What To Do When You Succeed (and Fall Off the Wagon)


This post is provided by Will Haines of www.itcanbeeasilydone.com. Will is a blogger, an entrepreneur, product expert, investor, and lover of all things effective. Over the past decade, he's created a bunch of high-use products, led teams in a variety of technical fields, and launched a successful crowdfunding platform. In his personal and professional life, he's been super-focused on learning the most effective ways to achieve his goals faster and with less stress.

Success Is Sweet?

Congratulations! You did it. You saved up enough to buy the car in cash. You lost 15 pounds. You finally finished the marathon. You saved up enough to retire right now (or maybe not). Big or small, achieving a goal you set for yourself feels great. Give yourself a pat on the back and onto the next thing. Right?

It’s often not so easy. What comes next after you achieve a big goal? Without the right mindset and support structure, even Olympic gold medalists can fall off the wagon. While your big achievement might not send you spiraling into depression, it might just kill your momentum.

Today let’s get you set up so that your successes build on one another instead of crashing and burning.

Planning for Success

Step 1 is recognizing the problem. You probably have a plan for making progress against your financial goals, and you probably put this plan together at the height of your enthusiasm. Just thinking about being able to buy a house or not having to budget quite so tightly is enough to get you going.

After a big success, recognize that you probably won’t be enthusiastic. You’ll be tired. That was hard work after all! As such, you’ll want to make your plan now when you do have the energy. I recommend thinking about ways to sustain your success and do so more efficiently.

For example, did you lose 50 pounds by running every day? You probably don’t need to do that for the rest of your life, but if you want to keep the weight off, you’ll need an easier weekly exercise plan that you can imagine doing for years. Or on the money side, maybe you saved up the cash for the car by cutting out restaurants. Now that you’ve succeeded, is there a way to keep something like that going? How about taking a quarter as much as you’ve been saving out of your paycheck upfront and putting it into a fund to make sure you always have money to cover maintenance? Automation—now that’s a plan you can stick to.

It’s the Cycle of Life

It’s great to have a plan, but you also need to recognize that human beings aren’t built to go at 100% all the time. Pushing yourself too hard for too long can lead to burnout, which will really prevent you from making progress. The end of a long goal is a natural place to take a breather.

The trick is to make sure that you are able to come back strong after breaking your routine. One way is to back off but make sure you don’t break the chain. That is, do less but still be sure to do something every day. If you’ve been putting 2 hours every morning into your side hustle, spend a week getting up later and just checking one item off your todo list. Or if you’re learning a language, just review one word each day. You still have accountability, but you spend much less time.

Once you’ve cycled down, you’ll need to cycle back up into doing things that take more effort. Here, the best approach is to start with the smallest possible thing, then build up steadily. Powerlifters don’t bench press a personal record every workout. They build up to it. You can do the same. Now that you have a 6-month emergency fund, you might want to build up your IRA. Start this month by putting in $50, then gradually raise the amount until you start to see a real change.

Zoom Out: Are You Really Done?

Now you have a plan to sustain your success and you know how to back off without falling off. However, you may be wondering what your next goal should even be. I’ve written extensively about how to define and achieve any goal, but in this case, you’ve already had some success. Let’s leverage that and zoom out by using the five whys.

Ask yourself why you picked this goal in the first place. “I saved this money so that I could buy a new car.” Now ask yourself why that is important to you. “I want a new car because I need a reliable car.” And again for a total of 5 whys, getting down to: “I want to turn my money into more freedom.”

Note that this root cause is much broader than figuring out ways to save money on the car. If you want more freedom, maybe your next goal should be to find other ways to trade money for time (e.g. hire a house cleaner) or to find ways to stop trading time for money. That could be a lifetime of goals right there.

That said, maybe you really should just stop. If you dig in on your goal and realize that it is a one-off or that you’ve really accomplished everything you want, there is no shame in quitting. Find something else you want to do. It’s your life.

From High-Fives to Habits

Let’s wrap up by talking about the difference between goals and systems. As you advance it is possible to sidestep the whole problem of bouncing from goal to goal and sometimes falling off the wagon by focusing on building out processes that contribute to your ultimate success.

Goals, even big ones, tend to be specific and fairly short-term. That’s great, but if you’ve just succeeded at something big, I suggest that you take a step back and try to extract some broader lessons that you can apply every day. Did your savings goal teach you something about paying yourself first or about what items you can easily cut vs. which are more painful? Did your diet teach you anything about healthy foods that you actually love? Don’t lose those insights!

In fact, I recommend taking some time every week to reflect on how things are going, what you’ve learned, and how you want to adjust. I personally use a website called Complice to do this, but you could just as easily use a journal or notebook. The key is to think critically about what does and doesn’t work for you and apply it back to your life.


Achieving your goals can be a double-edged sword. Don’t let a big achievement force you to take your eyes off the ultimate prize! With some planning, judicious breaks, and a little systematic self-reflection you can turn your successes molehills into success mountains. Have you had a recent success? How are things going now? Let us know in the comments.

Thank you to Will Haines for providing this insightful post on success and what happens when you make it. It gives us much to strive for, and we look forward to hearing more from you in the future. 


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