"Treat Sunday night like a career dashboard, check your pulse at 8 PM" - Sunday Scaries as Diagnostics

Reflection on Sunday Night KPI advice from Greg Isenberg that has broad applicability to our ventures, communities, and personal lives.

May 19, 2025

It’s Sunday, and this week has been full of hard work, lots of writing, conducting interviews for a new JOPRO project, meeting friends and supporting colleagues, and having the big questions about “Where Are We Going?”

Many hours this week have been spent on the macro planning of where is the world in 2025, and what can we actually feel good about doing, contributing to, and building ahead. What’s more, I am fresh off of a conversation where I had a tough love moment of deliberation with a good friend whether or not they are invested in their current vocation/industry as either:

they feel they should be, themselves, to do well; or,
they need to be, in order to make the requisite changes to greater viability and sustainable success.

Then I see this from Greg Isenberg:

Check your pulse

He writes:

treat sunday night like a career dashboard, check your pulse at 8 PM:

A) if your stomach knots because tomorrow means meetings you would pay to skip, you need an escape plan

B) if you feel a quiet buzz like the night before a field trip because Monday means fresh momentum, you are exactly where you belong.

that "dread versus electricity" gap is probably the most honest KPI in work

How apt, how fitting, and also, how challenging, especially right now. I would go on to say that not only is it a great diagnostic moment, but its worth reflecting the broader inertia (or sense of direction) at play:

It's a remarkably challenging time to build durable visions and beliefs about where to go and what to do that is of substance in the world today.

Trust, buy-in, vision and relation to momentum

There is a kind of macro-, maybe even meta-leadership that goes on here. Are you conducting your affairs and business in a way that lends trust to others? Or maybe not so much?

We are in a world full of horror stories such as Kevin Xue recently sharing a difficult turn of events regarding PayPal backing out last second on a job offer, after relocating and quitting his old job.

So when we do our ~~Sunday Scaries~~ Sunday Evening KPI check in, it seems critical to make some sober inquiries and evaluations:

What are you feeling right now?
What is the current ceiling (or capacity) of the situation you are in?
1. How is it affected by the momentum level you currently are maintaining, and
2. How easily can that momentum level change?
What is the delta (or relative distance/difficulty) to aligning a good to high momentum state with a vision of the future that is both sober and exciting?

Easier said than done, in some ways, but if you earnestly show up to these questions - and use the 8 PM check in that Isenberg notes above as a starting point, you may begin to discern some answers, or action steps towards finding answers.

Are you in a community that doesn’t regularly support your vision, you sharing your situation, or effective co-regulation? Is the town you are in not fit with the resources your vocation or your desired career path (or changing paths) would benefit from? Is the vision you have for your product or company actually fitting a real market, or the markets that are emerging over the next five years? This can feel like opening a very unpleasant can of worms, especially on a Sunday night.

Community & resilience

Letting the check in be tied to investigating these kinds of questions can serve you well; even if it brings up scary and unpleasant things that maybe you would do better to think about after some sleep and in the light of the week ahead.

Ideally, you have some trusted folks to talk it over with, too.

The key here, though, is to not dismiss the Sunday Scaries and what their diagnostics reveal as merely a typical Sunday night phenomenon.

Rather, give space to think about them during the week ahead, especially if you are finding bigger, challenging problems looming in the distance. Herein also lies one of our super-powers as human beings, and something I think will be critical to be intentional about going forward: helping others to sort these challenges out, as well.

Having community and support around finding those answers and those things to do is vital. Try to help others find their best spaces to be in, and investing in the means to understand what limits folks and allows them to flourish can have huge multipliers down the road.

For the people closest to you, for personal or business ventures, investing in their capacity to manage these spaces, and holding space for their challenges, can go a long way. It may even be a major factor in whether ventures, projects, communities, or relations fall apart, in general.

In primates, grooming isn’t just hygiene—it’s relational. A visual reminder that support, trust, and co-regulation are often built in small, consistent acts of care.

Conclusion and Why It Matters

To recap,

Sunday Check in, what’s the raw feeling?
Seek context for both the Relative momentum & inertia, and Absolute momentum & inertia of the situation you are in
Make note to investigate in the week ahead; give the feelings legitimacy
Seek and support community:
1. showing up for others this way can have many unforeseen benefits;
2. realizing when others cannot show up for you this way has its own insights, as well.

Alignment is a word we hear thrown around in many different contexts these days. In this context, what I am offering some conversation about is aligning your own self with a path towards the future, and seeing how making that a valued part of your own culture and communities can be a centering, co-regulating, and ultimately beneficial practice.

We receive an abundance of advice on dismissing feelings, and I would say an even greater pressuring against having serious and meaningful conversations about the future. For folks that are attempting to build things in the world, this is indeed an almost sacred space, whether or not it is treated with due diligence and reverence.

Granted, my advice indicates a somewhat ideal pathway or manner of resolving conflict - but I mention it briefly here as a reference point; if these things are not tenable, why not? I specifically mention the interplay of momentum and inertia and their relative impacts on the context of the situation you are in, as well as the value of positive and supportive community capable of discernment and resilience.

These things require cultivation and tending to, but they are worthy investments.

Finally, I have long since realized that I (personally) need to keep the momentum moving forward, otherwise I get bogged down in The Horrors of the world. All of this contributes to the ability to do that, and I invite you to consider the role you play in maintaining the the ability for others to traverse meaningful pathways, and reach meaningful destinations.

Both for yourself personally (and professionally), as well as for those close to you and the teams you are leading or contributing to, there is a healthy sense of agency and related skillsets that continue to be essential for surviving and thriving in our world.

Jes Parent on Substack

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