#43, 77% of Gen-Z will quit within 12 months... What Startups, Microsoft, and Freelancing has taught me about our 'future' of work

This week in the Human Cloud

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Important Updates

  • 👀 55% of employees will look for a new job in 12 months.

  • 💩 77% of Gen Z and nearly two-thirds of Millennials will look for a new job in 12 months.

  • 🍕 A pizzeria in Alabama offered to “literally hire anyone”.

  • 🙌 Microsoft finds that nearly 70% of employees in China prefer hybrid work.

With these outrageous updates, can we finally admit traditional work arrangements are outdated and broken?

Also hint for next week…we’ll be dissecting Microsoft’s Work Index Report that claims ‘the next great disruption is hybrid work’.

TL;DR: My experience has taught me 6 fundamental shifts in the way we work.

  1. We’re all leaders

  2. Personal accountability is paramount

  3. Decentralization makes us all CEO’s

  4. Merit can replace subjectivity

  5. Deep relationships are ever more important

  6. Leading teams lies in access, NOT ownership

1: We’re all leaders

Let’s face it - the corporate kool-aid of everyone being entrepreneurs and leaders is fake. Not because the company is intentionally lying, but because it doesn’t make sense in a typical org chart.

Instead, the Human Cloud is decentralized (buzz word). This just means value is best created through small working teams or solo-performers rather than large top down organizations.

Which for you - means you have both the opportunity and responsibility to be a leader earlier than before since you can build the value to earn your spot at the table without years of ‘earning your stripes’.

2: Personal accountability is paramount

What’s that cheesy Spiderman line…"With great power comes great responsibility".

The Human Cloud is no different. We all now have great power, but with this leadership power comes responsibility for our own actions. We can’t blame things on other people. Whether a PM or CEO the results are 100% on us as individuals.

Take my time as a PM at Microsoft.

  • I didn’t have to work at Microsoft for 10 years to have a budget and headcount. I could hire freelancers fairly easy and had extreme autonomy in my location and working hours (I worked remote most of the time).

  • BUT I was held to a KPI outcome - hit 10 customers by May 1st.

  • If I hit it…increased responsibility and budget. If I didn’t…

3: Decentralization makes us all CEO’s

#1 and #2 create an environment where we’re all mini CEO’s leading our niche (#1) and being held to outcomes (#2).

There’s still a hierarchy. Usually:

  • Visionary: Creates vision, owns project plan, hires/fires

    *usually there’s a rockstar project manager in between visionary and expert.

  • Expert: Owns the outcomes needed each for project plan. If the SEO expert, owns the SEO results.

  • IC: Does the work. In the above SEO example, this might be the writer writing SEO rich articles.

But rather than thinking like an employee following a checklist, you create the plan and own the results.

For independent business owners (freelancers), the Human Cloud puts the burden of typical small business processes like payroll, taxes, bookkeeping, technology management, insurance, etc.

4: Merit can replace subjectivity

I very intentionally italicized the can, because it’s our collective choice if we want this. Also I define subjectivity as everything ancillary to value creation. Politics. Bias. Proximity. These are subjective factors that aren’t directly correlated with the work you perform.

In a Human Cloud this subjectivity can be mitigated or removed entirely.

Take the way I hire freelancers.

I always start with referrals, but if there’s no referral I follow a nameless/faceless process using a marketplace like Upwork or niche specific marketplace like Parker Dewey.

Instead of reading a resume, we:

  1. Ask three questions, usually in order ‘why you, why us, what’s a creative strategy to this’

  2. Copy/paste the answers into a Google Doc

  3. Shortlist the answers

  4. Start with a small project rather than an interview or full hire

Also, if done well, typical remote workflows (like A-sync) put the power of promotion in the work itself. Across my teams and companies I’ve always used the saying, “code is king”. All this means is that at the end of the day, the person that did the work (wrote the code) deserves the stage. In the Human Cloud this is possible!

5: Deep relationships are ever more important

The Human Cloud creates choice. Choice over what you work on. Where you work. And WHO you work with.

This choice creates intentionality that rewards deep relationships with smaller circles of collaborators.

6: Leading teams lies in access, NOT ownership

As a leader your role is to attract, retain, and inspire the right team to bust ass on the right problem.

Traditionally this was best accomplished through headcount. If you were Google this was great. If you were a small business this was impossible.

But today the Human Cloud rewards accessing the right talent, not owning.


  • Top talent doesn’t want to stay in one place.

  • Top talent doesn’t want to stay with one company.

  • Top talent wants to choose who they work with and prioritizes the work itself.

This doesn’t mean the world will be all freelancers. There’s a great reason for headcount. But increasingly technology is making contract talent the better way to attract, retain, and inspire the right team to bust ass on the right problem.

How do other leaders hire freelancers?