99 Questions - A Boomer's Primer For Surviving Transition

The word “crisis” suggests considerable pain and suffering. We all wince at the memory of the crises in our lives: having to choose which college to go to or career to start after High School, getting married, having a child, changing jobs, moving, divorcing, etc. In fact, the word “crisis” is derived from the Greek word “crisi,” which means decision or judgment. The times of our life that demand change and trigger transition force us to evaluate choices and make decisions and judgments. These crisis periods seem painful because they are usually forced upon us by circumstances we feel we cannot control. We are always more comfortable with the status quo we have developed and control. We have a natural aversion to the decision-making involving change. Many of us just don’t like to have to think ahead. But, in fact, the transition periods that confront us with life-altering options can be exciting and energizing. Evaluating our options is the first step in the progressive decision-making process.

Of course, we all know that past decisions that made sense short-term were not always the best ones long-term. But, no regrets. Bad decisions are better than indecision. We overcame all the crisis of the past, grew up, and survived so that we can face the crises of the future, making the short-term decisions that make sense now.

This primer is meant to provide Boomers facing retirement and other live-changing events with the tools to think about transition and making sound decisions that should last a literal lifetime. By designing this initial self-assessment as somewhat of a game, this is one crisis that you will probably have a lot of fun with. You are going to start figuring out who you are, where you want to be in 5 to 10 years, and how you want to get there.

RULES OF THE GAME: CHOOSE AN ANSWER THAT MOST CLOSELY DESCRIBES YOUR CURRENT ATTITUDES AND GOALS FOR THE NEXT TEN YEARS. THERE IS NO CORRECT OR INCORRECT ANSWER. IN FACT, THE MULTIPLE CHOICE ANSWERS ARE SUGGESTIONS ONLY TO GUIDE YOUR THINKING. YOU MAY CHOOSE MORE THAN ONE ANSWER. IT IS A GOOD IDEA TO WRITE IN YOUR OWN THOUGHTS NEXT TO THE ANSWERS YOU CHOOSE. AND REMEMBER -- YOU CAN MAKE A DECISION TODAY AND CHANGE YOUR MIND TOMORROW UNTIL THE CRISIS IS RESOLVED.

1. Are you planning to retire?
(a) Immediatelyn(b) In 1-5 yearsn(c) In 5-10 yearsn(d) I am already retired

2. What circumstance would trigger your decision to retire, if you have not yet retired?
(a) Involuntary decision: reach mandatory age/promotion limitn(b) Involuntary decision: poor healthn(c) Voluntary decision: Miserable work conditions/horrid bossn(d) Voluntary decision: Want to enjoy the rest of my life while I am still “young” and fit

3. How would you describe your energy level as you face the future?
(a) High energyn(b) Strong, but with limitsn(c) Pooped out, but can rallyn(d) Burned out

4. If you know anybody who has already retired, how would you describe them?
(a) Happier than ever with their new choicesn(b) Still vigorously exploring new options but nostalgic for the old status quon(c) Proceeding in slow motion but moving forward towards change n(d) Depressed and miserable

5. How would you compare yourself to a friend or colleague who has already retired?
(a) I have nothing in common with him/her; my circumstances are differentn(b) I have nothing in common with him/her, but I would have made the same choices he/she didn(c) I have a lot in common with him/her, but I would not have made the choices he/she didn(d) I admire the choices he/she made and hope to emulate the way he/she adapted

6. What would you like to do for the next ten years if you could?
(a) Keep working forever in what I know and do bestn(b) Work part-time or volunteer, putting my hard-ea
ed expertise to usen(c) Do something entirely different, develop new talentsn(d) Take a break and do nothing but work on my golf swing and travel the world

7. What would you never like to do again?
(a) Work in a rat racen(b) Work for a rat under any scenarion(c) Feel financial anguishn(d) Have to keep a fixed schedule

8. How much free time would you like to have?
(a) Not much. I am happy when I am busy and productiven(b) It would be nice to have a little more time for myselfn(c) Half a day free at leastn(d) Free time all day long

9. Where would you like to live?
(a) Same house/ town, living on my ownn(b) New house/town near my kids, parents, friends or relatives, living on my ownn(c) Overseas, living on my ownn(d) Senior community with all the amenities and future option for assisted living

10. How is your health?
(a) I eat right and work out every dayn(b) I have a few foibles, aches and pains but take my medsn(c) I need to lose 10 pounds and take my medsn(d) I am a basket case and need to see a doctor

11. How is your stress level?
(a) I am in good balancen(b) I am stressed by big things affecting me (money, health)
(c) I am stressed by little affecting me (traffic, rude people on lines at the supermarket)
(d) I am a basket case and stressed by everything (world events, politics, environment)

12. What do you do to reduce/prevent stress?
(a) Adjust diet, exercisen(b) Sleepn(c) Make lists of priorities, things to don(d) Seek empathy from friends or family

13. What is your attitude towards other people?
(a) I get positive energy from everyone and seek interactionn(b) I get positive energy from almost everyone and engage in relationships when approachedn(c) Almost everyone saps my energy, but I engage in relationships when approachedn(d) I mistrust people and would rather be alone

14. How do you assimilate information?
(a) Facts received first-handn(b) Details researched second-handn(c) Subjective assessment of patterns in the big picturen(d) Intuition into motives behind the events, facts

15. What is your attitude about your age?
(a) I am still a kid at heart and lie about my agen(b) I need plastic surgery and a hot sports car before I can feel better about myselfn(c) I know a lot about a lot and demand the respect that I earnedn(d) I am comfortable in my skin, sagging though it may be, and boast about my age

16. What is your attitude about your past?
(a) I am proud about who I am and what I have accomplishedn(b) I have a lot more to do before I can leave the legacy I would liken(c) I could have done more and know there is always room for improvementn(d) I am a basket case

17. What is your attitude towards your future?
(a) I feel anxiety because the future is unpredictable and I can’t control it or adapt to itn(b) I feel anxiety because I am not sure I can adapt to the futuren(c) I am confident that I can meet the challenges of the unpredictable futuren(d) I am energized by the unknown and am having fun pushing my limits

18. What is your attitude about life in general?
(a) I love every minute of life and have suffered no major traumas, so I am ready for moren(b) I love every minute, but have taken a lot of knocks, so I am not that ambitious n(c) I have taken a lot of knocks and am just too tired to get back in the race againn(d) I haven’t done everything I wanted to, and I don’t see the point of all the effort any more

19. What is your attitude about death?
(a) Never think about itn(b) Know it is inevitable but don’t like to think about itn(c) Embrace religion and other spiritual guidance on the subject
(d) Draw on my optimism to fuel my energy level up and keep a smile on my face to the end

20. How confident are you in yourself?
(a) I have faith in a higher power to take care of men(b) I have faith in myself to do what is necessary to find my wayn(c) I have little confidence that I have the strength to do everything expected of men(d) I am a basket case

21. What is your attitude regarding your significant other, if you have one?
(a) We are a team, in love forevern(b) We are a team, comfortable with each other, but the spark of love is gonen(c) We are at odds with each othern(d) I would be happier alone

22. If single, what is your attitude towards finding a significant other?
(a) I go out on dates and am looking for a permanent, meaningful relationshipn(b) I go out on dates and am not looking for anything permanentn(c) I rarely go out on dates and, when I do, I don’t expect muchn(d) I never go out on dates

23. How greatly does your significant other, if you have one, influence your decisions?
(a) We consult on everything and I take his/her ideas on board before decidingn(b) We consult on everything, but I make my own decisions in the endn(c) I make my own decisions without consultingn(d) He/she tells me what to do

24. Do you socialize with friends?
(a) All the timen(b) Sometimesn(c) Rarelyn(d) Never

25. Do you go to meetings of any clubs/associations/church groups outside of work?
(a) Regularlyn(b) Frequentlyn(c) Infrequentlyn(d) Never

26. What is your attitude regarding the younger generation?
(a) They know nothing and think they know everythingn(b) They know nothing, so I want to protect them and teach them all I known(c) They know a lot and I have a lot to learn from themn(d) I love their music, movies, and lingo and try to fit in with their crowd

27. What do you think about the younger generation’s work ethic?
(a) They are not as loyal to the employer as we weren(b) They don’t climb corporate ladders, but move from job to job to get aheadn(c) They won’t work overtime to get a job done the way we didn(d) They work just as hard as we did

28. What has your experience working with the younger generation? n(a) They don’t appreciate wisdom or training from veteran colleagues n(b) They didn’t seem comfortable socializing with veteran colleaguesn(c) They are not as literate or polite as veteran colleaguesn(e) They welcomed me in their group and were excellent colleagues

29. What do you think about working for a younger supervisor, if you did or might have to?
(a) He/she was a naïve jerk, so he/she deserved no respect n(b) He/she was a naïve jerk, so I was careful to humor him/hern(c) He/she was a naïve jerk, so I tried to provide guidancen(d) He/she was capable and knowledgeable, so I followed his/her guidance

30. What do you think about technology?
(a) I can’t live without my Blackberryn(b) I am used to a paperless officen(c) My vision is not good enough for me to use my Blackberryn(d) I print out everything and use my trusted agenda book and paper filing system

31. What is your attitude regarding children age 0-10 in general?
(a) They are spoiled brats n(b) They are bright but distracted by TV and consumerismn(c) They are receiving an inferior educationn(d) They are angels

32. If you have grandchildren, what is your attitude towards them?
(a) They are spoiled bratsn(b) They are bright but distracted by TV and consumerismn(c) They are receiving an inferior educationn(d) They are angels

33. Do you have hobbies?
(a) Golf, tennis, gym, sailing, etc. that cost a feen(b) Biking, photography, fishing, painting, etc. that does not cost a fee but costs equipment/materialsn(c) Jog, walk, garden, etc. that does not cost anythingn(d) Create art, pottery, sew, etc. that I can sell

34. Do you volunteer?
(a) Regularlyn(b) Frequentlyn(c) Infrequentlyn(d) Never

35. On what do you base your decisions?
(a) Trusted logic based on facts or principlesn(b) Trusted emotionsn(c) Subjective projection of personal consequencesn(d) Whatever is recommended by an author I read/TV personality

36. How open minded are you?
(a) Free thinking and spontaneousn(b) Change mind easily in response to new datan(c) Plan everything ahead of time, deadline orientedn(d) Judgmental regarding outcomes; don’t like surprises

THINK YOU KNOW ABOUT YOURSELF? LET’S MOVE TO THE NITTY AND GRITTY OF YOUR TRANSITION:

37. How would you describe your finances?
(a) I have plenty of savings, so don’t have to work after I retiren(b) I thought I had enough savings, but I am panicked by the economy and need more incomen(c) I have some savings but some debt and need more incomen(d) I am a basket case and need more income

38. What amount of savings, including IRA and 401K, do you think is enough to last you the rest of your life?
(a) $1 million cash for a couple, generating 8% per year = $80,000 before taxesn(b) $500,000 cash for a couple, generating 8% per year = $40,000 before taxesn(c) $250,000 cash for a couple, generating 8% per year = $20,000 before taxesn(d) $100,000 cash for a couple, generating 8% per year = $8,000 before taxes

39. How much do you think you will get in Social Security benefits if you retire at age 65?
(a) Over $5,000 per month after taxesn(b) Between $3 and $5,000 per month after taxesn(c) Between $1 and $3,000 per month after taxesn(d) Between 0 and $1,000 per month after taxes

40. Do you think you could live off Social Security benefits plus the interest generated by your savings without having to spend the principal?
(a) Yes, no problemn(b) Yes, cutting back on a lavish lifestylen(c) Yes, cutting back on everythingn (d) No way

41. If you don’t have enough, how do you plan to get the income that you need?
(a) I will rely on my children/expected inheritance to support men(b) I will sell property and possessions to raise the moneyn(c) I need to work part-timen(d) I need to work full-time

42. Can you afford the rent/mortgage where you are living?
(a) Yes. n(b) Mortgage may adjust upward, putting me in a pinchn(c) Insurance rates and taxes may adjust upward, putting me in a pinchn(d) No. I need to downsize and move immediately

43. What do you expect your retirement benefits to do?
(a) Increasen(b) Decreasen(c) Keep up with inflation onlyn(d) Stay the same

44. What do you expect your investment income to do in the next 1-3 years?
(a) Increasen(b) Decreasen(c) Keep up with inflation onlyn(d) Stay the same

45. What do you expect your investment income to do in the next 4-8 years?
(e) Increasen(f) Decreasen(g) Keep up with inflation onlyn(h) Stay the same

46. Do you have enough health insurance?
(a) Yes, as a retirement benefitn(b) Yes, that I pay for via a group that I joinedn(c) Yes, that I own individually and pay out of pocketn(d) No

47. Do you have enough prescription drug insurance?
(e) Yes, as a retirement benefitn(f) Yes, that I pay for via a group that I joinedn(g) Yes, that I own individually and pay out of pocketn(h) No

48. Do you have enough dental insurance?
(a) Yes, as a retirement benefitn(b) Yes, that I pay for via a group that I belong to/joinedn(c) Yes, that I pay out of pocketn(d) No

49. Do you have long-term health insurance?
(a) Yes, as a retirement benefitn(b) Yes, that I pay for via a group that I belong to/joinedn(c) Yes, that I pay out of pocketn(d) No

50. Are you afraid to make mistakes?
(a) Alwaysn(b) It scares me that I don’t recognize the mistakes that I make until it is too laten(c) I hate to look foolish, especially if I know better, but sometimes I get screwed by 3rd partiesn(d) I recognize the mistakes that I make and try to learn from them

51. Are you afraid to break your lifestyle pattern?
(a) No. I am fearlessn(b) Sometimes, depending how earth-shattering the break isn(c) Yes, until I get used to the idean(d) Yes, always
52. How adaptable are you?
(a) I am very creative and adapt to anything quicklyn(b) I adapt reasonably welln(c) I don’t like change at all, but I will adapt eventuallyn(d) I don’t adapt well

53. Do you think there is only one right answer to every question?
(a) Yes, minen(b) Yes, when reasoned or argued welln(c) Rarely, since everything is relativen(d) Never

IF THE FUTURE LOOKS UNCLEAR AND UNPREDICTABLE TO YOU, YOU HAVE PROBABLY DECIDED TO LOOK FOR A JOB AFTER RETIREMENT AND THINK ABOUT WHERE AND HOW YOU WANT TO LIVE. THE FOLLOWING QUESTIONS WILL HELP YOU DETERMINE HOW YOU WANT TO PROCEED.

54. How do you gather career information?
(a) Websites, listservs, online groups, company research, job adsn(b) Libraries, books, print median(c) Colleagues, friends, relativesn(d) Job fairs, job banks

55. What career information have you looked for on the Internet?
(a) Salary levelsn(b) Career and labor market informationn(c) Career planning, resumes, etc.
(d) Continued education and training, including business start-ups

56. What sources of networking do you have available to you?
(a) Professional meetings/conferencesn(b) Colleaguesn(c) Friendsn(d) Relatives

57. Do you think you could ask your friend/colleague for a referral?
(a) No. I am too embarrassedn(b) No. I wouldn’t know what to sayn(c) Yes. But it would be awkwardn(d) Yes. No problem

58. What are your options for finding a job, given your experience and skills?
(a) Excellent. I could work tomorrown(b) Goodn(c) Fair. I have few transferrable skillsn(d) Poor. I have no transferrable skills

59. Is there a market for your experience and skills?
(a) Yesn(b) Maybe, if I got additional training to become current in my fieldn(c) Non(d) I would have to research this

60. What type of organizations are appealing to you?
(a) Big corporation, like I am used ton(b) Small company, like I am used to n(c) Start-up, where they need men(d) No organization: self-employed or sub-contracting

61. What training do you think you need for improving your human relations skills?
(a) Active listening and empathyn(b) Team buildingn(c) Counseling and guidancen(d) Motivation, mentoring, coaching

62. What training do you think you need for improving your counseling skills?
(a) Teaching and tutoringn(b) Creating learning environments and materialsn(c) Illustrating concepts with examplesn(d) Advocating for others

63. What training do you think you need for improving your leadership skills?
(a) Negotiating, bargainingn(b) Strategic planningn(c) Building team loyalty and inspiring othersn(d) Making hard decisio

64. What training do you think you need for improving your management skills?
(a) Organizing, establishing procedures and organizing structuresn(b) Hiring, firing, Reviewing and evaluatingn(c) Delegating responsibilityn(d) Implementing policies with action plans

65. What training do you think you need for improving your communications skills?
(a) Public speakingn(b) Developing promotional and sales materialsn(c) Writing reports/letters/talking pointsn(d) Interfacing with the media, advertising

66. What training do you think you need for improving your creative skills?
(a) Formulating n(b) Synthesizingn(c) Program or project designn(d) Visualizing

67. What training do you think you need for improving your analytical skills?
(a) Keeping track of detailsn(b) Reasoning and abstractingn(c) Prioritizingn(d) Interpreting facts for future actio

68. What training do you think you need for improving your organizational skills?
(a) Computer training, word processing, database, graphicsn(b) Time management n(c) Budget management, billing, invoicing, taxn(d) Cost analysis

69. Do you currently have a network to tap into for career guidance/job leads?
(a) Non(b) No, but I can look up things on the webn(c) No, but I can start compiling a list of names, phone numbers and emails of people I known(d) Yes, I have already have a list

70. What type of salary do you expect to earn, if you were to find a job?
(a) Comparable to my last salaryn(b) More than my last salaryn(c) Less than my last salaryn(d) I wish to volunteer

71. What type of benefits do you expect to receive, if you were to find a job?
(a) Medical, dental, 401K, stock options, life and disability insurancen(b) Medical, 401Kn(c) Medicaln(d) None

72. How would you like to portray yourself to a potential employer?
(a) Seasoned professionaln(b) Casual professional/mentor/academicn(c) Genius with valuable insightsn(d) Energetic, eager to learn new things

73. Do you have the wardrobe/accessories appropriate for the image you wish to portray?
(a) Conservativen(b) Contemporaryn(c) Casualn(d) Unconventional

BEFORE YOU PLUNGE INTO THE JOB SEARCH, THE NEXT RULE OF THE GAME IS TO GO BACK AND LOOK AT YOUR ANSWERS. IT IS LIKELY THAT THE PRECEDING EXERCISE HELPED YOU TO RE-EVALUATE YOURSELF AND YOUR GOALS, SO TAKE THE TIME TO REVIEW WHERE YOU ARE AT.

NOW THAT YOU HAVE A BETTER UNDERSTANDING ABOUT WHO YOU ARE AND WHAT YOU WANT, GIVE THESE SAME QUESTIONS TO YOUR SIGNIFICANT OTHER, IF YOU HAVE ONE. COMPARE YOUR ANSWERS. YOU MAY WANT TO USE THIS OPPORTUNITY TO TALK TOGETHER TO BETTER DEFINE YOUR MUTUAL GOALS AND AVOID CONFLICTS BEFORE PROCEEDING.

IF YOU HAVE REACHED THE DECISION THAT YOU HAVE TO START LOOKING FOR A JOB AFTER RETIREMENT, ONE OF YOUR MAJOR CRISES IS OVER. IN ORDER TO FOCUS ON THE JOB SEARCH PROCESS, YOU HAVE TO ASK YOURSELF SEVERAL MORE QUESTIONS. THESE SHOULD TAKE SEVERAL HOURS TO ANSWER, SO TAKE THE TIME TO WRITE IN YOUR ANSWERS.

ONCE YOU ARTICULATE THESE ANSWERS, HOWEVER, YOU WILL HAVE THE BASIS FOR DEVELOPING AN UPDATED, GENERIC RESUME. YOU WIL ALSO HAVE DEVELOPED SOME OF THE TOOLS YOU NEED TO MAKE YOURSELF INTERESTING AND ATTRACTIVE TO FUTURE EMPLOYERS. YOU SHOULD RESEARCH EVERY JOB, AND REASSESSYOUR BACKGROUND TO MATCH THE SPECIFIC JOB REQUIREMENTS.

74. Are you familiar with techniques for resume building or interviewing?
75. Can you describe in ten seconds what your responsibilities were in your previous position?
76. Can you describe in two minutes what your major achievements were in your previous position?
77. Of those achievements, which would you like to highlight/talk more about?
78. What experience is relevant for the specific job you are seeking?
79. What are your relevant areas of expertise?
80. What are your relevant skills, on-the-job training, and experience?
81. What work-related training courses have you taken?
82. Did you ever receive an award/recognition for extraordinary service?
83. Which of your skills are transferrable to another position/company?
84. Did you ever solve a company problem or take charge in an emergency?
85. Were you ever in a position to create something and implement it?
86. Were you ever in a position to launch an idea and bring it to reality?
87. Were you ever a crucial team player for the success of a project?
88. Were you ever in a position to identify a need and meet it?
89. Did you ever contribute to policy development?
90. Have you ever increased sales or reduced costs in time or money?
91. Have you ever helped others to achieve their goals?
92. Have you ever improved efficiency or productivity of your work group?
93. If asked, have you suffered any failures? been passed over for promotion? had a problem with a supervisor or colleague? (These are customary interview questions, so be prepared for them.)
94. Why do you think you would be an asset to the company you are looking for a job with?
95. Since employers are scanning resumes, are you familiar with describing yourself in “key words”?
96. Do you have a list of three people who agreed to serve as a reference for you?
97. What are my transferable skills?
98. What jobs require or use those skills?
99. Where can you find those jobs?

CONGRATULATIONS! YOU WON THE GAME AND NOW HAVE SOME TOOLS TO COME OUT OF THE CRISIS OF THE TRANSITION. YOUR DECISIONS CAN BE TRANSLATED INTO ACTION. LET THE REAL GAMES BEGIN!

ONE LAST QUESTION: WHO ARE YOU GOING TO CALL FIRST?