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Do you love planning and strategising your holidays?

Do you love planning and strategising your holidays?
Anne Beth Jordan
Anne Beth JordanANNE BETH JORDAN - Business Coach/Mentor

Posted: Thu 15th May 2025

Do you love planning and strategising your holidays, excited when all comes together and off you jet to your dream place?

The dream

I’m just back from 10 days in Naples and Sicily, a bit of a whirlwind. Loved Sicily, didn’t like Naples, except visiting Herculaneum on the outskirts of Naples, and the art galleries up at the top of Naples, away from the frenzy.

I think I planned it well, with the help of my best buddy, whom I travelled with. I must admit he did more of the planning of the trip in terms of days spent per place, how to get from one place to the other, whether to go interrailing, bus or car. We covered a total of about 1000 km over 10 days, so a pretty easy ride.

Anne Beth Jordan on holiday

We planned all our accommodation in advance, choosing our budget per night and looking for the best accommodation, with a little gift to ourselves in a couple of places where we could not resist the décor and paid a higher price (beware of décor being a cover-up for inadequacies).

All seemed to have gone well, and we returned 90% delighted with what we had seen and done. Loved Sicily for its wonderful coffee and food, architecture, (almost throughout I felt I was in a living museum, locked in time), the Sicilian Highlands covered in spring wildflowers, and we had a wonderful ‘godfather’ moment as well.

Would our holiday have been as successful if we had not put our strategies and plans in place and just rocked up at Naples airport, without a clue of how to get around etc?

Maybe yes, maybe no. We were both adults, well-travelled and had a sense of the world around us. But we didn’t want to take a chance, we wanted to ensure a smooth experience and leave hassels behind us for a few days.

Watch this webinar to learn the difference between a mission statement and a vision statement and how they can help your business grow:

Some tips and ideas for start-ups and beyond

When strategy and planning are well thought out, they can make a difference to one's personal and business hopes, dreams and goals.

From my personal experience, not just in business but in my everyday life, using strategy effectively comes down to setting myself clear goals, keeping plans simple and staying flexible in the face of change.

It starts with having a clear vision, builds on a solid plan (mission – your purpose, your everyday working which helps you achieve rhythm and focus).

Just a little note on the difference between planning and strategy:

For me planning is like a road map for getting things done.

Strategy is the ‘how’ and ‘what’ you choose in order to achieve your objectives that set you on the path of your road map.

Helpful steps to take as you create your strategic plan

Define clear and shared objectives

  • SMART goals: Set objectives that are specific, measurable, achievable, relevant and time-bound. These provide you with a clear and motivating target to work toward. If you already have a proven way of achieving your goals, please continue to use that method

  • Alignment: Keep your goals relevant with your vision and mission (check that your current vision and mission are still relevant, or does one or the other need adjusting).

    Breaking down your mission into easy and manageable steps will help you to get to your vision. The strategic actions you put in place are the glue that binds the mission and vision together.

    This ensures that everyone in your sphere feels connected to the same big-picture outcome

  • Clarity: Make sure everyone in your sphere understands the objectives and how their contributions matter. A shared understanding eliminates confusion and keeps everyone moving forward together

Plan thoughtfully

  • Formalise strategy execution: Develop a detailed plan for how the strategy will be implemented. This should include assigning responsibilities, setting timelines and identifying resources

  • Build your plan: Create a detailed roadmap with action steps, timelines and resources that will guide you toward your goals

  • Explore options: Weigh your choices and pick the strategy that feels right for your goals and the resources you have available

  • Think ahead: Look out for potential risks and make thoughtful decisions based on what you know about the situation

Execute and stay flexible

  • Make it happen: Put your plan into motion, ensuring you have all the tools, resources you and your team need to succeed

  • Check progress: Keep an eye on how things are going and adjust your approach as new information comes in or circumstances change

  • Stay adaptable: Flexibility is your strength! Be ready to turn around if need be, if things don’t unfold as expected. You never know what is around the corner, unless you have fully prepared yourself, and even then, there may be a 1% chance of having to look into the magic ball

Don't complicate

  • Keep it simple: Complicated strategies can trip you up. Aim for simplicity to stay on track

  • Work together: I’ve added this in case you are at the stage where your business is no longer just you. Involve your team in shaping and carrying out the strategy. Shared ownership means stronger commitment and accountability

  • Communicate often: Keep everyone in the loop with clear and regular updates on your strategy

  • Improve continuously: Regularly review your strategy and refine it to make sure it’s working the way you need it to

Key takeaways

1. Clarity and simplicity are essential

  • Clear goals, both personal and professional, form the foundation of effective strategy

  • Use SMART goals (Specific, Measurable, Achievable, Relevant, and Time-bound)

  • Simplicity in planning ensures your strategies are easier to follow and execute without unnecessary complexity

2. Strategy and planning serve different roles, but work together

  • Strategy focuses on the "what" and "how" to achieve objectives. It focuses on direction and key decisions

  • Planning acts as the "roadmap", outlining specific steps, responsibilities and timelines to execute the strategy

  • Together, strategy and planning ensure that your vision, mission and actions (strategies)are aligned for success

3. Flexibility and continuous improvement lead to success

  • Staying adaptable allows for adjustments when circumstances change

  • Regularly review and refine strategies to ensure they remain effective and relevant

  • Involve your team and maintain strong communication to foster shared ownership and accountability

  • Take time out for yourself to step back and create a checklist. This could help with keener decision making, better choices and peace of mind

I hope you found this helpful, particularly as you begin your new business start-up and journey. Constantly giving yourself time and space to step back, think through your decisions and actions required to fully optimise your time available in your busy working life. I feel that creating effective strategies and putting them into a cohesive plan will bring you greater success and peace of mind.

Relevant resources

Anne Beth Jordan
Anne Beth JordanANNE BETH JORDAN - Business Coach/Mentor

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