2024: The Year of Opting Out

A societal norm I've unsubscribed from

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Hi, I’m Meg and this is my little corner of the internet where I share tales and observations across the tech and parenting “industries,” with the Goliaths of consumerism and individualism dominating my cultural zeitgeist.

I advise and consult with startups as a fractional product marketing leader, primarily for B2B SaaS companies. Message me with feedback, stories you want me to tell, or a good knock-knock joke (I’ve got a kindergartener) at strategicpivotery@gmail.com

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Going from “all in” to “opt out”

The first time a visitor lands on my Substack homepage, they see this intro:

Today I’m expanding on why I’m opting out of tech bro culture as best I can. And yes, I got that awesome free headshot at a We Gather conference.

In my introductory “why I’m finally writing again” post, I mentioned my conversion to fractional work, aka consulting / contracting / freelancing / part-timing. I’m using “conversion” deliberately: once I started fractional consulting work about 5 years ago, my perspectives on work, ambition, and adding value shifted.

I’ve always been that intense, “give it 110%” type person. I applied this productive anxiety early on and it netted positive results: succeeding as a competitive student-athlete, gaining an Ivy League education, working feverishly at every job I had in city government and then high-growth startups, while also finding time to be a thoughtful and loving family member, friend, mentor, and partner.

My type-A, self-motivated, high-achiever personality found its true home in the hustle and cult-vibes of startupland. It was easy for me to drink and then distribute the kool-aid that these “innovative disruptor” companies served us, alongside the smoke and mirrors of unlimited paid time off and generous expense accounts. I was often deemed a “culture carrier” by executives, but it wasn’t until I became a parent that I was able to clearly identify this strain of culture as toxic to the majority of us.

Five years ago, I was laid off by a (now defunct) media company while on parental leave. Not only was I on maternity leave, but I was simultaneously on medical leave due to birthing another human.

My first reaction to the layoff was righteous anger - as anyone being dumped can be because they didn’t break up with the other party first. Yet quickly, I was relieved. I had been dreading going back to work - not because I didn’t want to find my mind after months of breastfeeding and sleepless nights, but because I was tired of working under false pretenses at this company, and many others before it. While pregnant, I entered the navel-gazing stage of wondering what my future kid would think of what I did for a living. I wasn’t sure he’d be as impressed as my peers were.

I knew for years that there was a power imbalance between companies and their employees, but I didn't do a good job of incorporating this reality into how I viewed work and the rising endemic of workism. In my experience, executives convince employees that their work is not transactional, but transcendent. If employees believe their work is critical to the company’s strategy, they will give more, and be lauded for it. When they are laid off or marginalized or their project suffers from a “strategic pivot,” it’s a shock to realize they are dispensable. Every skipped family dinner, missed workout, or deferred vacation is keenly regretted.

A recent report¹ showed there is a clear “purpose gap” between upper management (tech bros) and everyone else who is working for them: 85% of frontline managers and employees are unsure or disagree that they can live their purpose in their day-to-day work. I’m not sure when working for a tech company (or any company!) became the main conduit for someone’s purpose or identity, but it’s a concerning trend I’m very familiar with.

The best layoff of my life

Fifteen years ago, one of my first layoffs rocked my self worth and challenged my unhealthy workaholic identity. I was miserably adrift without the security blanket of the company’s culture surrounding my life, deeply ashamed I was one of the losers who hadn’t survived the brutal layoffs in New York City. I was a Harvard grad who had worked with name brands like Michael Bloomberg and Goldman Sachs (gross), but it took me over a year to find another full-time job in the middle of the 2009 economic meltdown. My ego was one of the many things to crash that year.

I became a gig worker before it was a fashionable lifestyle choice. I took on any jobs I could get. I temped at a market research firm, but the most consistent gig I had was cleaning an octogenarian’s apartment. The man was the father of a neighbor friend of mine, and struggled with dementia and hoarding. It took two days to clean his kitchen floor, and the next week I came back to find it covered in food and newspapers from the 1980s. This Sisyphean task didn’t disturb me as much as I thought it would; constant clutter meant job security.

The job I got after that layoff was life-changing: I led the launch of the New York City Board of Education’s first ever learning management platform, enabling thousands of kids to access online classes. Ten years later, the platform was used by nearly a million kids during the pandemic.

Yet even during that job and all the ones I had until my “conversion” to fractional work, I struggled with investing too much of myself in companies where practically speaking, our relationship was transactional. If you keep dating f boys, you can’t expect to find a long-term partner (just ask AD about that whole Clay thing).

Embracing the transactional

When I started interviewing for full-time work post maternity leave/layoff, I couldn’t find a position I felt passionate about. I got to the final stages of what would have been an exciting opportunity to me just a few years before. Through the process I had connected with my potential boss Paul. He shared an observation that floored me: “Meg, you are completely qualified for this job. But it doesn’t seem like you really want it.”

I almost burst into tears. Since I couldn’t fool Paul’s high EQ, I opened up and told him I didn’t want to go back to full-time work. It wasn’t until the words were out of my mouth that I realized it had nothing to do with this specific job (which I almost took just so I could work with Paul). I was worried about throwing myself back into the one-way street of startups, where companies insisted I be “all in” all the time, but I was completely disposable to them. I didn’t want to earn another MVP award from a company so mired in a “growth at all costs” mentality that no one took advantage of the unlimited paid leave policy. Some (lucky) people are good at separating work and life, but I clearly wasn’t.

What I needed was a buffer.

For me, this took the form of fractional work. The construct of consulting is a clear, transactional, two-way street. Both parties are transparent about what they want and how they deliver on it. I used to find conversations about money “icky” until it was my job to productize, package, and price myself. I don’t like pricing projects by an hourly rate, but it was an enlightening exercise for me to calculate the value of an hour of my time. Now, every networking call I have is an investment in myself.

Since that conversation, Paul and I grab lunch and conduct a “quarterly personal review” with each other, swapping life updates and chatting about our own, thriving consulting businesses.

Ok, I’m intrigued. But really, how do I opt out?

So many former colleagues and friends have asked to “pick my brain” on how they can become a consultant that I joined Intro so I can help coach people on making the jump. The next, “sister” post to this one will go into more depth into the how, but first I want to recognize a few constraints to this model:

1. Market factors: given the hellish state of the job market, I’d never encourage anyone to turn down full-time work if they need it. It may seem counterintuitive to encourage folks to become fractional, but in my experience a down market can be a smart time to shift to contracting, as skittish startups can’t commit to hiring a full-time employee but may assign budget to contractors

2. Healthcare: not everyone can afford to work for themselves. If you live within the broken healthcare system of America, you may need a full-time job to have affordable healthcare (single-payer system, anyone?). I’m married to a public school teacher, and for years I clocked the slightly-raised eyebrows of my tech bro peers who assumed marrying a public servant would tank my chances of owning a Tesla. And yet I’m fortunate to be married to him, because he has excellent healthcare and neither of us has any interest in owning anything related to Elon Musk

3. Seniority: it can seem hard to find fractional work if you’re early in your career. I think you can, but you have to nail your ideal customer profile and internal positioning

4. Tech bro TAM: one response I get is “just don’t work for a tech bro.” LOL, OK. In the US, startups founded exclusively by women raised 2% of the total capital invested in VC-backed startups.² Working for startups is inevitable in my field, so I focus on advising female and BIPOC founders as a passionate side hustle

Baby steps…here are some ways you can start the opt-out process:

• Identify when you’re burnt out and ask for the things that may help with this: going to part-time hours, taking a sabbatical, shifting job scope

  • Example: when a very good friend of mine became a mom, she told her corporate law firm that she wanted off the partner track and reduced her hours to 75% — they said yes

• When speaking to companies about full-time roles, ask them if they’d entertain part-time work instead

  • Example: a former colleague and friend of mine recently asked a startup if she could start as a contractor first; this allowed her to pursue other options while seeing any red flags at the company before she commits to them

• If your company doesn’t respect your work/life boundaries, be more overt about communicating them

  • Example: peers I know have blocked off time on their calendar with clear messaging such as “School drop off, do not schedule over” or “exercise time”

• Accept that you may need to work at certain companies to make a living, but find ways to ensure you live your values in other aspects of your life

  • Example: I primarily get paid to consult with B2B startups that are Series A or above, but that work subsidizes my informal advising of smaller stage mission-driven startups such as Story Squad and Sunny Period

In my next post, I’ll apply my PMM lens and do a deep-dive on the costs and benefits of fractional work. But truly, the key to opting out for me was that shift in mentality regarding how I want to be transactional. And marrying a public school teacher, of course.

  

1. It pains me to link to McKinsey, but here’s the report. I suggest you watch this instead (start at 22 min for the juice)

2. Per the World Economic Forum report for 2023.