What’s Next? Finding Goals and Ambition When You’ve Conquered Challenges

Readers of The Simple Dollar find themselves at many different points on their financial journey. Some people are just realizing for the first time that they really need to get their finances in shape. Others are in a “honeymoon” period, enjoying the discovery of frugality and of life-changing financial moves. Still others are in the midst of what I call the “long slog” – the years of consistent good choices that are needed to achieve big financial goals.

There are some, though, that find themselves at the end of that “long slog.” Their personal resilience and ambition have pushed them all the way through and they’ve achieved some big goals. They have a good job, one that they’ve worked hard to secure. They have their debts paid off. They’re saving more than enough for retirement. They have all of the things that they so desperately wanted years ago and through a ton of hard work, they’ve achieved it.

So what’s next?

Many people find themselves amazed to hear that, quite often, others who have achieved big things – big goals that they themselves hold, like a great career or financial independence or a strong family – are actually unhappy once they’ve achieved it. They have all of these wonderful things, so how can they really be unhappy?

The truth is that many people actually thrive on challenge rather than on success and when that challenge is finally complete and you stand on the summit, it’s exhilarating for a bit, but then you’re left feeling empty.

If the challenge drives you out of bed in the morning and suddenly the challenge is gone, what’s the motivation to get out there and bust your tail? It can become seriously tempting to start coasting… but for people who thrive on a challenge, coasting is boring. Plus, it also means a step back in your level of quality that you’re known for producing in all aspects of your life.

It’s a crossroads that many people find themselves at once they’ve really established a strong financial backbone in their life. The wolves aren’t at the door anymore. Everything is automated and the march to retirement – maybe even early retirement – is more or less a foregone conclusion if you just keep clocking in and clocking out. You’ve done it. You’ve achieved the “American dream.”

But what if you’re utterly bored? What if you’re completely unsatisfied at that point?

Here are some paths to think about going forward.

Envision Your Ideal Life in Ten Years

I found myself at perhaps the biggest crossroads in my life in late 2011, when I had sold The Simple Dollar to new owners and agreed to stay on as the primary writer for the site. At that point, due to our efforts financially and professionally over the last several years, Sarah and I found ourselves in the healthiest financial shape of our lives. We had worked very hard, lived very lean, and paid off our debts before selling the site, so the income was merely a cushion at that point.

For the first several months after that sale, I kind of drifted. Our goal had been to achieve debt freedom with a healthy cushion in the bank and adequate retirement savings. That had been our mountain to climb from the start of 2006 to the end of 2011 – a six year period. And we had achieved it.

The thing that turned everything around for me was the encouragement of a friend, who suggested in the spring of 2012 that I sit down and seriously think about what I wanted my life to be like in ten years. I should encourage Sarah to do the same and then merge our pictures so that we were working toward the same thing.

So, what did I want my life to be like in 2022? I wanted to be a supportive parent for my children in their teen years, because in 2022 we will have three teenagers under our roof. I wanted, ideally, to be on the precipice of retirement, something I wanted to do right after they’re moved out, and Sarah can join me if she wants in that timeframe. (Don’t worry, I have many thoughts about what to do when I no longer have to work for money.)

But more than anything, I realized I wanted to spend those ten years helping people, something that I had really come to love about The Simple Dollar.

So, what have I done since then? I’ve put the pedal to the floor when it comes to saving for the future, building up a very healthy bundle of savings. I’ve focused on a daily schedule that maximizes my effective parenting time, meaning I’m there when the kids get on the bus in the morning and I’m there to help with homework and life conversations and some fun when they get off the bus in the afternoon. I’ve become extensively involved in volunteer work in what spare time I have, including such things as phone banking for political candidates that I care about, stocking the shelves at a food pantry, and serving on the board of the umbrella organization that manages the food pantry, even serving as president of that board. That’s really what I want to be doing right now with most of my time, and I’m doing it.

So, think about the life you want to live ten years from now. Keep it within reality, but make it something that will make you reach for it. What does that life look like? What makes it incredibly desirable for you?

That’s your new motivation: building that life. For me, it meant continuing my financial progress far beyond my initial goals. It meant committing to several lifestyle changes, some of which have clicked and some of which have been a challenge. It meant taking on new professional and community challenges.

That picture of 2022 looks far more real at the four year mark than it did when I started.

Give this type of thinking some time. Think about that picture of your future right now, but then come back to it later, and come back to it again and again. Think of the wide variety of things that you might be doing in those years and ask yourself which ones are most meaningful.

What will happen is that you’re going to eventually find elements that really hit home for you. They’re going to feel deeply meaningful. They are going to excite you and they might give you a “punched in the gut” feeling. Those are the ones that you need to focus on because those are the ones that are truly close to the core of who you are. Those are the key pieces of your life for the next ten years (or so).

Accelerate Retirement

One aspect that many people will find in their visions of an ideal future is that they’re retired, or at least in a state where they’re spending most of their time on things that aren’t necessarily geared toward earning money.

To do that, of course, you’re going to need a lot of money in the bank to cover your living expenses, which means that saving for the future is going to continue being a major thread in your life.

There’s no real need to change how you do it, just that you continue to do it with ferocity. The purpose of a vision of the future without work is the motivation for that fury. It’s no longer about escaping a financially insecure position. It’s about building an amazing, meaningful future.

Even if early retirement isn’t part of that vision, it’s likely that your vision for the future includes something that requires significant capital to pull off, like owning a small business without being in thrall to a bank. That can also provide the motivation you need to keep making financial progress.

Be Intentional with Work Projects

For many people, having a reputation as someone who produces quality work is extremely important. Many, many people want to be known as the person who gets things done or who is always involved with successful projects.

At the same time, many people find themselves working on professional projects that they don’t particularly value. The outcome of this project does not feel important to them, so it’s hard to be focused or involved or motivated. Being a high achiever is hard to do when you’re working on something that is meaningless to you.

Here’s where you can take your solid financial foundation and put it to work. Because you’re not standing on the precipice of financial doom, you have a bit of leverage at work that you didn’t have before. Use that leverage. Make it so that you’re involved with a project in your workplace or a role in your workplace that is meaningful or exciting or interesting to you. If there isn’t one, look for another employer.

It’s worth remembering that in any big project, not every task is going to be fun, but if you are working on a project you believe in, every task is meaningful. In the times in my life when I’ve worked on a project that I really believed in, I didn’t mind doing the less-fun tasks that needed to be done to make the project successful. It was only when I no longer believed in the project that the less-fun projects became misery.

Be intentional at work. Make sure that you’re working on things that are meaningful for you, whether it’s due to intellectual interest or because of the impact of whatever it is that you’re producing. Use your relative financial freedom to move yourself onto a project that lights a fire under you.

Develop a Side Gig with Meaning

Perhaps you find yourself in a job that’s comfortable, that pays well but isn’t particularly challenging, and you don’t want to rock the boat as it sails on toward retirement. Many people find themselves in this position, where they have a skill set that practically guarantees them a good job but it’s one that isn’t particularly challenging most of the time.

In those situations, it’s probably a poor long-term decision to rock the boat at work, but you need something to channel your energy and ambition. In those situations, a side gig can be perfect.

There are many, many kinds of small side businesses you can launch on your own. The internet offers nearly infinite opportunity for people with ambition and patience – you can start a Youtube channel or a blog or start writing books for the Kindle store or selling your crafts on Etsy or even stream your video game play on Twitch or writing a smartphone app. In the offline world, the options are just as infinite, from launching a lawn care business or seeking freelancing work or simply making things in your garage for sale (like the guy who lives near me who sells wooden chairs he makes in his garage).

The key here isn’t just to launch something that seems like it will make money, but to launch something that is meaningful to you. You want to choose something where it will be joyful for you to sink a lot of hours into the project, discarding some of your other leisure interests in order to devote time to this project.

The Simple Dollar is a perfect example of this. I launched it as a side gig in 2006. By mid-2008, it had grown so large that it basically forced itself into becoming my full time gig. By 2011, it was so large I had to have multiple assistants to keep the ship running. Why did that growth happen? The work was meaningful for me. Every time I got an email or a message from a reader telling me that something I had written had helped improve their life, I felt good in a way that my previous job never really gave me. It’s that meaning that keeps me writing tens of thousands of words per week for the site.

When you find something that’s meaningful and something that really engages your skills, you’re going to find something powerful that you really want to sink tons of time and energy into.

Get Involved in a Social Project

On the other hand, you may find that the things that are most meaningful for you aren’t things that lead to profit, but instead things that lead to positive social change.

Perhaps positive social change for you means building houses every weekend with Habitat for Humanity. Perhaps it means getting involved in politics at the local level, or getting involved with campaign work at the state or national level to produce the kind of candidates you want to see for our state and national leadership. Perhaps it’s building up a local food pantry. Perhaps it’s writing open source software that anyone can use.

It comes down to finding a project that’s meaningful to you, either in the execution of it or the outcome of it. Either you find the work deeply personally engaging or you have a deep desire to see the outcome in the world that’s produced by that project.

Handling the Risk Question

Here’s the catch: most of these suggestions do involve some risk with the life you have right now. That risk might come in the form of pushing for changes in your workplace role, or it might come in the form of putting the focus of your energy on a project outside of your primary workplace.

For someone who has spent many years on a financial and professional journey building up job security at a well-paying job and building a level of financial independence for themselves, introducing that kind of risk can seem pretty scary.

Here are some points of advice for considering risking what you have for something more.

First, you’re probably not reading this if you’re thoroughly happy with your current life situation. It’s probably because there’s no challenge in your life. Part of the path to introducing challenge in your life is to introduce some risk. Without something at risk, without something on the line, there isn’t a whole lot of challenge.

Second, you should look at your job as “the thing you do to provide the income needed to do what you care most about.” Recast your job not as drudgery to maintain your life, but as a key part in whatever thing you’re taking on that you truly care about. You work at your job so that you can afford to spend hours working on Habitat houses or building that side business of selling jewelry on Etsy or whatever it may be. Your job is a key part in that; every task you complete at work is a task that helps your personal passion projects.

Third, you likely have a great deal of economic security. If you’re feeling like you’ve achieved your economic and professional goals, it’s likely that you already have a significant net worth. You should have your debts paid off and some money in the bank. If you don’t have that, then that should be your major goal.

However, assuming you do have those things, it’s important to remember that even if you do put your current job at risk, it’s not the end of the world if that risk doesn’t pay off. You’ve worked to give yourself the freedom to take a little bit of risk in your career; otherwise, what really was the point of doing it?

Finally, meaningful work can change your life. It can often change your life in unexpected ways. I view the writing that I do for The Simple Dollar to be meaningful work and through that work I have had many many wonderful things happen in my life that I never expected, from building relationships with people in the town where I live to understanding myself and the world in completely new ways. I took on some career risk when I started The Simple Dollar; that risk was worth it, and would have been worth it even if The Simple Dollar never earned a dime for me. It changed my life in ways that I never, ever expected because of the relationships it built, the ideas it made me discover and understand, and the elements of character it drug out of me.

Whenever you take on a new challenge that’s meaningful for you, those things are going to happen. You’re going to discover new things about yourself. You’re going to build new relationships. You’re going to learn new ideas and skills. Even if the economic risk doesn’t pay off, those things will remain and they are elements of almost anyone’s definition of a better life.

Final Thoughts

If you’re the type of person who has enough grit to build a strong career and a strong financial foundation for you and your family, you’re going to be gearing up for a new challenge once you have achieved those things. Listen to your heart now. Ask yourself where you’d really like to be in ten years and give that question some truly serious thought. You’ll know when you find the right answer, because it will just ring true for you, and then you have the basis for your next challenge.

The best part? You’ll realize that the mountain you’ve already climbed – the building of your strong financial situation and your great career – is just the foundation for the next challenge.

Good luck!

The post What’s Next? Finding Goals and Ambition When You’ve Conquered Challenges appeared first on The Simple Dollar.