📈 How to Know When to Move On

Hey friend! Welcome to Level Up 📈.

Every Sunday, I dive into one topic to level up your career. This week, I’m focusing on knowing when it’s time to move on.

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Today at a Glance:

• Real Life Example: My Lesson On Moving On

• Deep Dive: It’s Time To Move On

• Reader Q&A: Taking The Leap

Read time: 5 minutes

My Lesson On Moving On

In December 2023, I was in a pretty dark place. My first company wasn’t working out.

While we had happy customers, the market wasn’t big enough to sustain the business. To add to the pressure, my co-founder decided to leave, leaving me with a big decision.

Do I stick with the current product and wait for the market to grow, build something adjacent for the same customers, or do a full reset and start over from square one?

Conventional founder wisdom says “be resilient” and “never give up”. Starting over also felt daunting—I didn’t know what to build next and didn’t feel like an expert in any particular field.

I ran a couple of experiments by building two adjacent products and neither of them took off so I decided to step back to square one.

It was tough—I was burned out, exploring different industries, and honestly felt lost. But after 7-8 months of daily work, I found a problem I felt well positioned to solve: helping people build their LinkedIn brands and businesses. That’s how Saywhat was born and now I’m pretty confident I’m onto something here.

The lesson for me? Fear of the future isn’t a reason to stay where you are.

Deep Dive: Knowing When to Move On

Why can’t you move on from a dead-end job?

After speaking to hundreds of people about this, I’ve realized it all boils down to one thing - fear.

• For people in middle or upper management it’s fear of uncertainty. They've got loads of responsibilities, and the question is always, "What if I fail?"

• For juniors and associates, it’s fear of judgment. They don’t want to leave before giving it a fair shot, or they keep waiting for that “perfect” moment to quit.

But here’s the truth: those who successfully pivot or restart their careers do one thing differently—they get over their fear and make the leap.

What are the signs you need to move on?

1/ You’ve Stopped Growing.

• Feeling stuck when you’re in the same position for too long is completely normal. When learning and growth hit a ceiling, it can be frustrating. 

Here’s What You Can Do: Look for new learning opportunities—ask for stretch assignments, take interesting online courses, or explore mentorship to break the stagnation.

2/ You’re Always Waiting for the 'Right Time'.

• You keep telling yourself, "Just a little longer", and delaying your exit. News flash: there is no right time. Don’t use planning as an avoidance tactic from actually moving on.

Here’s What You Can Do: Set clear goals with deadlines. For example, aim to finish a course in three weeks, update your resume in two weeks, or find a mentor in a month.

3/ Your Gut Tells You It’s Time.

• Whether it's about growth or culture, don’t let fear of failure keep you stuck. If your gut says it’s time to move on, listen!

Here’s What You Can Do: Trust your instincts. Start by updating your resume, expanding your network, building a personal brand, and taking that first step toward a new opportunity.

4/ You’re Undervalued.

• Staying in one role for ages often leads to being overlooked. It’s tough when your hard work is consistently unnoticed.

Here’s What You Can Do: Track your wins and how they impact the company's goals. Focus on data and results. Then, have an honest conversation with your manager.

5/ Your Work Environment Drains Your Energy.

• If the people around you consistently leave you feeling drained or unmotivated, it’s a sign to pay attention. Negativity and drama can affect your mental well-being and productivity.

Here’s What You Can Do: Learn to set boundaries—remember saying ‘No’ is a form of self-care. If it persists, work on your exit plan.

6/ You're Not Challenged.

• Growth comes from challenges and stepping out of your comfort zone. But it’s hard to stretch your abilities if you’re on autopilot every day. 

Here’s What You Can Do: Start by delivering high-quality results in your current position. It’s easier to ask for more responsibilities when you’re a top performer. Don’t just meet expectations; exceed them.

7/ Your Goals Have Changed.

• As you evolve, so do your goals. What you wanted at 30 might not be what you want at 40. It’s time to realign and adjust your path.

Here’s What You Can Do: Take a moment to reassess what you want. Is it a new role, more money, or maybe starting your own business? Align your actions with your new vision.

8/ You’re Dreaming About Other Jobs.

• If you find yourself wishing for new challenges or envious of others in roles you aspire to, it’s a sign you’re ready for a change.

Here’s What You Can Do: Channel that envy into action. Research roles that excite you, network with experts on LinkedIn, and start upskilling to prepare for your dream job.

If you need more inspiration, watch this: Career Change: The Questions You Need to Ask Yourself Now

(P.S. Here’s a post I wrote about this that got over 23,000 likes.)

Reader Q&A: Taking The Leap

Each week, I cover a challenge from a member of the Level Up Community, sharing the problem and how I would approach solving it.

Hey S,

Congrats on taking this big step! Changing careers is tough, and many people struggle with it. Just remember, with any career change, there’s usually a ‘learning’ phase before the ‘earning’ picks up.

Here’s what I’d suggest:

1. Clarify your direction - Reflect on what you’ve enjoyed and where you’ve thrived in past roles. If you need more clarity, consider doing a career assessment like this one.

2. Match your skills to market needs - Map out your top skills and ask: What am I best at, and who would pay for this? Look for opportunities where your skills can shine and add real value.

3. Research industries on the rise - Look for jobs that match your old salary while aligning with your strengths and interests. Stay informed about growing industries. 

4. Build your personal brand - A strong brand can set you apart. Pick a platform (LinkedIn is a great start) to share your story, skills, and interests. This helps you connect with people and opportunities that match your new path. I’ve written more about building your LinkedIn presence here.

5. Use your network - Use your connections to find intros into interesting industries. Cold emails and social media outreach work too. Here’s a more detailed guide on mastering networking.

Bonus: For extra inspiration, check out this video from Jay Shetty - its all about leveling up and finding purpose.

Hope this helps!

Want to be featured? Email me what you’re struggling with!

Good luck leveling up this week.

Talk soon,

Will McTighe

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