Avoiding Going the Wrong Way

Wrong Way Sign

I recently received an email from someone looking to hire the head attorney for an early-stage company. Normally, I wouldn’t give headhunter emails much thought, but this email came from the experienced CEO of a fast-growing startup that’s backed by an impressive list of investors. I ended up politely declining the job opportunity, but it prompted a thought exercise to help clarify the direction I want to move toward.

As I wrote about previously, there are quite a few reasons why I’d want to stay at my current job for the time being. Among those reasons is that, if I stay on the current trajectory (assuming earnings and spending remain constant), financial independence may be within reach in a couple of years. But, for the right opportunity, I would be open to changing jobs, even if that delays achieiving financial independence.

The things that caught my eye about this particular job opportunity were:

  • Head attorney role: Whoever fills this role will have a direct hand in supporting the growth of the business from an early stage and will be in charge of hiring and building the legal team around them, in addition to providing legal advice. That’s a unique opportunity at any company, and is certainly different than my current role as an individual contributor.
  • Experienced leadership team: The leadership team of the startup is well-seasoned, having had multiple successful exits in recent years. They clearly have a knack for identifying opportunities and executing successfully.
  • Backing by top-tier investors: The list of investors who are backing the startup is a who’s-who of top-tier investment funds and industry executives. Those people are in the business of finding the next big thing and clearly think this company and/or leadership team has potential.
  • Sweet spot in business lifecycle, meaningful equity stake: The company is in the so-called “Goldilocks Zone.” It’s far enough along that it has a real product and paying customers and has enough funding to provide runway, but it’s not so far along that its success is assured. In other words, there’s enough risk to make any potential equity payout meanginful, but not so much risk that I wouldn’t consider it.
  • Inspiring mission: If nothing else, the company is ambitious. If it can achieve its goals, its technology has the potential to improve the lives of every person on the planet. And, that’s not hyperbole. That’s the sort of thing that would get me out of bed each morning.
  • Strong work culture: The company currently has a small team, but it’s a tight-knit one. People enjoy working there and believe in the company’s leadership and mission. As evidenced by the CEO emailing me directly, based on a mutual contact’s suggestion, and based on my additional research online, the company clearly invests in hiring and retaining its people.

However, the more I thought about it, the more I realized that this particular job opportunity would move me away from what I’m looking for right now.

I want less stress at work, not more. I currently have a high degree of autonomy, and this role would mean being responsible not only for my own work, but also dealing with additional layers of responsibility (answering to executive leadership, the board of directors and investors, hiring and managing a team, being responsible for legal matters beyond my immediate areas of expertise, etc.). I realized early in my career that I’m not motivated by pursuing the brass ring of law firm partnership and, to feel satisfied, I don’t need (or even want) to become a general counsel or lead a legal team.

Also, many of the things that seem attractive about this startup and make it seem like it has potential are already things that are true about my current company, if not more so (e.g., the leadership team, top-tier investors, mission, work culture). Then, when I thought about having to interview, needing to prove myself over again, and likely taking a paycut to boot, at least in the short term (it is a startup, after all), the opportunity seemed less and less attractive.

I don’t know what I’ll do next or when, but I know I won’t be taking this oppportunity. Perhaps, at a different time or under different circumstances, I’d be willing to invest the energy necessary to be successful in this kind of demanding role. But, for now, I’m going to continue my pursuit of otium, seeking more freedom, not less.

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