If you’re part of the Leading Generation in a successful family, you’re likely juggling two massive jobs at once.

Job #1: Running the Enterprise
You’re leading the business, the investments, and/or the family office. You’re the operator, the decision-maker, the one everyone counts on to keep the engine running. 

Job #2: Shaping the Future
You’re also the visionary - responsible for preparing the next generation, clarifying the family’s long-term purpose, and imagining what your family enterprise may need 10, 15, or 20 years from now.

Most in the Leading Generation are doing both of these roles simultaneously… and quietly wondering why it feels so heavy.

It is heavy.

Why These Are Two Different Leadership Muscles

In business, we accept an important duality. Every great CEO knows his/her job is to run today’s operations while keeping the horizon in sharp focus - no CEO can wait until the company is “less busy” to think about the future - we must be integrating, into today’s decisions, a realistic picture of tomorrow’s reality.

But when it comes to the planning we do for our families, this truth can be easy to forget.

We assume we can pour everything into the present and somehow the long-term vision for the family will write itself.

Families, just like companies, require both:

• Operational leadership: making decisions about trusts, governance, investments, tax, and philanthropy today.
  
  
• Visionary leadership: imagining the realities of your family enterprise and the circumstances your children and grandchildren may be experiencing 15 years from now.

Both roles matter. Both roles require time, space, and intention. And both pull on entirely different parts of you. Unfortunately, because the operational leadership role can be so all-consuming, the visionary leadership role can be neglected. 

Why This Moment in Time Makes Vision Even More Essential

You’re not imagining it - The world is in transition. So is your family.

Economies are shifting. Technology is rewriting industries. Wealth is transferring at unprecedented rates. Families are becoming more distributed, more diverse, more global.

And while all of that is happening?

Your own children may be growing up, finding life partners, or having children of their own. Family members in your generation, or the generation above, may be facing the struggles of aging and managing related caregiving needs. Roles are shifting. Assumptions are changing. Questions are surfacing. The family system you lead today will not be the family system you lead tomorrow.

This is what makes family leadership uniquely challenging: You’re planning into a moving target.

And that’s why visionary leadership matters. It’s not about locking in a rigid plan. It’s about having an intentional, but agile direction - one rooted in values, aligned around purpose, and built to support the family you will have, not just the one you have today.

Why It’s So Hard for LeadingGen Families

Visionary leadership is more challenging on the family side because family leadership is personal.

LeadingGen parents often quietly ask themselves:

• What if I choose the wrong direction?
  
  
• What if my kids don’t want the future I envision?
  
  
• What if I’m building an enterprise for a family culture that won’t exist in the same way 15 years from now?
  
  
• How do I lead when the future is more uncertain than ever?

These are real fears. And they can make even the most accomplished business leaders hesitate, stall, or avoid long-range planning altogether.

Why Vision Is a Gift to the Rising Generation

The RisingGen often wants to know:

• What future are we building?
  
• Where do I fit?
  
• What opportunities will exist for my skills and passions?
• What is the intended purpose of our resources?
  
• What does “success” even look like here?

When LeadingGen parents take on their visionary role, even imperfectly, it offers stability, identity, and meaning to the next generation. 

Many family leaders are hesitant to share any conversations about the future with their family members until everything feels buttoned up into a perfect package with a bow on top. The reality is that your vision may not ever feel perfectly buttoned-up, but there is likely some conversation that you can begin having with other adult family members in the next generation - even if the input they offer to you is simply sharing what questions they have, which will clue you in to what areas of vision-casting they are currently seeking clarity on. 

How LeadingGen Parents Can Step Into Their Visionary Role 

Here are some practical steps to make it easy to step into your visionary leader role:

1. Schedule “horizon time” on your calendar. 

Not “when things slow down.” Things won’t slow down. Schedule 90 minutes a quarter to think big-picture. Ask your assistant to have you give her a report so you have some accountability. Even if the report says that you thought about a list of 3 items, or read a couple of chapters of a book, you’ve made progress. 

2. Think in 15-year arcs, not 2-year action plans.

Think big picture. No, EVEN bigger!

Imagine your kids/grandkids 15 years from now. How old will they be? How old will you be - oof - scary! What roles might your kids/grandkids be taking on across your family enterprise…even if, for those who are younger, the role is limited to financial stewardship of allowance. How has your enterprise grown in size or scale? Imagine your family members are thriving in this vision of the future. 

Now come back to the future. What one thing might need to happen today to allow your family members to thrive in this future reality? Plan for direction, not perfection.

3. Get out of the vacuum.

The best vision is born out of collaboration, not the vacuum of your own thinking.  

• If you get stuck, hire a coach to guide your thinking or a futurist to describe some of the realities that the future may hold.
• Join our LeadingGen Cohort program, which offers a guided process and lots of tools and resources to help you make progress on building this vision. And the best part is you’ll have the benefit of your peers - other people in the LeadingGen who are just like you - who can share their perspectives on their lessons learned and challenges along the way.  
• Invest time listening to podcasts or reading books on family enterprise leadership. The ideas shared by others who have gone before you can be useful to consider. Reach out to us for our current list of recommended resources. 

A Final Word of Encouragement

If it feels complex, that doesn’t mean you’re doing it wrong. It means you’re doing it well.

Leading a family enterprise and planning for its future is one of the most complex leadership tasks anyone can hold. But it is also one of the most meaningful.

“With great power comes great responsibility.”  Voltaire…and Spiderman

You don’t have to wait until everything is perfectly aligned to start shaping the future.

You just have to start.

We’re here for you - and you’ve got this!