Know When to Start–and When to Quit, Too

Long time, no see, readers!

I’ve had a few crazy months since my last blog post. I have a laundry list of blog topics, but I’ve been prioritizing podcasts, seminars, and clients as I figure out the best way to disseminate information across a variety of social media platforms. I love the immediacy of Instagram, but sometimes it’s nice to sit down and write you a letter to let you know what’s really on my mind.

This might be something of a hodgepodge because there are so many things I want to address, but I’ll try to keep it short and sweet.

This is about how to figure out whether you should start something: A diet. A workout routine. A new career.

It’s also about how to figure out whether you should quit something: A diet. A workout routine. An old career.

Well, yea…easier said than done.

It may come as a surprise to you that I advocate quitting. Society tells us that quitters never win, winners never quit, and quitters never prosper. This is all nonsense. Successful people aren’t immediately successful at the first thing they ever try. It’s prudent to quit things; it saves time and energy that we could be spending on more fulfilling and potentially successful endeavors. The trick is to know when to quit. It’s just as important to know when to start, too.

There’s arguably no perfect time to start something new, especially if it’s a serious undertaking. If you’re really mulling it over, chances are there’s risk involved, so your trepidation is warranted. Modifying your diet and adopting a workout routine both require time, energy, planning, and some level of sacrifice on the part of your old habits. Starting a new career–whether you’re fresh on the market or leaving a previous employer–carries significant financial, professional, and personal risk. Likewise, there may not be an ideal time to quit something, and you’re probably going to face some cognitive dissonance as you grapple with the question of whether quitting is the same as giving up, or if quitting this thing makes you A Quitter (whatever that means, honestly).

I’ll preface the rest of this by saying that I’m no professional life coach, so what follows is a combination of my interpretation of some very helpful books along with my own experience quitting.

I’ve quit a number of things:

  1. My original college major
  2. My original college boyfriend
  3. Some sports, including distance running and basketball (I’m 5’0)
  4. Every retail job I’ve ever had
  5. Also my actual academic career


Yes, I resigned. After four years as an assistant professor, I left academia. I don’t know if I’ll stay out of it forever, but for now, I don’t intend to return. It was not a decision that I made lightly, or without a great deal of preparation. I quit that to start something new, but I couldn’t start that new thing without a safety net and a plan for success. I only quit once I realized that I was no longer progressing in ways that were meaningful to me. I quit something that was actually going to be easier in order to do something more challenging and even a little frightening. This is where most people go wrong: They quit the challenging thing to do what’s easier, even though they lose out on all of the potential success that way.

In “The Dip,” Seth Godin describes a scenario that many people have faced, whether personally or professionally. It’s the Cul de Sac. It’s The Song That Never Ends, from Lamb Chop’s Sing-A-Long (for you 90’s kids). It may look like yo-yo dieting when you keep losing and gaining the same 10 pounds, or months hitting the gym with the same routine and no results, or years in a job that provides only lateral movement. It may feel safe because it’s familiar, and the thought of turning down the street rather than making another loop is just too overwhelming, but it’s an insidious parasite. You’re spending time there, but you aren’t utilizing your time productively. You don’t get it back once it’s gone. This is the thing you want to quit.

Welcome to purgatory!

The Dip, on the other hand, is a different type of grind. The Dip doesn’t feel safe. It feels tough, and tiring, and frightening, and challenging. It’s tiring in a very different way, like the fatigue you feel after you’ve done something physical and productive. The fatigue of the Cul de Sac is the same ennui you feel after sitting for too long. People tend to quit in The Dip rather than the Cul de Sac, because The Dip exists so near failure. This is not the thing you want to quit. This is the thing you want to dig into.

The Dip is only a temporary delay in the returns on your investment.

Any new endeavor will come with The Dip. After the excitement has worn off, you realize that there’s still work to be done. You haven’t freed yourself from labor, but you’ve given yourself the freedom to labor for something that nourishes you. A well-designed weight loss diet will leave you feeling hungry. A challenging workout routine will leave you feeling sore. A new career will likely demand more of your time and energy, and if you take the leap toward total entrepreneurship, it’ll demand your money, as well. There’s a chance that your new endeavor can become a Cul de Sac, though, and you’ll be expending these precious resources to continue moving in circles. Be sure to stop sometimes and take a look around: Are you still in exactly the same place as you were weeks or months ago? Can you see any internal or external changes? Slow progress is still progress, but it’s important to discriminate between the discomfort of growth and the pain of repetitive overuse. Before you start, set benchmarks of success as well as pit stops to look out for red flags.

Starting something at the right time will increase your chances of success. Remember, there’s no perfect time, but there are better times.

Thinking of starting a diet to lose weight? What social events do you have coming up? What are your current culinary skills? What time commitment can you make? Can you afford to feel tired and hungry in the next couple of months? Be realistic. Is your life at this point conducive to sticking to a diet? If not, what’s a better alternative? Prevention of weight gain? A shift to healthier habits? Set realistic goals at the right time.

Thinking of starting a workout routine? What’s your exercise history? Are you looking into plans at the appropriate level for your experience? Are you looking at plans at all? Any movement is better than no movement, but going in without any structure at all will not lead to success. It doesn’t have to be an extravagant program, and you don’t need to spend hours in the gym, but the best way to measure success is by improvements in your movements.

So…thinking of starting a new career? Obviously, that’s a far more serious consideration. I can only tell you what I did: I worked nearly every day for a year, and saved all of the money I earned from my ‘side hustle’ as well as anything else that I could. I spent very little on extraneous expenses like clothing, restaurant food, or travel. I enjoyed the lovely free things in life, like long walks outside. I read about entrepreneurship and pathways to additional credentials that would help me serve my clients. I spent money on those credentials because I viewed them as investments. I learned new skills and marketed myself in different ways, even though they were far out of my comfort zone. I’ll be the first to tell you that I’m not an eloquent speaker, but I am honored to be invited to speak on podcasts and to give seminars. I say yes as often as I can. I also learned more about myself and my needs as an introvert entrepreneur, because when it comes to taking a leap like this, you have to know when to apply your own oxygen mask. I also networked with like-minded individuals and opened myself up to friendships and connections with people who had sincere faith in my abilities, even when I experienced doubt. When I provided my formal resignation, I did it with care and professionalism. I didn’t make that final decision until my finances and plans were in order–and by that, I mean that I could support myself for quite a while even if things went awry. I knew that I had the knowledge, skills, support, and finances for the best chances of the success. The timing was right to leave the Cul de Sac and face a Dip.

In short: Before you start something, know that you have the internal and external resources to see it through or bail yourself out. Know the stakes, and also know when you’ll quit. Make a plan for success and a plan for the alternative–which doesn’t necessarily have to be failure. I didn’t fail at my career. I chose an alternative that I knew would foster growth, development, and fulfillment, because of the challenges I’d face. 

Having read Godin’s book, I now expect The Dip to hit at any moment. Perhaps I’m in it now, and I just haven’t realized it yet. I enjoy the flexibility of making my own hours and I love my work, so I don’t notice how many I actually dedicate to it, but I know that I don’t take days off. There’s really no such thing as free time now that I have long-term projects like writing a book, preparing for seminars, and completing coursework toward becoming a Registered Dietitian. The past four years have flown by, and I can only imagine what the next four might have in store. That’s the thing with Cul de Sacs and Dips: the time passes in either place, but only one provides a change of scenery.

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