Your 2027 Plan Has to Account for the Person Running It

A useful annual plan connects what you want to accomplish with how you lead, spend your time, and keep your commitments.

Open your calendar from last week before you open a blank document for next year. Look at what received your attention, what was interrupted, and what never made it onto the schedule.

Now compare that week with the goals you keep talking about.

You want a team that takes more ownership, but every decision still comes back through you. You want to be more present at home, but the last hour of the workday keeps expanding. You want time to think, but you have filled every available opening with another obligation.

Those gaps deserve a place in your annual planning.

I want you to set ambitious goals. I also want you to examine the way you operate before you ask the next twelve months to produce a different result.

A bigger target may require a new hire, more capital, or a better process. It may also require you to stop rewriting everyone’s work, have a conversation you have avoided, or accept that you cannot personally control every outcome.

If your plan leaves those things untouched, you may be asking an unchanged pattern to deliver a different life.

Start with a week you actually lived

Your calendar gives you something concrete to examine. Instead of judging whether you are a disciplined person, look at where your hours went and what those choices made possible.

Choose an ordinary week, not a vacation or an unusual deadline. Mark the time spent on work that genuinely required you, work someone else could eventually own, and commitments outside the business.

Then look for the promises that were displaced. Perhaps a workout disappeared when a meeting ran long. Perhaps dinner with your family became another evening of answering messages. Perhaps the strategy session you scheduled with yourself was the first thing you canceled.

I would not turn one week into a verdict about your character. Look for repetition across several weeks. A genuine emergency and a recurring habit require different responses.

Next, ask what would have to change for your stated priorities to survive an ordinary busy week.

That question forces a useful level of detail. More family time might require a different client response policy. More thinking time might require shorter meetings or fewer meetings. Better health might require arranging appropriate care and protecting the time to follow through.

Your plan gets more useful when it describes those conditions. A promise without space on the calendar still has to compete with everything already there.

Find your part in the recurring problem

Consider a business owner who wants the team to take more initiative. The annual goal says to develop stronger leaders and delegate more responsibility.

That sounds reasonable. Now suppose the owner routinely changes completed work without explaining why, asks to approve small decisions, and takes difficult client conversations back from the person responsible.

The team’s hesitation deserves a closer look. Before making initiative a hiring problem or a training problem, the owner needs to examine what happens when someone actually exercises it.

This is where I want annual planning to get personal.

What do you do when someone makes a decision differently from how you would make it? Can you explain the standard clearly enough that another person can meet it? Are you willing to let them learn within reasonable boundaries?

You may discover that you have delegated tasks while retaining every meaningful choice. If so, writing “delegate more” on next year’s plan leaves the hard part unresolved.

Make the change observable. Choose one decision another person can own. Define the limits, the situations that require escalation, and when you will review the result. Then notice whether you honor that agreement when you feel the urge to step in.

You do not need to blame yourself for every problem in the company. You do need to be willing to identify the part you can change.

Plan across the life your business affects

I use the Five Bridges to make sure the conversation reaches beyond the business: Spiritual, Internal, Relationships, Environment, and Legacy.

Each gives you a different way to examine what you are building.

The Spiritual bridge asks about faith, purpose, and the convictions shaping your choices. The Internal bridge asks about your discipline, your character, and how you respond under pressure. The Relationships bridge brings the people closest to you into the picture.

The Environment bridge asks whether your health, finances, physical surroundings, and systems support the life you intend to live. The Legacy bridge asks what your choices are adding up to and what you want others to experience because you were here.

Take one business goal and walk it across all five.

Suppose you want to expand into a new market. What purpose does that expansion serve? What will it require of your energy? How much travel will it add, and have you discussed that with the people affected? Who can carry the added responsibility? How does it fit the contribution you want to make over time?

You may still choose to expand. You may change the timeline, strengthen the team first, or decide the opportunity is not right for this season.

I want you to make that choice with the consequences visible. The people at home should not discover the real demands of your annual plan after the commitments have already been made.

Give each priority a behavior and a tradeoff

Once you know what matters, decide what you are actually going to practice.

A goal to become less involved in daily operations needs specific decisions you will stop making. A goal to strengthen your marriage needs attention both people agree is useful. A goal to improve your financial position needs a clear picture of the numbers and choices you are willing to make.

For each priority, write three lines:

• The result I want to see.
• The behavior or decision I will change.
• What I will stop, reduce, or hand off to make that possible.

Be honest on the third line. If everything on your current schedule remains and every new goal adds another commitment, you have more work to do on the plan.

Then bring the time frame closer.

What needs to be true by the end of the first quarter? What can you do in the first month? What needs to happen before that first action is possible?

You might need a conversation before a handoff, a handoff before a protected afternoon, or reliable numbers before a financial decision. Put those steps in order instead of making the final outcome your only measure of progress.

Finally, choose a review date. Check what you did, what changed, and what you learned. If the plan is not working, investigate before simply demanding more effort from yourself or everyone else.

The goal is to have something you can use when the week gets crowded.

Action Items Before You Finalize Your Plan

1. Review three ordinary weeks from your calendar. Identify one repeated conflict between what you say matters and where your time goes.

1. Name a recurring problem you influence. Write down one behavior of your own that may be keeping it in place, without assuming you are the only cause.

1. Choose three priorities: one personal, one business, and one relational. Define what meaningful progress would look like for each.

1. Give every priority a behavior and a tradeoff. Identify what you will do differently and what you will stop, reduce, or hand off.

1. Discuss the plan with someone affected by it. Ask what you have overlooked, then set a first-quarter checkpoint and a first-month action.

Three Five Bridges Challenges

• Spiritual: Take one major goal into prayer and examine why you want it. Where does it reflect a genuine responsibility, and where might you be seeking approval or avoiding something difficult?

• Internal: Choose one response you want to change when pressure rises. Describe what you will practice instead, such as asking a clarifying question before taking a task back.

• Relationships: Ask someone close to you what they hope will be different next year. Listen long enough to understand their answer before explaining what your business needs.

Make Time for the Decisions

You do not need to predict every problem 2027 will bring. You can decide how you want to lead, what deserves protection, and which habits you are willing to examine before another year fills up.

Start with the week you actually lived. Build a plan that accounts for the person who will have to carry it out.

If you would like to work through this with me, 2027 By Design takes place October 21, from 11 AM to 3 PM Central at Five Bridges Farm in Oregon, Wisconsin. Registration closes Friday, October 16. Whether you join us or work through these questions on your own, put time on your calendar to make the decisions.

Inspire & Impact,

Josh