How to Lead When You’re Feeling Lost

By Caprice Perry
Sept. 10, 2020

Our guest blog this week comes from Caprice Perry, a communication strategist who helps entrepreneurs and executives build conscious brands. Read on for an exploration of how to find your grounding during trying times.


Whether you’re an entrepreneur or an executive, leading a business is a challenge from the get go. Yet thanks to your clear mission and resilient spirit, you keep on keepin’ on. It’s part of what you sign up for, and those frequent curveballs keep things exciting.

But there’s a whole different breed of challenge you may face, especially here in the wildly unexpected 2020. You may feel lost on a personal level. Leading when you’re feeling lost personally is... terrifying, humbling, wearisome, excruciating...

Whatever the emotion or sensations you’re experiencing, let’s start here -- there’s no shame in that. You’re not alone. As obvious as that sounds, or as many times as you’ve heard it said, you need to hear it again. Put that baby on repeat -- There’s no shame in feeling lost. You’re not alone. Keep returning to that reminder as you proceed. Then...

Pay attention to what information you’re taking in

Think about all of the information you’re exposed to each day. The conversations, the emails, news articles, youtube videos, social media feeds, ads… How do these affect you? Are you feeding your mind the good stuff -- things that leave you feeling empowered, energized or hopeful? Or is what you’re taking in leaving you frustrated, pessimistic or depleted? Take note of the quantity too. Are you taking in so much info that you end up in overload? That’ll muddle your own sense of direction and grounding.

Especially when you’re feeling lost, you want to be sure that what you’re taking in supports you. And be ruthless in eliminating what’s not. You can spend a few minutes in reflection or literally track a full day. Whichever case, the point is to pay attention to what’s serving you and what’s not. How does it affect you?

That awareness is the starting point, and you can shift your activities and behaviors to better support you. If conversations often get stuck rehashing old problems, can you make celebrating wins a priority? If social media leaves you anxious and unfulfilled, can you spend time with a book that makes you smile instead? These shifts can refresh your mindset and help you get back on track.


Reach for what refreshes you

What practices support your wellbeing? What makes your body feel good or keeps your mental game strong? What brings you joy? To find your footing, you’ve gotta’ make these activities a priority. Yep, block out space in the calendar for them. No apologies.

Let’s let go of any notion of needing to follow the over-the-top morning ritual some big deal entrepreneur subscribes to. What actually appeals to you? Or what new practice do you want to explore? Adding something to the mix that isn’t your norm can break you out of a rut. Here are a few ideas to get things flowing...


Let’s talk frequency too. How often do you want to engage in your activities of choice each week? Can you create a rhythm that suits you? Use your calendar or a tracker to make it happen. And if you’re one who experiences guilt trips trying to take up acts of self care, remember -- by taking care of yourself, you’re strengthening your ability to lead your business and bring positive impact to those around you.


Stay connected with fellow leaders

Leadership can be lonely. But it doesn’t have to be. Who are your select few? Who are fellow leaders that are real with you? The ones that nudge you forward. The ones that are the first to admit when they’re wondering what the heck is going on too. Seek out folks that leave you feeling connected, enlightened or hopeful. Steer clear of any that leave you overwhelmed, insignificant or exhausted.

When feeling lost, share your struggles with these trusted allies. It’s easy to close yourself off and get trapped in your own head, but you’ll release a weight when you let others in. This can take the form of consistent, scheduled check-ins (e.g. monthly via Zoom) or spontaneous casual conversations as needs arise. Either way, ask your comrades to hold space for your processing, not tell you what to do. If you’re at a loss on who to connect with, turn to leadership communities and professional groups to meet others. Having fellow leaders journeying with you is especially important when you’re feeling adrift.

Don’t we already know these things?

Yep! These are far from new revelations. But, the way our minds work and the way our society runs, we need the reminders! Repetition is our friend here. Remember…

  1. There’s no shame in feeling lost.
  2. Pay attention to what information you’re taking in.
  3. Reach for the practices that refresh you.
  4. Stay connected with others.

These pointers can help you find your ground when everything about your business and life is looking hazy. One immediate eureka is unlikely, but gradual, consistent intention will help you find your clarity.


Caprice Perry is a communication strategist who helps entrepreneurs and executives build conscious brands. Relying on her experience in brand strategy, creative direction and leadership coaching, she provides strategic direction and solves communications-related challenges. Head to her website for details on client engagements and complimentary office hours.