Jump Start the Change You’re Looking for: A 5-Step Plan for Your Own Personal Retreat

Jump Start the Change You’re Looking for: A 5-Step Plan for Your Own Personal Retreat

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While hiking with a group of friends the other day, my girlfriend mentioned that she’d just returned from a posh “personal development retreat”— a professionally-run program focused on R&R, discovery, and action. These kinds of programs have become popular nation-wide, trendy even, and for anyone looking to jump start a positive change in their lives, these kinds of experiences can have a powerful impact. The problem for most of us is that they also typically come with a powerful price tag (usually upwards of $1000, especially where I live in Silicon Valley).
The good news is that you can obtain these same benefits at a fraction of the cost by organizing your own personal retreat experience—and in this article, I’ll outline the 5 easy steps to developing a successful and fulfilling retreat that will jump-start the change you need in your life.
As you follow along you’ll notice “Coaching Questions” listed for each step. I recommend either discussing them with a friend, or writing your responses in a journal or notebook. Once you complete your retreat, revisit your responses and note what you learned about yourself and this process.

Step 1: Ask “Why?”

To truly maximize the impact of any potential solution, first make sure it’s well aligned with what you really want or need. Get clear on the motivations you have for doing a retreat, and also get clear on the baggage you might be bringing into it. Acknowledge the struggles you’re facing and consider whether a retreat in particular will help you work through those issues.
Don’t feel like you have to be sure that a retreat is the perfect next step for you. This step is designed to surface the assumptions you might be holding about why this option will work at this point in time. That way, as you proceed, you can test those assumptions and better understand what will work best for you in the future.
This step will also help surface any preparation that might be necessary before proceeding. In my case, for example, I suffer from panic attacks, and the knowledge that I would be spending a lot of time alone was very difficult for me. I decided to schedule some targeted sessions with my therapist to prepare.

Coaching Questions for Step 1:

  • Why are you interested in a personal retreat?
  • What struggles do you have that you hope a retreat will help you with?
  • What do you hope a retreat will provide you with to help you in the short term? Long term?

Step 2: Set a Goal.

A goal should clearly state what you want to accomplish by the end of the retreat. A goal does NOT state what you will DO during the retreat.
Feel free to set one big goal or 2-3 small ones. Consider these five elements of a good goal statement:
  • Specific: Avoid vague statements like “I want to feel happy” or “I want to enjoy myself”. Aim for measureable and targeted goals like “I want to lower my daily stress level from a 10 to a 5” or “I will be able to stay focused on a difficult task for an hour straight”.
  • Measurable: By the end of the retreat, you should be able to review your goals and clearly state “Yes, I accomplished that,” or “No, I did not accomplish that.
  • Attainable: Make sure your goal is something you can actually influence. For example, I wanted to spend time working on my relationship, but I can’t do that alone. I could, however, set a goal to improve things that I have control over, such as how I react to my spouse when I’m angry or frustrated.
  • Relevant: Be sure to pick a goal or goals that are consistent with the purpose of the retreat (e.g., “finish laundry” might be an important todo, but less relevant to the actual retreat planning)
  • Time-bound: Make the goal appropriate for the time you put aside. Don’t set a goal to get in shape or write a whole novel if you only have a week.
Keeping goals specific, measurable, actionable, relevant, and time-bound prevents us from getting discouraged and also makes it easier to tell whether we are successful or not (and it’s okay not to be!) Any progress you make forwards or backwards (yes, failure is progress) is learning that will better illuminate your path going forward.

Coaching Questions for Step 2:

  • What does success look like to you for this retreat? What specifically do you want to accomplish over this period of time?
  • How will you know if you’re successful?
  • Tip: Be gentle with yourself, you can’t (and don’t want to) change everything overnight!

Step 3: Identify Barriers.

Once a goal is set, resist the urge to jump straight into planning the details of what you’re going to do. While you’re probably excited and ready to go, you risk ignoring an important consideration: what might get in your way. By taking time to consider potential barriers, our plan can take them into account.
Consider both what you might struggle with in regards to achieving your goal as well as with the actual experience of a retreat. As you think about the barriers and challenges you might face, also take the time to identify what might help you in those tough moments. These can be incorporated into your plan!
For example, I know that I struggle with wanting to give up whenever something is really hard for me, and this could potentially put the whole retreat at risk. It was important for me to acknowledge and prepare for this while making plans for all the cool things I wanted to do, many of which I knew would require a willingness to struggle and/or fail.

Coaching Questions for Step 3:

  • What are some existing personal/emotional/mental barriers you typically face in the process of learning/self-reflecting/etc.? What are some insecurities or anxieties that could surface throughout this process?
  • What are some things that might get in the way of finishing your personal retreat?
  • What are some things that might get in the way of achieving the goal that you set?
  • What might you need or want to help you through these tough moments? Is there a mantra, a person, an activity, or a resource that typically calms you or helps you to push through?

Step 4: Make a Plan.

Phew! Finally it’s time to get planning. This is my favorite part. I love figuring out structures, schedules, and details of what I’m going to do and when. An important caveat, however – a plan is not, and will never be, perfect! Things will change, and if you go into this thinking that you have to stick to every single piece of this plan, you may end up disappointed and that is something we want to avoid!
Make a plan that includes as much structure as you need for your retreat. Consider your barriers from Step 3 as well as your general preferences.
For example, I generally need structure to help me fight through indecisiveness, but I also prefer to follow my mood, so my plan involved giving myself options for each part of the day so that I could stay flexible.
Be sure to keep things manageable and enjoyable! Build in time for relaxation, creativity, self-reflection, physical activity, and being in nature. These activities support your wellbeing, and will help you stay focused for other more intense activities you might want to do like writing or taking a class. Also consider adding activities that you’ve always wanted to try or things you used to enjoy but haven’t done in a long time to push your comfort zone a bit.

Tips for Planning:

  • Put aside some time before the retreat to prepare in order to limit commitments to others and responsibilities around the house/work as much as possible. Buy groceries or do laundry ahead of time, arrange for a baby-sitter, or talk to a partner or friend about helping out with errands during your retreat.
  • Build in time for the things you absolutely can’t avoid. Maybe there’s an appointment or a work dinner you can’t reschedule. Make them a part of the plan and work around them.

Step 5: Retreat!

Now that you are on your way, be sure to check in with yourself regularly throughout the retreat. Remember that eating well and getting a lot of sleep will help you maintain a strong mental and emotional state and will set you up with the most potential for success.

Coaching Questions for Throughout the Retreat:

  • Each morning/At the beginning à How am I feeling about my plan for now/today? What might I change based on how I’m feeling or based on what I know now/learned yesterday?
  • Each evening/At the end à What made me feel proud of myself? What did I learn about myself or this process? What went well, what was a challenge?
Remember that the goal you set is purely a way to provide direction and focus. At the end of the day, reflecting on your path towards a goal will help you learn more about what matters to you, what you like or dislike, and how work through challenges.  
Enjoy yourself! Take care of yourself. Be kind to yourself. Focus on the learning and don’t ever be afraid to ask for help.

Good luck and leave your comments below to let us know what you’re planning for your personal retreat, or to share any tips that you pick up along the way.

Keywords: personal development, career, fulfillment, happiness, goals, how-to
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Anna Kawar is a passionate improvement coach with a decade of experience building the capacity of individuals and teams to continuously improve, personally and professionally. She currently works for the Carnegie Foundation for the Advancement of Teaching where she has taught over 800 educators and coached over 60 teams from non-profits, schools, and districts to use innovation, rapid-cycle testing, data, and spread methodologies to improve educational outcomes for K-16 students. Anna started her career at the Institute for Healthcare Improvement in Boston, where she managed and helped develop a network of almost 500 healthcare improvement experts and fellows. She received her MPP and MBA from Duke University, where she was an Education Pioneers Graduate Fellow and led notable projects with the North Carolina Department of Juvenile Justice and Delinquency Prevention and Triangle Family Services. Anna currently serves as an advisory leadership coach to Full Circle Institute and sits on the boards of Improving Education in Baltimore and the Design Museum Foundation in San Francisco.