Lost in Transition? Try the ‘Tough Cookie 100-Day Plan for Getting Unstuck’ (Over 30 Ideas)

Time keeps on telling me who to love, where to go. Time keeps on pushing me further on down the road. -- Lyrics from "Time" by Josh Rouse
Time keeps on telling me who to love, where to go. Time keeps on pushing me further on down the road. — Lyrics from “Time” by Josh Rouse

There are only two types of people in the world: people who do what they say they’re going to do when they say they’re going to do it, and people who don’t do what they say they’re going to do when they say they’re going to do it.

I am the first type. I do what I say I am going to do. Unless, of course, I’m stuck. I hate getting stuck.

All of us, despite best intentions or track records of follow through, often find we’re lost, confused, undecided, doubtful and ambiguous. We’re frozen in place in the larger context of life, even as we manage to look busy and ooze a pretend-kind of happy.

When it comes to inventing life – a new or continued career, different view out the window, ways to make money, different people to hang with, better focused choices, more engaged productivity – the whole darn thing is daunting.

We think about how we might change. We think how life could be even better. We think we should start thinking about our last third of life.

Time passes and we drift around in our thoughts.

It’s not you that’s the problem. It’s the process.

Get Out of Your Head

More often than not the lack of action is because we lack clarity.

This uncertainty about how to figure out a life and make it happen mounts if you continue to follow old self-help advice doled out by experts:

  • Find your passion,
  • Work your strengths
  • Discover your purpose (Oh, Lordy)
  • Write that damn mission statement

I rant and rave about these once-inspiring ideas often. Passion, for instance, is desire, lust, and craving. My high desires for designer clothes, weeks at sea, a calendar full of National Geographic Expeditions, standing ovations and beautiful produce from Farmer’s Markets delivered to my door are part of who I am.

I love my passions! But, passions rarely pay bills (skills do) and don’t make a good map for a productive life that sustains happiness.

Interests, beliefs, actions shape an engaged, full life, not passions.

Following old advice means ending up with the written word in numbered lists, in journals, on mind maps or parceled out in tiny statements meant to encompass an entire life.

Most of us have engaged in enough head work to fill a steamer trunk. Enlightening at this stage of the game? I think not.

Ready to hear something different? I hope so.

 You throw an anchor into the future you want to build, and you pull yourself along by the chain. --John O’Neal

You throw an anchor into the future you want to build, and you pull yourself along by the chain. –John O’Neal

 Just Be Doing

This is about answering an old, unavoidable question in a new way. No matter who you are, how old you are or how successful you’ve been, you will find a place after 50 when you are unsure about the path ahead.

A big booming voice will say, “What are trying to do with your life?”

I was in a scramble and lost when the question came barreling down on me.

It’s tough enough being lost.  Stumbling around in neighborhoods in Buenos Aires even as Citymaps clearly plots my location on my iPhone screen, I often have to walk a ½ a block until the arrow starts moving so I know what direction I’m heading.

But let’s talk about the deeper meaning of lost. Explain to yourself how to live your best, most fulfilling life. This isn’t easy.

But it is absolutely possible to design your future life  – one to thrive along with your age and time left.

To launch anew, Herminia Ibarra tells us to “get out of our heads.” Ibarra is the Cora Chaired Professor of Leadership and Learning at INSEAD in Fontainebleu, France and the author of “How to Stay Stuck in the Wrong Career.” (Harvard Business Review ONPOINT, Summer 2015.)

Ibarra jettisons most of what we know about career and life transitions. She asks us to consider that the traditional “plan and implement” approach actually fosters stagnation. You get mired in introspection while searching for something that’s unclear.

These ideas provide a firm-footed foundation for getting unstuck in one of life’s most difficult transitions – mid-life to late-in-life adulthood. We simply over-think.

Your ‘tough cookie’ voice demands action.

This is about doing – sometimes without clarity; perhaps based on intuition or curiosity; seemingly illogical; possibly grandiose; logical (meh); or bold and scary.

You may not like her music, but little Taylor Swift has the music industry on its tail. Fortune released their “World’s Greatest Leaders List” with Taylor at No. 6 behind a CEO, a few presidents a prime minister and the pop.

Her 1989 reveals an artist in transition and definitely felt like a risk for Swift. Interviewer J. Rentilly calls her the “hottest country star who changed up everything.” (Southwest Airlines, The Magazine, May 2015.)

Making a pop album after doing four country albums is the boldest thing I’ve done recently. No one at my record label understood why I wanted to fix something that wasn’t broken, but I was following an intuition – not the intuition of men in suits in a conference room, but my intuition.

That’s probably the boldest thing any of us can do – listen to what our gut is telling us.  -Taylor Swift

But it’s intuition with an action plan that moves Swift along. She pivots and shakes it up. She’s a doer.

If you feel stuck or if you are interested in getting a head start in life design Post50, you’ll want to take action – do a little pivot. (Or big pivot?)

If you feel slightly crazed as a slacker in life and can’t figure it out. If your feel slightly out of sorts about the future. If you feel unclear. Well, let’s rotate your axis for a new perspective.

Maria sets up her booth each Sunday in the same place at the San Telmo Flea Market in Buenos Aires. She writes down what she sells in her book which she was happy to show me. Some Sundays she doesn't sell anything.
Maria sets up her booth each Sunday in the same place at the San Telmo Flea Market in Buenos Aires. She writes down what she sells in her book which she was happy to show me. Some Sundays she doesn’t sell anything.

Surrender to the Act of Doing

Do something. Then do something else. Then do something else.

Do three of the activities suggested below in The Tough Cookie 100-Day Plan for Getting Unstuck all at the same time.

Just be doing.

Fashion designer, Bruno Cucinelli’s beautiful, unaffordable clothes carry a small, hip torn-edged booklet.

From inside:

“product of quality

fruit of our labour

is created in Solomero

a small medieval village

at the gates of Assisi

where Men and Nature

are still aware

of the harmonious rhythm

of Time.”

The essence of getting unstuck especially after midlife is about time – the rhythm of time in our lives.

Either you are going to be a part of creating a new rhythm or time as singer/songwriter Rouse reminds us  . . .  Time pushes you further on down the road.

Constructing a life is about focusing on the core of your individuality and what matters to you. With hard work, course correction and new way points, this focus will lead to the most meaningful experiences, the most enriching work and the most fulfilling life you could have.

Isn’t that worth 100 days?


100-Day Tough Cookie Transition Plan

Directions: Pick three things and take action in the next 100 days. Each activity constitutes a lesson plan to increase self-awareness, deepen knowledge of desire and add information you don’t have now. Some activities take 100 days; others less time; many can be repeated.

Doing comes first; understanding and learning second. Do one if that’s all you can undertake right now or do them all. Use them as inspiration to make up your own ideas.

  1.  Craft a story of who you are now; then craft a story of who you want to be. Record it. No writing it down. Listen and tell me what you hear. My response is, “What’s up now?” Answer the question.

  2. Interview three people who transitioned out of your industry to an entirely new career. What was their thought process? How did they do this? What were the challenges? If you only have one person who fits this criteria, do that interview but ask at the end, “who do you know with a transition story I might talk with.”

    3.  Allow someone or a group to interview you asking as many these questions as you can bear: Your regrets so far. What you would do if money didn’t matter? Where have you always wanted to be in life? What’s not in your life that you want? Where are you versus where you thought you would be? What are you proud of and what could make you more proud? Ask them to tell you what they hear you saying. Ask them what they see as the most important step to take. This may freak you out but do it anyway. I call this experience “the hot seat” and it’s powerful as many executives who’ve done this will attest.

    4. Find a “fresh” group of individuals with a focus on your interests or one focused on professional networking. Professional Meetup Groups are worldwide. How can you get to one of their meetings? One may not be in your home town. If it is a 100 miles away, so be it. Go.

    5. Collect articles, pictures, news items that for some reason you don’t understand speak to you. Something  – a message, curiosity, interest, visual attraction – captures your attention. Collect randomly – online and in print – and intentionally for 100 days. Store print in a binder; store online in a folder. On the 100th day spend 2 hours sorting into themes. What do you see? Identify themes and core interests. (This activity was one of the most enlightening and proved to have much merit in my getting unstuck in my 60s.)

    6. Attend an industry meeting or conference. It doesn’t matter if you already left that industry or don’t know a thing about a new industry. You want to learn.

    7. Go where you can be alone – for a day or a month. An inspiring place. Camp, stay at the Ritz, ask to go to your friend’s shed in the mountains that’s usually vacant in the winter. Be alone. Talk to yourself. Answer all those questions in “the hot seat interview,” #3.  You don’t need to journal. If you are intent and listen, direction will surface.

    8. Find four objects that are symbols of your success in life. Each one is specific and important to you. Put them on your desk. Now, take two away. Go find new objects in the coming days that symbolize a greater fullness to your life and to your being. This is life in the future. How does it look? What do you need to do?

    9. Engage in something for the first time. Paddle board, go into a fancy restaurant by yourself and dine, start a garden, change a sprinkler head. Get excited about something and do it.

    10. Declare a major and minor for a seasoned semester of joy and enlightenment.For example, “Major in Technology; minor in Biking.” Craft your calendar with those activities as priority.

    11. Prospect for a better life. Visit a new area you’ve thought would be a good place to live, reconnect with a college friend who seems in a better place than you or travel solo in a group of like-minded people to a place that interests you or better yet, makes your heart pound.

    12. Research phased retirement to see if this is a good option. Start here.

    13. Start your day with this question: What is one step can you take this week to get you unstuck? Write it with lipstick on the mirror in your bathroom. Tell the cleaning ladies not to touch it. I promise it will last 100 days.  When you’ve got a good answer, take that step. Then tell the maids they can clean the mirror.

    14. Take 2 sheets of white copy paper. Write your birth date on one; write your anticipated departure date on the other. (Guess). Collect 15 index cards in the same color. Tape on a wall in this order: birth date, index card, departure day. That index card is the dash – the time between two life events. You are living the dash everyday. Take the other 14 index cars and put them where in places you’ll see everyday… in your car, closet, on the toilet, on the garage door, on your iPad cover. Be thinking about that dash for the next 10 days. There should be a plan for that dash. What’s your plan? What do you need to do soon?

    15. Buy some colored jelly beans. Pick the one that makes you want to vomit. Roadtrip Nation calls this your “vomit-flavored jelly bean” but they use it to induce creativity. In this exercise, it symbolizes every thing that makes you sick about your life. This is the ho-hum part of your life.  Take that jelly bean and put it where you can see it everyday. When you diminished or eliminate at least 4 things that make you sick or bore you death, throw the jelly bean in the trash. (Idea adapted from a terrific book that you should buy even if it’s target audience younger than you. RoadMap, by Roadtrip Nation.)

    16. Select five different people who are each earning a living after 60 and seem to be engaged with their work. Have a conversation with them and identify what happened in their time of transition. How did they find or forge a new path? You don’t need to know these individuals. Tell them you’re on a transition journey and want to do it well. Ask for 10 minutes of their time.

    17. Identify a dormant interest. Become knowledgeable with current information through the internet or books. Revisit this interest with an action step or if it’s not that exciting to you anymore – ditch it.

    18. Determine a geographical place that inspires you then go. Act on this whim. I once went to Oaxaca, Mexico because of a picture in a travel magazine. I loved that picture and that trip began a life-long adventure of collecting local art that I treasure.

    With the artist, Ariel Dawi, in front of his painting, Rojo Grande. -- Cuenca, Ecuador, 2013.
    With the artist, Ariel Dawi, in front of his painting, Rojo Grande. — Cuenca, Ecuador, 2013.
    Big Rojo now graces my dining area. Since that visit to Oaxaca years ago, my love for local arts remains strong as you can see!
    Big Rojo now graces my dining area. Since that visit to Oaxaca years ago, my love for local arts remains strong as you can see!

    19. Make a public declaration to someone you respect. Clarify an intention to improve your situation by getting unstuck. Present a plan in 30 days. Ask for feedback; revise; take action; be accountable.

    20. Invent a job in your head or a lifestyle you want. Breakdown the work or the lifestyle into 4-5 areas. Select two possibilities right now to investigate.

    21. Overhaul your lifestyle by cleaning out your calendar. Get rid of all the meetings, memberships, and commitments you’ve made because they no longer fit. It doesn’t bring you joy? Out it goes. Big commitments like leaving the Coast Guard after 20 years of service. Say you’re sorry but your opening up space for other things in your life. Little things, too, like that lunch with a know-it-all that you don’t enjoy. Breathe life into the space you have created.

    22. Determine what one thing you do can do at this point in your life to come to a new understanding of your self? Who are you now anyway? Take an action to find out who you’ve become.

    23. Visit the past but instead of romanticizing the past – a backward tendency – dissect it for the negatives. What three things would you have done differently? How might those actions in hindsight shape what you do in a Post50 life?

    24. Watch three TED talks about something  your interested in or tune into three about individuals who transformed their lives. There are over 2000 TED talks to browse.

    25. Follow one-three people on any social media outlet. Especially read the ‘Comments Section.’ Absorb ideas. Make 20 comments in the next 100 days on each site. What do you know at the end of 100 days that you didn’t know? What did you learn about yourself?

    26. Call me and ask for my ‘tough cookie’ voice. I’d be happy to give your 10 minutes.

    37. Identify your roadblocks. Select your top three. Have a conversation with one of them every day. “Here’s how you are holding me back. Here’s how I’m going to get rid of you.” Take a step toward beating through each one every 30 days.

    28. Create a manifesto of what you believe holds true. (My one concession to writing something down. Here’s mine.) Make it visually appealing. Print or keep it online. Visit your Manifesto frequently for inspiration. If you believe these things, you should be living them. Are you? What should you do differently?

    29. Create your own syllabus – an outline of study to stimulate a interest or improve a knowledge base. Invest in classes, books, author events, online webinars, conferences…whatever it takes. Meet and greet people along the way.

    30. Explore how serendipity has shaped your life. Determine three ways serendipity might look like now? Make a screen saver with these new chances as possibilities for a future life. Examples: I want a chance to live on an island. I want a chance to publish a book. I want a chance to help immigrants. At then end of 30 days, pick one and eliminate the other two. Make a new screen saver with your chosen serendipity. Take 2 steps to inch toward making that chance happen.

    31. Leverage a past positive experience into a current setting. If you loved speaking at industry meetings in your past career, what groups can you be in front of now with a message? I wrote terrific (really they were outstanding) term papers in college. While everyone else in the dorm hated it, I didn’t mind. I’m writing for you now. It makes me happy. What positive experiences can you leverage?





About Barbara Pagano

Barbara Pagano,Ed.S., author and speaker, influenced over 3,500 executives in organizations to achieve higher performance. She is now on a mission to help individuals extend their career arcs and craft lifestyles of productive longevity.
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