💡 Starting Your Job Search? Get The Timing Right With These 3 Frameworks

Hello there 😎 

Today in 5 minutes or less, you’ll learn how to know when it’s time to find a new job.

Plus, the best links and resources on remote work. You'll learn:

• 🏢 How to work remotely — even if your company wants you in the office

• 🪴 44-year-old’s garage side hustle brings in $148,600 a year

• 😠 CEOs ready to make remote workers’ lives miserable

Let’s jump in:

⏩ Quick updates

🚀 My group coaching program on Landing A Remote Job launches this week! Learn more about the program here.

✍️ I talk about burning the boats in my friends and family newsletter. You can read it here.

🆕 How Do You Know When To Find A New Job?

When’s it time to find your next job? 

It’s a high-stakes question. But in my experience, no one talks about it.

This is a problem. 

Because move on too slowly, and you could:

• Stunt your career trajectory

• Miss out on title and money bumps 

• Get caught in layoffs

However, leaving roles too soon could mean: 

• Not working on hard problems long enough

• Not building skills

• Or relationships 

There are three approaches to 𝘄𝗵𝗲𝗻 to start your job search:

1/ Annual job search

2/ Always on job search

3/ Job <> Goals Fit

With a volatile job market, we don’t always get to pick and choose when we leave. But we still want to be intentional. 

First, let’s talk about the tradeoffs of being on the job search when you already have a job. I call this the job search spectrum. 

⚖️ The job search spectrum

Every job search comes with an opportunity cost. 

If you’re not employed while searching, it’s everything else you could be doing while job searching, e.g. starting a business, spending time with your family, pursuing hobbies, etc.

If you’re employed while searching, the cost is: how well you do your current job while you search. 

(This is what we’ll focus on, and ideally when you’re running your search. It's easier to find your next job while you have your current one. Less financial pressure, less urgency, and more confidence in interview = you can run a better process.) 

“How well you do your current job” sits on a spectrum. On one end, you’re splitting your time about 50/50. You’re splitting your energy evenly between your current job and finding a new one. 

The upside: you’re focused on getting that new gig, your search is more efficient, and you’ll probably land your next role sooner. 

The downside: your current work will suffer, and any remaining benefit you get from doing your job (we’ll cover that more below) will end. 

On the other end of the spectrum, you can split your time 80/20. 80% of your energy goes to your current job, and 20% is spent on the job search. 

The upside: your work quality won’t suffer much. You can probably keep this up for a long time. 

The downside: your job search will be less efficient, there are higher switching costs, and you could be one foot out the door for a long time, which is a hard way to build a career. 

Since this is a spectrum, the energy you devote to the job search can sit anywhere between these points. 

But no matter your approach, there’s always an opportunity cost.

📅 1/ Annual job search approach

An old manager once told me I should be running a job search every year. 

This should last about a month, and can mostly be a passive search. Take a few informational interviews and a couple of recruiter screens. 

Why? 

• The job search is a skill, and you don’t want to get rusty. 

• You need to test the market and evaluate how much demand is out there 

Here’s the key to the annual job search: 

Once the passive search ends, commit:

If you’re staying, then you stop looking. Focus 100% on the job. 

If you’re going, then ramp up the search and get out quickly. 

🔛 2/ Always on job search approach

I learned this from Scott Adams’ book, How to Fail at Almost Everything and Still Win Big.

Adams shares the following: 

I like this approach…

If you don’t take it literally.

I do not think the message here is you should be sharpening up that resume and going back out on interviews immediately after signing a new offer. 

My interpretation of this is: always be open to new opportunities. Keep doing the things that got you to the dance, whether that’s: 

• Writing thought leadership

• Adding value to others

• Networking

• Advising

Landing a job is not a good reason to turn off those activities

This is how you always have opportunities waiting for you in the wings, rather than going to hunt when you need a job. 

🧭 3/ Job <> goals fit approach

This is the approach I use the most.

I ask: 

"Boxes" are questions like: 

• Am I learning?

• Do I like the culture?

• How is my quality of life? 

• Is the company growing? 

If the job checks enough “boxes”... if the job still fits my goals (hence the name)...

(I am always talking to old colleagues and cold messaging people who are doing interesting things, though. See approach above!)

Everyone’s boxes can be different. Money, brand, team are other common boxes. 

Once the job <> goals fit no longer exists, that’s when my gut tells me it’s time to move on. 

Conclusion

Whichever approach you use to decide when it’s time to move on is fine, as long as you understand the opportunity costs. 

Some rapid-fire thoughts to close this out: 

• There is no dream job. There is no "perfect" company. No single place that will satisfy your every professional need. Dysfunction is everywhere. Ask yourself: "Is this dysfunction I can live with?"

• This does not give you permission to stay at a company or role you hate. You have two options. Fix the situation. Or create a new situation. Pick one. Life is too short to spend half in shadow. 

• It’s easier to grow your career with remote work than not. A lot fewer fake dentist appointments during interview season 😂 

That’s a wrap. See you next week 👋

🤝 3 ways I can help you with remote work: