If Not Now, When?

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A few years ago, a close friend of mine was struggling with his job.  He worked in a large corporation he couldn’t stand:  unethical business practices, employee backstabbing, and sexual harassment all seemed to occur on a regular basis.  He wanted out.  Not only that, for years he’d harbored a secret dream of starting his own business.  Driven by his growing disgust with his company’s culture, he made a determination to do just that.

Every Monday on his way into work he’d daydream about leaving.  But by the time he’d reach his office he’d have concluded that the time wasn’t right.  He had six more months left to pay off a car loan and was planning to get married in nine.  He was well aware of the lean period that most new businesses endure at their start and was worried he wouldn’t be able to weather it.  And what if his new business failed?  Or succeeded, but not at the level he found satisfying or that could sustain his life (and his soon-to-be family’s)?  Wouldn’t it be better to save up a little more money, he asked me one day, to create a bigger buffer for the lean period he knew would be coming, and then make the leap?

“No,” I told him flatly.

Sure, I agreed, having that extra cash would be helpful—but how certain was he that he would need it?

He shrugged uncertainly.

I told him I thought his idea about needing to save more money before leaving was just an excuse to stay where he was.  Yes, leaving his current job and starting a new business represented a risk, a risk he could perhaps ameliorate a little with more money.  But could he eliminate the risk entirely?

“No,” he admitted.

The future is mostly unpredictable, I argued.  We may think we know how things will go, but things rarely turn out exactly as we predict (and often not even close).  He could save up that extra money, buying a feeling of confidence in his choice to leave, and then have a car accident that required him to pour all his extra savings into repairs and medical bills.  Or, I suggested, his fiance, who had a job she loved, could get a promotion and a pay raise and instantly make that extra money he saved irrelevant.

There’s almost never a perfect time to do anything, I told him.  Not to leave a job and start a new business, not to get married, not to have a baby.  If you wait for the right moment to appear, no moment will ever appear to be right.  We do all those things because we want to do them; we do them in spite of all the obstacles and reasons not to.  And when we don’t do them, the reasons we give are mostly designed to disguise the truth that we’re either genuinely ambivalent about doing them or we’re afraid.

This isn’t to say that careful forethought and planning aren’t important.  I’m not arguing here for waking up one day, walking into work, announcing you’re leaving, and waking up the next day without a plan about what to do next.  But my friend had his plan—a thoroughly researched, executable plan.  One that had risks (because the future isn’t completely predictable), but one he thought he could pull off.  One he wanted to pull off.  He’d rationalized his hesitation by telling himself that certain obstacles needed to be removed before he could quit.

“But once those obstacles are gone,” I argued, “other ones will appear to take their place.”  No glowing sign will ever descend from the heavens with an arrow pointing at a day your life will become easy enough to make it the right day to leap.

He agreed with me, he said.  He was ready.  He would do it.

When I caught up with him again a week later, however, he still hadn’t announced he was quitting.

“This is harder than I thought,” he said.

“Thursday,” I replied.

His expression became panic-stricken.  “What…?”

“You’re quitting on Thursday.”

“Are you sure?” he asked.

What I told him was that I was sure he wanted to quit, that he had just as much chance of succeeding as one could have, and that if he never did it, he’d regret not trying for the rest of his life.  I was a close enough friend that I felt not only comfortable but obligated to provide the slight push he needed.  “I believe you’ll be happy if you do this.  Even if, in the end, you fail.”

Sure enough, that Thursday, shaking, sweating, scared out of his mind, he told his boss he was leaving.  When his boss tried to convince him to stay, good-naturedly warning him about the likelihood of failure, a curious thing happened:  his resolve to leave and try his plan hardened like quick-drying cement.

“I’m still scared out of my mind,” he confessed later, “but I’m so happy.”

Within a year, he’d built a small, moderately successful company.  It took him even longer than he’d estimated to start turning a profit, and it ended up being far harder than he’d ever imagined.  It took him two years instead of six months to pay off his car loan, and his wedding ended up being quite a bit smaller than his fiance had originally envisioned.  But she didn’t mind.  “She likes how excited I am to go to work every morning,” he told me.

In the end, he realized he’d been asking himself the wrong question all along. If not now, when? He shook his head.  “That wasn’t the issue at all,” he said.

“What was the issue?” I asked him.

If not me, who?” he replied.

Next Week: Stupid Fights

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  • […] This post was mentioned on Twitter by Maureen Anderson, Alex Lickerman. Alex Lickerman said: What are you waiting for? https://bit.ly/fXsiNT […]

  • Thanks Alex for this post!

    This is a common situation that can be extrapolated to many different scenarios in life.

    In my situation, I was reluctant to move on because I was too scared of change, too scared in case things didn’t work out. The fear of failure totally paralyzed me into not seeking new things in life. It always helps to have someone around to give that final push. Once you DO actually make that change in your life, you are more confident about doing things to make you happy.

    Thanks for the article! Looking forward to next week’s!

  • Thanks, Alex. That was a wonderful story. Another one, very similar, but the opposite approach, is that of an extremely elderly woman, successful in many aspects of her life. She became progressively ill, and her complaint was, “Why me? Why now?” Perhaps you wouldn’t mind commenting. Thanks.

    Jay: I think the question “Why me” and “If not me, who?” aren’t opposites at all, as they may appear at first glance. “If not me, who?” has more to do with having the confidence to achieve our goals. “Why me?” has to do with denial: denial that anything bad could ever happen to us. We almost all have that denial built into us to help us navigate calmly through a world in which bad things might happen to us at any moment (and, of course, eventually do), and as such, it’s extremely adaptive. But if that denial goes too far, if we forget, when bad things do happen to us, that they can, continuing to cling to the delusion that we are in some way exempt from the pain loss—we often get stuck in a place of resentment and learned helplessness that is most definitely maladaptive.


  • I think if we can get burrow through the self-doubt and second-guessing and realize with our gut feeling on issues like this the answer is usually evident. I agonized over retiring last year and ultimately made what I now know was the right choice. (Hence my ability to both read and respond to your post this morning!)

    In the case you cited I would be wary to give the advice that clearly pushed your friend to make the decision. Now THAT’S gutsy!

    Patricia: Not as gutsy as it may seem in this case. I happened to be exceptionally close to this particular friend. Wouldn’t have done it with most others.


  • Thank you for this post. It is something I think I need to bookmark so I can return to it over and over again. I’m much like your friend … waiting for the “right time.” 🙂

  • Will Shakespeare had something to say about this, as well. He said, “Readiness is all.”

    Seems to me that those who are not-ready in a continuous way are indulging in procrastination. You suggest, Alex, that if your close friend didn’t make his move, he would look back and regret it. I see that as encouraging your friend to take the long view . . . which will always be a valiant defense against the inclination to procrastinate.

    I think it was also important to say that even if your friend’s business failed, it was still worth doing. What one learns from “failure” is so under-rated!

    The last assertion, If Not Me, Then Who?, is the subject of (many) tomes! Taking personal responsibility, saying to oneself and to everyone else, “The buck stops HERE!” is such a robust approach to all of life! I wish our political system would adopt this as its mantra, emblazoned on the walls of the halls of Congress, and over the door of every courthouse; and on the letterhead of all the branches of state and federal government.

    Three cheers for the I-Can-Do-It approach!

  • A wonderful and timely message that, in these extremely difficult economic times, leaves us fearful and paralyzed.

  • The story sounds VERY familiar. Your friend is lucky to have you as his/her friend to help “push” him/her into taking the action.

    Rhea: My friend is INCREDIBLY lucky to have me, don’t you think?


  • Hi Alex,

    We all at some point need a nudge, a shove, or simply some words of encouragement to act on our heart’s desire. It appears because you knew your friend well enough you gave him the right type of push he required to move forward on his business (ad)venture.

    When I have a conversation where someone needs that “push” I usually start by asking, “What is the worst that can happen?” They undoubtedly would reply, “I could fail miserably!” Then I would come back with, “What is the best thing that can happen?” Of course they would answer, “I’d succeed!” I don’t respond right away. We would be silent for what might seem like a long time. Finally, I would say, we can’t control what is going to happen; all we can do is release our attachment to the outcome and trust that our resolution is the right one.

    Everyday we take a leap of faith that our day is going to unfold as we expect. We believe that we know what the outcome will be but we really don’t. We can’t let fear of the unknown control our present. Do your research, prepare a plan of action with timelines, and then take action towards your dream.

  • Hmmm… this is not only about major decisions. It somehow also reflects the day-to-day decisions that we make when it comes to facing our fears.

    For example, I have been wanting to do some audio recordings for my website but I have been procrastinating. Haha, I seem to be able to convince myself that now is not the right time, and that in the future, I will be more ready.

    Which in fact it is because of my fear of how others judge my voice and audio clips.

    Perhaps the best way to deal with this is… still, do it now.

  • Alex,

    Here I was, working so hard on letting things “be” and trusting that the next step can’t help but show itself eventually. Now you make a great case for jumping ahead now! What’s a girl to do??

    I’m at a similar decision point—laid off from a job I really disliked going to, swearing I won’t be sucked into another corporate situation that isn’t better suited, hoping a possibility I hadn’t considered will pop up. Suddenly, freelance work is falling into my lap, so maybe this is that new opportunity and I should jump in with both feet. I wasn’t what I’d envisioned, but maybe it’s what I need.

    I’d be remiss to sign off without letting you know I think you are a treasure and always a joy to read.


    Lisa: Thank you for such kind words.


  • Interesting light reading on the same subject: “The Sharper the Knife, the Less You Cry”…story of a job lost and an attempt at a heart’s desire.

  • Check out the song “If Not Now” by John Gorka…


    Here’s the lyrics:
    If not us, not them
    If not now, then when?
    If not here, nor there
    If not this world
    Then where?

    If not us, not them
    If not now, then when?
    If not here, nor there
    If not this world
    Then where?

    If not us, not them
    If not now, then when?
    If not here, nor there
    If not this world
    Then where?