On Careers…

Jun 1, 2024Insights

I’ve had several people reach out recently to discuss their career paths. Each person was in such a different place, so it stands to reason the advice I had to share looked quite different. It made me think about the different moments in my career, advice I’ve been given, and what sage wisdom is worth sharing with the world. So, let’s take a look at a few scenarios and the considerations impacting each.

There seemed to be a common denominator in each of the situations: a slow grind. This is when you find yourself treading water for too long, not ascending and feeling restless. The fascinating thing about this is that it can happen across so many levels, and it can feel just as frustrating at each. For those early in their careers, it can seem as if you may never break through a middling level of success to a place where your work can stand out and you can feel seen. For those deeper into careers, this situation feels like a glass ceiling preventing you from maximizing your skillset and applying it to a strategic level in the organization.

career advice

Like most situations, how you handle it is highly dependent on the organization. Jill and I spoke with someone recently who was ready for a new challenge. This person had excelled within their current position and made a fantastic brand for themself, but they effectively outworked the position they were in. This is a tough spot to find yourself, and equally tough for an employer. On one hand, an org could create a position which maps to the individual’s skill set, which seems like a fantastic idea on the surface. But what happens when that individual eventually moves on, as people are apt to do? It leaves a void in the org that was so tailored to an individual that it becomes impossible to backfill, necessitating a reorg.

I found myself in a similar position after my first job after college: I had built a mountain of assets that outpaced the company’s sales trajectory, leaving me in an awkward place. Even when the org is a great place to work, if there’s not a clear path forward or your skills are outmatching your position, it can be time to move on. These situations often result in boomerang rehires, so remember not to close the door behind you.

I met another person who returned to work after spending a few years building a family. She was working for an organization that had a peculiar habit of not promoting people with less than 10 years of tenure, regardless of experience or performance. Pair this with the people who were ascending being ill-fitting for their leadership positions and it becomes an extremely frustrating situation. This is an immediate red flag, because any organization that will ignore, or worse, not recognize the capabilities of their people is not prepared to make good decisions for themselves or their people. This creates a terrible situation rife with mentally-challenging “am I good enough” moments. When this person’s boss departed and the org would not even consider her for the position, despite being the perfect match, I advised this person to move on. She is now thriving in a much healthier work environment. 

Another person in a similar situation was feeling unsatisfied with their salary, feeling the slow slog was wasting their prime earning years. This is a very real feeling that I can empathize with. In my 20s I was frustrated by the feeling of putting in what seemed like more effort than my superiors and receiving far less compensation. In my 30s I made some career moves that aligned more with organizations that were structured differently and taking positions that had clearer sight-lines to revenue generation. I think when it comes to compensation concerns it’s important to step back and examine whether your position or the company’s structure is the right fit for your goals.

Consider the ownership structure, because that directs a lot of the financial goals of the org. Venture capital-owned companies are often in a cycle of shaving costs while driving growth, which can feel like a meat-grinder. I worked for a company in which I was being asked to train low-cost labor overseas to do the same work I did in preparation to sell the company. This didn’t sit well, and I ended up walking away from a promotion offer to start a new job elsewhere. In the following year the org I left went through several rounds of layoffs as they continued on their cost-cutting path.

Looking back, I’d say my career is spotted with as many fumbles as there were smart moves, but I really value and appreciate the mentors I had in my life who helped guide me when I felt lost. I love being able to share perspective with others almost as much as I enjoy learning from those who have come before me, and while I am no career guru, my door is always open.


 Justin Sutton


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