegate where necessary.
To effectively disconnect, I plan and execute the right work before and after vacation.
Before I go, I avoid starting workstreams requiring me to be highly responsive (e.g., initiating new sales conversations or pilots). I don’t want to be tethered to my phone, constantly checking email, so I avoid putting myself in a situation where that would be needed. Instead, I prioritize workstreams that require time but are less time-sensitive to respond to. In anticipation of my current vacation, I’m sending a revamped SolidlyAI dashboard to a few design partners to hear their feedback. They will have plenty of time to review before I’m back, and I won’t need to urgently respond to their comments.
For workstreams that do require urgent response while I’m away, I either:
Communicate that I’ll be traveling and when I’ll be back. For open sales conversations and pilots, I communicate in advance that I’ll be traveling so the customer doesn’t feel neglected if they email me and I do not respond.
I will work with friends to fill in on workstreams where I can’t do #1. Even as a solo founder, I have people I can rely on. For example, if SolidlyAI were to break while I was traveling, I would have people (friends, old colleagues) who I could lean on to help resolve issues while I was away.
When I return from vacation, I’ll prioritize the work I put off before traveling; I’ll lean more heavily into starting workstreams where I need to be highly responsive (e.g., initiating new sales conversations or pilots).
Creating a plan that focuses on the right work before and after vacation ultimately helps me disconnect more effectively.
(3 of 3) There are fewer people to rely on to handle the work for you.
What’s different about this as a founder?
When I worked at larger companies and took time off, I always had at least three people I could lean on to pick up the slack on any of my projects.
Now, as a solo founder, I have nobody else to rely on when I shut down; progress comes to a halt.
My strategy: Accept that vacation is needed.
The other two strategies I outlined above also help with this, but my main strategy for this challenge is to accept that vacation is needed. In “Not All-or-Nothing: Balancing Professional Dreams with Reality,” I discuss my strategy for continuing to pursue my professional dream: don’t run out of money or motivation.
Disconnecting and taking a nice vacation with my wife is a way to maintain my motivation. I love what I’m doing, but I still need to take breaks. There are frustrating parts of every job; over time, those can outshine the great parts. Taking time away acts as a reset. When I return, I feel grateful for doing the frustrating parts as payment for the great parts.
Effectively disconnecting as a founder.
Taking time off as an early-stage founder on vacation is a lot more challenging than when I was a full-time employee at larger companies. The three new challenges I’ve experienced are:
I always want to be much further than I am. When I’m idle on vacation, I want to think about how to take my startup further.
Solution: Don’t stop yourself from thinking about work while on vacation. Let yourself think about work in focused bursts, if that’s what you want to do.
Everything is urgent. Even though I’m on vacation, I still want to be responsive to customers.
Solution: Prioritize the right work before you go and delegate where necessary. Before vacation, I avoid initiating new workstreams requiring me to be highly responsive.
There are fewer people to rely on to handle the work for you, and progress for your startup will slow down while you’re away.
Solution: Accept that vacation is needed. Sure, things will slow down. It’s better to go slow and keep going than to go fast and burn out.
Thanks for reading! Questions or ideas for topics? Email me.