You’ve been in a job for 2+ years. Should you move on?

The answer depends on what you’ve “checked off."

👋Hi, it’s Greg and Taylor. Thanks to everyone who filled out our survey. If you’d still like to take it, here’s the link.

I have a lot of anxiety about my resume. 

I have a great title for my age, but I’ve only worked at two companies (L2 and Section), and neither of them are household names. I haven’t interviewed for a job in 10 years since I followed Scott from L2 to Section. And I haven’t planned out every career move with intention – instead, I’ve taken opportunities as they’ve emerged.

When I talk to my friends, this anxiety isn’t unusual. Whether they’ve been at the same recognizable company (Google) for 10 years or moved around every 18 months, everyone seems to be stressed about what their resume says about them. And this inevitably leads to the question: “Is it time to move on?”

In reflecting on this, Greg and I came up with a career checklist – a list of things you’d ideally have done (and therefore could signal to the market) by the time you’re 40. 

You probably won’t accomplish all of them. But if you’re unsure about whether it’s time to move on, use this checklist to evaluate your current gig. Is your current job helping you check at least one of these off the list? If so, don’t second guess it, and revisit the list next year. If not, it’s time to move on.

– Taylor

The Career by 40 Checklist 

The ideal resume/career is highly personal, and varies by your preferred industry, company stage, and size. If you want to work at a large tech company, more recognizable logos help. If you want to work for a startup, you’ll need to show you can lead through growth and crisis.

We wrote this list to be size/industry/stage agnostic – meaning that if you achieved everything on this list, you’d be a strong candidate for a company of any size/industry/stage. With that in mind, here’s the list.

1. You’ve been at one company for at least four years. If you’ve hopped from job to job for one- or two-year stints, it’s time to get a longer stint on your resume. Moving jobs gets you a bigger salary bump, but longer stints prove that you can stick out “the painful middle” and build something of value.

2. … But you’ve also worked at more than one organization. There’s nothing wrong with staying at a company for 10+ years if it’s checking off items on this list. But a lot of people get stuck in jobs because they’re afraid to leave. Unless your company is REALLY dynamic, you need to demonstrate you can handle different ways of working – and that means different companies. 

3. You’ve been promoted twice at the same company. As hiring managers, we want to see multiple promotions in the same organization, not just lots of separate jobs. Leaving with the same title you were hired with over and over again suggests there was a problem – either you didn’t perform well, people didn’t trust you, or you weren’t willing to stretch yourself. If you’re in a job where you can’t get promoted, look for a job where you can.  

4. You’ve worked for a well-known brand. Like it or not, a good logo signals your value faster than a list of accomplishments at an unknown company. You want to work for a brand that is known as a successful company and known for the way it works (high standards for performance, quality of decision-making, etc.). Think DoorDash over Seamless and Meta over Snap. 

5. You’ve managed a team. And you’ve done all the messy stuff that comes with it – hired, fired, coached (or canned) a low performer, delivered bad news, managed a budget. At Section, Taylor’s hired over 20 people directly and had to manage three layoffs. Some people don’t want this type of management responsibility (and the stress that comes with it), but you should do it at least once to prove that you can.

6. You’ve honed your craft. Last week, we talked about being able to produce a high-quality deliverable as a consultant. But this is equally important for internal roles. You should have 2-3 outputs that you’ve created over and over again across different roles or organizations, and be able to speak to both your output and process. If you haven’t figured out your deliverable yet, you likely need to spend more time in your current or next role – this comes from developing expertise in your function.

7. You’ve been on the hook for something that really matters. This could mean being responsible for revenue, leading a high-visibility project, or managing the most important team to the business. You’ll know you’re doing it because a) it’s very stressful and b) you’re reminded all the time that your boss really cares about the outcome of your work. Section and L2 aren’t strong logos, but they’ve given Taylor experience managing things with high stakes (multi-million dollar revenue targets, c-level clients, etc.).

8. You’ve led through some kind of growth. This is a no-brainer for a resume or job interview – every future employer wants to hear that you grew revenue 100% quarter over quarter. But leading through growth is also an important skill to build. When companies are growing and investing, they want leaders who can put money to work and push their teams to achieve ambitious goals.

9. You’ve led through some kind of crisis. On the flip side, companies also want to see that you can be trusted in a crisis. Layoffs, revenue decline, lack of product-market fit, product recall, etc. All of it sucks to manage through, but it’s essential to building resilience and figuring out what kind of leader you are in tough times. Don’t take a job at a total shitshow of a company in order to do this, but if you’ve never been in this position, consider a role at an earlier stage or turnaround company, where you’re more likely to get this experience.

10. You’ve had 2 bosses who would rehire you. Ask yourself right now – do you have two former bosses who, if you called them today, would find a piece of business for you to work on (or at least connect you with five legitimate job leads)? If not, you need to keep looking for those people. You should have at least two, if not more, by your late 30s. (And if you’ve never had one, take a hard look at yourself – it might be you, not them). 

How to personalize the career checklist

Like we said, career paths are different and personal. Some of these milestones are more important if you want to be a startup executive – others are mission-critical if you want to lead a large organization.

Here’s our assessment of where you should focus based on the outcome you’re optimizing for. 

Our advice

Most career moves are some mix of luck (good and bad), connections, previous experience, timing, and your own ambition or discontent. That’s normal. But we think you can be a little more intentional, especially in the second decade of your career, when you can be more selective about what you work on and where you work.

We’ve seen a lot of people quit our companies to take a new role at another company – but when we talk to them, we realize they’ve done no real due diligence on how it will build their experience. 

Many people do more due diligence buying a new car than choosing their next role. Don’t be one of those people. Pick your next gig with intention, and start to check off this list. So when you are 40, you will be prepared to tackle bigger challenges/opportunities at cool organizations – and get well paid for doing it.

To the next 10 years,

Greg and Taylor