December 20, 2024

It’s been almost two years since the involuntary exit from 25+ years of seamless corporate employment left me wandering in the wilderness. It quickly became apparent that my years of experience were a hindrance to a corporate mindset fixed on short-term gains over strategic preparedness.

I needed a new option. It would take me a little over a year to build a freelance professional career.

I wish I had started sooner.

If you’re lucky enough to still have a job as an experienced professional in this economy, take some time and start thinking about what’s next. Here are five questions that I wish I had started thinking about years ago.

Five Questions Every Corporate Professional Should Ask Before 2025

1. "What advice do people keep asking me for?"

The people around you usually know what you are best at. What do people unfailingly come to you for help with?

Be sure to cast the net wide on this question! If you volunteer your time in some capacity, what do people appreciate most about what you bring to the organization? What do friends say you’re great at?

You are far more than your job title. Begin to appreciate that.

2. "What problems do I solve that my job title doesn't reflect?"

Few experienced professionals are lucky enough to spend most of their time in corporate employment doing the things their job description says they do.

What are your shadow roles? What sorts of things do you make happen simply because there’s no one else that will do it (or do it well enough)?

If you’re at all like I was, this will end up being a long list.

3. "What Energizes Me vs. What Drains Me?"

One of the most common mistakes I see while working with corporate expatriates who are choosing to become independent professionals is that they default to what they were most recently doing. They get some distance down the road of building a successful business when suddenly it dawns on them that they never really liked doing that.

Your resume doesn’t matter as an independent. You’re more than the sum of your job titles.

Being a solo professional is a long road. Thinking carefully about what brings you real joy and passion is crucial to a sustainable future.

4. “Where do you see patterns that others miss?"

If you’ve been at a company for a long time, you begin to see patterns all over the place. This is one of the most valuable skills you can leverage as a solo professional.

Think about instances where you were able to see around corners and plan for something no one else had even begun to consider. Think about how you can leverage that to help businesses facing the uncertainties of the next decade.

5. “What seems obvious to you but amazes others?"

Your most valuable skills are often the ones so natural to you that you discount them entirely. Pay attention when people say things like, "I never thought of it that way" or "How did you know to do that?" These moments reveal your superpowers.

Trail Marker: Track your Shadow Consulting

Start a simple note on your phone or in your paper planner. Each time someone asks for your professional advice, note:

• Who asked (role/department/relation to you)
• What problem they needed your advice on
• What advice you gave them
• The outcome it had on their situation

Review this regularly. You're building a map of your natural expertise areas.

View from the Summit: Why December is Perfect for Planning Independence

I love the holiday season. The natural slowdown in corporate environments and most (non-retail) businesses, coupled with our natural instincts to pause and reflect, makes it a perfect time to ideate on the future.

Beyond the five questions I noted above, here are a few more general tips for getting a start on your 2025.

It’s natural to think in terms of goals, but a goal without a system to get there is like planning to summit a mountain without a trail map.

A great resource for this is the book “Atomic Habits” by James Clear. I make it a habit (Ha!) to re-read it every year about this time and build my strategies for 2025 based on his excellent framework.

Don’t self-limit! Anyone who has amassed years of success in a corporate environment has a lot more skill and experience than they realize. Give yourself room to dream.

Talk to friends and trusted colleagues and, if you can, record it. You will get amazing insights into what drives you when you are speaking from the heart. Encourage them to help you dig deep and keep answering “why”.

Above all, take time to relax and recharge. You can’t make progress to your destination if you can’t see clearly.

Ready to Move From Reflection to Action?

If these strategic questions have sparked something in you—a realization that 2024 could be your year to make the leap to independence—I invite you to join our first Freelance Base Camp Cohort + Community, launching January 7th.

Over 8 weeks, you'll join a small group of experienced professionals who, just like you, are ready to chart their course to independence. Together, we'll:

• Transform your corporate expertise into a clear, independent business model
• Build your social messaging strategy
• Create sustainable systems
• Connect with others making the same journey

Most importantly, you won't be climbing alone. You'll be part of a supportive community of Strategic Independents who understand exactly where you are — because they've been there too.

Spots are limited to ensure personalized attention and meaningful community connections. Early bird pricing ends December 25th.

→ Learn more about The Freelance Base Camp Cohort