There are many reasons you may be thinking about what's next for you. Maybe you were impacted by layoffs like so many others in the tech space… maybe you're feeling stagnant in your current job… maybe you're just not excited about going to work anymore…

Regardless of the reason, if this is on your mind, you may be asking yourself:

How do I know it's time to make a move?


How do I pick the right opportunity so I don't end up miserable again?

Today's newsletter will explore these questions, and give you a framework to help base your decision. So let's dive in…

There are 3 parts to navigating this next step in your career:

  1. Determining whether it's time for a change

  2. Deciding what the right next step is

  3. Finding that perfect role

So, how do you know it's the right time to make a move?

I often ask my clients 3 questions when they come to me with this:

“Do you love / are you aligned with the company culture?”

If the answer is no, you should be thinking about moving on. Remaining in a toxic culture or feeling unaligned with what you do on a day to day basis are both a recipe for burnout and unhappiness.

If the culture sucks, start looking.

“Do you like working for your boss? Are they invested in you and your development?”

Similar to the first but a little different. How great is your direct manager? This person has a massive impact on your day to day happiness, as well as your career growth. If they are kind and supportive, and are invested in helping you build a great career, it may be worth sticking around.

If, like one of my old bosses, you're continually wondering if they secretly hate you based on the way they treat you and dodge your 1-1s, consider jumping ship and finding someone who will accelerate your growth instead of potentially doing the opposite.

“Do you feel as though you're still growing and developing where you are?”

Even if you're working in a great culture for a great boss, if you're no longer learning and developing, your passion for your job may be waning. If this is the case, I would first look at whether there are opportunities in your current company that you could explore before leaving. Having an awesome boss and a great culture are not things you want to give up too easily…

Some of the wrong reasons I see people leave are:

  • A slightly higher OTE ($5K may not make you much happier if you've swapped a great culture for a poor one)

  • Fear of letting go of your stock options

  • Fear of job hopping

  • Sense of obligation to your current employer

If these are the reasons you're staying… ask yourself the questions I've outlined above and maybe give it another think.

Okay, so let's say you've decided it's time to make a move.

How do you know what the right next step is for your career?

I would typically base this on a few factors:

Career Vision

What is the ultimate vision you hold for your career? Where do you want to end up in 3, 5 or 10 years? Evaluate your next steps in comparison to this vision.

Are they going to get you closer to the vision? Further away?

What energizes you or lights you up?

When I was unhappy as an EVP, one day I made a list of 2 columns: What energizes me? & What sucks my energy?

Under each, I listed every single thing that I did as part of my job. Surprise! The ‘sucks my energy' column had a LOT of items underneath it.

I had gotten into leadership because I loved developing people and helping them reach their potential. I was now spending my days in spreadsheets and legal meetings. It's no surprise I was unhappy. So learn from my mistake and make this list now. Find out what things you love and what things you dread… and look for a job that has a lot in the ‘love' column.

What opportunities leverage your superpowers?

You've probably heard that it's easier to lean into your strengths than it is to develop your weaknesses. There's a lot of truth to this.

I spent years banging my head against the wall trying to succeed at a company that I was probably never going to be a superstar at… the stage of company and what the job entailed simply didn't allow me to use my strengths.

Then I moved to a company where I was really able to showcase my strengths, and I rocked it!

So ask yourself what you're really great at. When do you shine? And then find a role that allows you to do that as often as possible. Work is more fun when you're doing things you're great at.

So with all of that said… how do you find this great new role?

My number #1 tip is always: NETWORK. Meet new people. Stay in touch with old colleagues and former managers. Put the effort into maintaining these meaningful connections.

Why? Well, other than the fact that relationships feel good, you'll be top of mind when an interesting new opportunity comes up.

My first VP role came about because one of my former bosses from years before was advising at a young, hyper-growth company and they were looking for a VP, Sales. One day we were having lunch and I mentioned in passing that I was considering looking at new options. He immediately made the connection and thought I would be perfect for this company. And he was right!

Had I not invested in maintaining that relationship over the years, I would have never learned about my perfect opportunity.

If you don't have a great network already, the good news is that social media (like LinkedIn) now makes is easier than ever to connect with people in similar roles and industries as you are.

Either way, your job is to be authentic and invest the time. Build real connections. Be curious about people and help them out where you can. If you do these things, you'll be amazed at the great people you can meet and what opportunities may result.

Until next time friends… ✌️💜