One of the top requests I get is helping to paint a picture of where my clients want to go and how to get there. As we unpack it together — there’s a common set of hurdles that are often uncovered.

December is a great time to make some decisions. Answering these five questions can up your annual planning game, get you through these common roadblocks, and take your business to the next level.

Decision One: Best Time

It’s never the right time

Not all timing is created equal for all people, companies and industries. For some, January is the perfect time to plan – it’s a new year, a fresh start, perhaps just after the end of season rush. You can take stock and head into the new year when business is slower and you have more time to focus.

For others, the year end holidays or summer may afford an opportunity to slow down. This can be a great time to do some reflection, introspection and deep work.

Find your time. Of year, of month, of week, of day. Ask yourself – when are you…

• …naturally curious about the past, optimistic for the future, and realistic about the risks?
• …the least mired in the day to day?
• … willing to step away for a half day (or) 1-2 blocks of 2 hour time to think and create?
• …can follow it up with deep work within the month so you can gain early momentum?

For instance: My month is October. My time of week is Sunday or Monday. My time of month is early month because I’m already fresh from looking at business results and have a better idea where I need to focus. My time of day is evening.

Why October? Two main reasons. It’s my birth month so there’s a natural reflective cycle that happens and I free up over the holidays, giving me time to do deep work and start executing on my visions. For an entrepreneur, the story-line of self and work are deeply intertwined so both of these things matter.

For instance, I recently launched my first product for one of my businesses (The Taste Experience) which specializes in in-home wine tasting playbooks, experience design and facilitation. This playbook was brought to life over the holidays. Prioritizing it in my Top 5 during planning this fall helped make it happen.

Decision Two: Natural Lens

I can’t figure out how to put it to paper

Sometimes people know where they are headed generally but struggle to articulate it, refine it, and put form to it that’s both realistic and will realize meaningful results.

While we are all human with human brains and a human condition, we all tick a little differently. We learn differently, process and create differently, and have some fears that are more pronounced.

Find Your Lens. A lens that taps into your inner best self helps you translate from idea to reality.

Here’s what I mean by that. When you create clarity for yourself, do you:

• …draw pictures or create vision boards or collages representing your goals?
• …write bullets?
• …create spreadsheets?
• …develop mind maps that relate things together?
• …write stories?
• …talk it out?
• …show and tell?

Each of these lenses is aligned to a way of creating and thinking. People think in words, pictures, feelings, conversations and in varying levels of organization and detail. For instance, I create through images, organize by relating information into logical clusters, and mobilize through data, bullets and stories.

To tap into my most creative self – I need to draw first. Each focus area I have a picture for. The measures might change – but the spirit of what I want to accomplish is far less likely to shift. When I draw first, I unlock my potential and get unstuck. Then I can do the heavy mental processing after.

Decision Three: Top Priorities

There’s not enough time and money to do it all

This is a variation on our first theme, but subtly different. In the first decision we focused on not being able to carve out time at all. In this one, we focus on carving out time for the right things. You need to tackle both to move forward.

Have you ever heard the quote: “If everything’s a priority nothing is a priority.” Enough said.

Doing it is the harder part. Invariably we end up with a list of 10 things and it keeps growing the more we think about it.

Ruthlessly prioritize.

Whether or not the old adage Miller identified in 1956 is true (our brains can only hold 7+/-2 things active). Our time is limited and we know from research on agile the effects of context switching in terms of productivity loss.

Prioritization should be kept simple:

• Focus on the few – no more than 5 focus areas (ideally less)
• Be inspired – is it compelling enough to get you up in the morning and impact your purpose
• Drive results – move the needle on your work and life
• Be pragmatic – doable and worth the work. The downsides are clear and you accept them
• Representative of where you spend your time – plans fail when they are extracurricular

When I was building teams to deliver on large programs, the most important and difficult thing was to effectively mobilize teams around common priorities and eliminating static or noise that distracted from progress.

To act on priorities effectively, people need to choose to work on what’s most important right now – not what’s easiest right now. That takes a ton of self management since our brains gravitate towards what we know.

Conversely, people also need to know how to weigh their current energy and channel it when it makes sense and there are alternative options.

Here’s an example. If someone is more naturally adept at knocking out the #2 priority and they are driving around the track at 100MPH, do you slow them down to pull them to priority #1, do you get someone else (or another firm) on it, or do you move it out a few months to tap into momentum? To make these decisions you need to have an open and trusting dialogue with your team and advisors. They need to know when to raise it, and you need to know what your options are.

Setting compelling focus areas helps make it easier for us to:

• Channel the right direction when we’re losing motivation
• Work on the right things instead of just working on things
• See what we’re impacting when we need to make choices

Effective prioritization happens by constantly asking questions of ourselves and each other that help get the team down an a common, aligned set of focus areas that adapt to new information AND tap into the best of each team member.

Decision Four: Key Plotline

I am struggling to sell my vision of what needs to happen to the people I need to make it happen

It’s great that you know what you’re working towards, but what about everyone else? How do you get there? And how do you know it had the impact you wanted?

You need to connect the dots from those ideas you created to the work that will enable it, the story that will sell it, and the data that will help you know if it had the desired effect.

You need different story-telling languages because you have different humans around you.

You create resonance by listening to your customers, your loved ones, your advisers, your critics and your team and turning it into different ways of sharing and co-creating the vision:

• Metaphors & images communicate intent and simplify
• Examples make it real for those that don’t see the direction clearly
• Data ensures you go in eyes wide open and can take the emotion out of things
• The journey can catch people up to where you are
• Goals give people a more certainty so they can craft plans
• Plans that are nimble to change give clarity to everyone when brains go on autopilot

If you find there’s a language that you can’t get command of and you need to to move your business forward you have some choices.

• Practice makes perfect
• Engage others with strong command of that language and let them help build the story

As a teenager I was part of a writing club and we would do assignments. You have 10 minutes to write something, anything, about a hamster — go. I learned very quickly that while some products are better than others, you can tap into inspiration on command by practicing being inspired.

Whether you’re partnering, practicing or both — you will need to learn to let go of perfection and learn to create. Ideas of what something “should” look like are often the heaviest anchors we wear. It keeps us from trying things we aren’t familiar with, getting critical feedback, and creating something greater than we could create ourselves.

At this point, everything should fit on one page. If it’s not there, I challenge you to get there. It will be practicing prioritization.

Decision Five: Choosing Focus

I know what I need to do but I’m struggling to do it

We all get stuck or distracted. Getting ourselves refocused and unstuck is the art of making a plan a reality. I have one piece of advice for that.

Be intentional.

• Make early progress – it will fuel you and provide inertia
• When you run into a brick wall – unpack it
  • Do you need to turn around?
  • Go around it, scale it, break it?
• When you’re worn out – feed yourself
  • Refocus on what’s on the other side
  • Take a break, rest or reward yourself
• Every week – reflect and reorganize for a few minutes, review your plan, calendar and lists and ask yourself four questions:
  • Are you where you need to be?
  • Did you spend your energy last week where you needed to?
  • Do you need to make adjustments to next week to use your energy wisely?
  • Do you need to change the plan, measures or priorities?

In mindfulness meditation, the big “aha” moment I had is when I realized that focus is not the goal. The beauty is in learning to identify you’ve lost focus and pull it back to center – without judgment. By doing that you grow the parts of your brain focused on attention regulation. You build a muscle.

That same level of acceptance is how you approach focusing on what matters the most. The magic isn’t in perfection. The magic is what happens when you learn to recognize the loss of focus as just a natural part of the process. Accept it, and pull it back to center.

When you take the journey, you’ll find the results you are looking for.

Want some help?

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