Jennifer Lien has built her career across Google, LinkedIn, and Facebook by moving toward uncertainty, not away from it.

‍This provocative question inspires Jennifer Lien and informs her work as a life coach.

Asking yourself the right questions can lead to significant life changes, she says. Jennifer does know a lot about embracing uncertainty and making successful transitions.

Her career has taken her from San Francisco to Singapore, Chicago, Australia, and Taiwan. Jennifer hasworked at some of the world’s top tech companies: Google, LinkedIn, and most recently, Facebook, as Head of Enterprise Marketing for the Asia Pacific region.

For Jennifer, getting comfortable with ambiguity is what allows you to keep moving when you don't have a clear map.

This approach comes from consistently learning new skills and immersing herself in new cultures and new experiences. It also shapes her perspective on transitioning abroad and navigating unfamiliar environments. Recently, Jennifer walked away from the comforts of corporate success to become her own boss and pursue her passion – to help others identify their goals and find ways to achieve them.

After seven years at Facebook, she chose to step outside her comfort zone to do something different. “I didn't want to look back and regret not trying.” After all, “what is there to lose?”

As companies increasingly adopt a hybrid model of remote work, or if remote work takes you as far as working abroad, Jennifer’s advice on making the transition as smooth as possible becomes especially meaningful.

In this special Season 3 kick-off episode of The "First 100 Days", Jennifer sits down with host Trinity Nguyen and shares what she's learned about navigating major professional transitions. And how to make the most of the experience.

Top tips for transitioning abroad to a new country

• Determine what you want out of life and how to align your job/career.
• Understand there will be tradeoffs (taxes, salary, distance from home). Many companies will have limitations in flexibility or forward-thinking policies.
• Talk to people who’ve moved to your intended destination. Get the good, the bad, the ugly. Bottom line: get the truth.
• Re-evaluate your decision every couple of years. Create a timeline.
• Make sure your family is on board.
• Be open-minded and remain humble.
• Connect with locals. It’s the only way you’re going to learn.
• Avoid over-researching at the expense of acting (though relocating with family does require concrete planning upfront).

Top tips for a professional transition

• Ask yourself the right questions to reveal insights, obstacles, and inspire breakthroughs.
• Address the emotional blocks and resistance, so you can move forward with your goals and intentions.
• As a manager, encourage your team to work through problems independently.
• Ask the right questions to get people thinking differently and approaching a solution from a new angle.
• Have courage and confidence.
• Move forward before you feel fully ready—waiting for certainty usually means waiting indefinitely.
• Ask yourself, what’s the worst thing that can happen? It’s usually not so bad.

Finally, when it comes to marketers, Jennifer offers simple and straightforward advice:

“Stay true to your audience. Whether you're running ABM, outbound, or demand gen, don't get distracted by tactics that aren't built for your buyers. Know your audience and stay close to them. The channel is less important than the signal. Reaching the right buyer at the right moment matters more than reaching more people.”

‍The pattern is consistent: sharper questions surface better answers and faster decisions.

Jennifer's through-line: identify what's actually stopping you, name it, then build a plan around it.

Listen to the full interview on The First 100 Days podcast-- "What would you do if you weren't afraid, with Jennifer Lien"