Time for Your Second Act? 6 Keys to a Successful Move

I’ve recently had the opportunity to enjoy “next step” discussions with some very experienced business leaders: start-up execs, business owners, and long time employees.  The common threads?  They’ve all been folks with 20-30 years of work experience, moderate to major professional success, are now in shifting situations and are looking for their “second act”.  I suppose you could call this “middle age” from a professional perspective but it is something much more than age.

In a world with the notion of retirement shifting before our very eyes and potential lifespans that make long range planning very difficult, the concept of a second act has become critically important for a myriad of personal and professional reasons.  We are faced with a long run (if we’re lucky!), we are evolving along the way, the rules are radically different from when we started, and things continue to change as we progress.  Very challenging.

Though the challenges exist at every stage of your journey, there is a keen edge for mid-life professionals with a sense of time passing, major commitments still pressing, and a potentially long road still ahead.

There is a certain gravity to this phase of life.  A central pull resistant to change even while we feel called to change.  In many ways, we are expected to have already “arrived”, a point at which we are enjoying our peak professional powers, peak earnings, and peak stability.

Alas, this is not always the reality as we support adult children or aging parents, pay-off educational loans, or face the persistent instability of corporate staffing shifts over which we have no control.  It isn’t easy.

Take heart!  In the face of these transitions, there are tremendous opportunities and I can’t help but convey optimism to anyone with whom I speak.  Here are some key points from some of these recent discussions:

  1. Ignore the Statistics – OK, maybe ignore is the wrong word.  You should always be educated on the realities and be aware of the challenges.  However, statistics and pundits tend to paint trends in broad strokes that are good for articles and newscasts but not particularly relevant to the individual.  Your skills, experience, geography, attitude, and timing are unique to you.  Don’t get caught up in national doom and gloom stats that may or may not apply to your situation.  The same applies for “the next big thing.”  Your next big thing will most likely NOT be on another person’s list.
  2. Think Broadly – One challenge I often see when talking to people considering transition is that they tend to focus in two areas: 1) jobs/careers that are very similar to what they are currently in or 2) jobs/careers that are WAY outside of anything they’ve ever done – complete restarts.   Keep those two categories on your radar but remember that there are many, many things in between.  Common options that I like to mention are: buy/start your own business, not-for-profit work, industry transitions, hybrid roles, or geography shifts (looking outside of your backyard – all of which leverage solid experience that you’ve already built.  My point is to think of how you reapply what you’ve done, not necessarily “start over.”  (Though it may feel like you are starting over).
  3. Engage Your Network Appropriately – Reaching out to friends, family, and business associates is an absolute must.  However, getting the most from these conversations requires planning.  You should have an inner circle with whom you brainstorm.  A second group with whom you are familiar that may have some good ideas and then a third, broad group that you approach with specific requests for support.
    • Inner Circle – they know you well and will give you honest feedback on your strengths and weaknesses.  However, remember that this group also sees in you in a certain light.  They may not be the best to help you think creatively about your capabilities.
    • Acquaintances –  this group comprises acquaintances with whom you are familiar but are not intimate.  You should not approach this group looking for emotional support, but use them as idea generators or connections to other people.  The odds are, your best connection to a direct opportunity will not come from your own network but from someone to whom your network connects you.
    • Helpers – these are people to whom you make direct requests.  They are generally referrals from Acquaintances and will have an interest in helping, to a point.  When you get to this round of folks, you should be requesting something specific: an introduction, piece of information, or an opportunity to apply.  Don’t approach Helpers looking for advice on your situation: they don’t know you or your situation.  Approach them with your plan and with an idea of how they might help you.
  4. Maintain Buy-In At Home – If you are in a relationship, buy-in from home is a critical factor.  However, remember that your partner will likely want you to take the safest path.  This isn’t because he/she doesn’t love you and want the best for you.  It is out of fear of the unknown, the fact that he/she is not in control, and his/her own experience.  This key person in your life wants you to be happy and successful, but will naturally lean toward the path of the known.  You will need to sell your hopes, dreams, and PLANS to this person.  Don’t be frustrated or discouraged by this process.  If you can’t make a case that convinces them, perhaps your hope or dream isn’t the right one at this time.
  5. Financial Planning – I tend to steer clear of the financial aspect of this process because there are so many nuances and it only gets more complicated as we get older.  The major point here is to thoroughly understand your situation, opportunity, and tolerance for risk.  You’ve got to be very realistic.  As we get older, the stakes are higher because we have less time to recover from failure.  Find a place with which you (and your significant other) are mostly comfortable.  This is one reason why I often encourage would-be entrepreneurs to look at existing businesses to buy.  This can help mitigate the risk of entrepreneurship while allowing you to pursue a dream.  Jobs that require pay cuts, are more highly leveraged toward success, and/or are with higher risk organizations all sit at some point on your financial risk continuum.  Be mindful but don’t let fear drive your decision.  Fear can kill any dream before it has a chance to come to fruition.
  6. Be Patient – Even if you have to jump into something less-than-ideal to generate income, be patient.  This second act likely won’t be your last.  If you don’t pivot to the ideal next step, then keep looking until you do.  Remember that the best situations are built: you start somewhere and then make it what you want it to be.  This applies as much when you’re 50 as it does when you’re 22.

Ultimately, you have to trust yourself and follow your instincts.  Our situations vary so widely and are so unique to us that no one plan fits all.  I challenge you to keep your heart and mind open to all possibilities and hold on to faith in the possible; a belief that things will work out.  No, it will most likely not match your plan but it will work out.

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