Future of Work Reflections from a full-time consulting experiment

Hadassah Damien
3 min readApr 6, 2022


Today I celebrate 3 months of full-time consulting as a principal with my firm Staircase Strategy.

Because this isn’t my first [or only!] business, operational elements like becoming an s-corp and setting up contracts wasn’t the main challenge. The challenge has been to be the best boss to myself that I can be, given the volume of work available and my interest in experimenting with work.

I decided to consult rather than take a new full-time job, because I wanted to experiment with a 4-day work week and to reshape my relationship to work, working, labor, and time [I wrote on this, here]. Turns out, a lot of my clients are contending with these questions as well.

A quick recap: since kicking off in Jan 2022, I’ve:

  • Facilitated and strategized with four organizations, two in an ongoing fashion
  • Coached 36 people on innovation methods and small business strategy
  • Run four financial life design workshops

A theme emerging among the other self-employed small business owners I coach is “How do I deal with pandemic burnout, offer things I can charge enough for so I can work sustainably, and work in line with my values?” Team leaders have shared a variation on this: “everyone is oversubscribed, how do we move the important things forward sustainably for our people?”

Over April, I’ll share a few of the approaches I’ve seen work. But first, why this focus on the experience of work?

At the end of last year I had the pleasure of being on a team synthesizing research on work experiences leaders are having and observing. The Work Now report validated that over 3 in 5 leaders are concerned about employee mental health needs because so many people have been struggling.

Many leaders are looking to generate stronger and better work cultures in response — its own challenge. Donald Sull and Charlie Sull on Brene Brown’s Dare to Lead podcast recently illuminated key aspects of toxic workplace cultures based on Glassdoor reviews of companies with higher than average recent turnover — Great Resignation hotspots. These trends were indicators of workplaces where people lacked a sense of respect and belonging.

In non-white collar workplaces, rough “essential” experiences — and decades of wage stagnation compared to cost of living — are driving another facet of resignations and contention with work norms. Jobs that don’t financially value workers are struggling to keep employees, who are themselves struggling financially.

Returning to my clients’ patterns: working on what matters, given the current conditions, is ever present. Determining the criteria of “what matters” will range from social impact to leaps forward via innovative business re-imaginations.

The need is to prioritize based on ROI and healthy workplace cultures and system/social/environmental impact, in order to create value that hits workers [including micro business owners’] multiple bottom lines: people and profit — in a process that creates respect and belonging and contributes to a better bigger picture.

I struck out consulting so I, too, could create a multi-bottom line experience of value. So I could have joyful workplace moments and self-sustain financially as my family’s breadwinner . I’m finding it exciting to be among others seeking to create better ways to work even as I challenge myself to be the best boss-of-myself I can be, to create a culture in my practice where I respect my time, labor, and need for downtime to be my best.

Here’s to the experiments along the way.



Hadassah Damien

design strategist & facilitator // economics researcher @rffearlessmoney // progressive technologist // performer