Get in the Right Mindset

In her book Mindset, Stanford University psychologist Dr. Carol Dweck explains that the way you view yourself can impact how you live your life – from the goals you set and the decisions you make to whether you can achieve what's important to you.¹

Dweck's decades of research found that people think about their abilities with either a fixed or growth mindset. Those with fixed mindsets believe their skills, intelligence, and talents are set in stone. People with growth mindsets, on the other hand, believe they can build on and improve these characteristics. Dweck also found that people's mindsets can vary by activity. For example, someone could have a fixed mindset when it comes to math, but a growth mindset for sports.

Dweck says that people are most likely to succeed at a task with a growth mindset because they're apt to focus on growing and learning, rather than trying to prove themselves repeatedly. As she puts it, “The passion for stretching yourself and sticking to it, even (or especially) when it's not going well, is the hallmark of the growth mindset. This is the mindset that allows people to thrive during some of the most challenging times in their lives.”

When I was younger, failing to achieve a goal would often damage my confidence and self-esteem – textbook signs of a fixed mindset. It wasn't until I lost my job in my late 20s that I began shifting toward a growth mindset. After stumbling upon Dweck's research, I realized that I had been thinking about my layoff as an absolutely terrible outcome, rather than seeing it as a learning opportunity that would help me eventually reach my goal of greater career satisfaction.

This simple discovery marked a turning point for me. With a growth mindset, I figured out that I could still apply and build on the analytical skills I had honed in investment banking, but within a different industry that better matched my desired lifestyle. Fortunately, I was able to find that combo when I began my new job at Google. My experience encouraged me to adopt an approach that has continued to keep me motivated when I face setbacks in life – including when it comes to optimizing my career and finances.

Diversify Your Identity

Another strategy for overcoming the fear of failure is diversification (read: not putting all your eggs in one basket) – a concept we touched upon earlier in relation to your career and investment strategies. But you can also diversify your very identity by taking purposeful steps to avoid defining your sense of self based on a single aspect of your life, such as your job title or the size of your checking account. In other words, diversifying your identity means valuing yourself for all the characteristics that make you you.

Tim Ferriss, technology investor and author of The 4-Hour Workweek, espouses the benefits to be gained from a diversified identity. In one of his on-screen interviews, he explained, “When you have money, it's always smart to diversify your investments. That way if one of them goes south, you don't lose everything. It's also smart to diversify your identity, to invest your self-esteem and what you care about into a variety of different areas – business, social life, relationships, philanthropy, athletics – so that when one goes south, you're not completely screwed over and emotionally wrecked.”²

I can relate to the picture that Ferriss paints. My mood was almost entirely dictated by how my job was going when I worked in finance. Sure, when I had a good day at work, I felt on top of the world, but if I happened to have a bad day, I'd quickly fall into a downward spiral. In more recent years, however, I've diversified my identity by starting a side hustle and prioritizing my family relationships. As a result, I've been able to avoid extreme emotional swings while becoming increasingly confident in my decisions across all facets of my life.

You, too, may find that a diversified identity helps you tune out messages of self-doubt that threaten to stand in the way of achieving your career and financial goals. And besides, it'll almost certainly make you happier – and who doesn't want that?

Don't Take Yourself Too Seriously

In the movie Van Wilder, the main character (played by Ryan Reynolds) provides the following advice to an incoming freshman student: “But you know what I've learned in my seven years at Coolidge … Timmy? I've learned that you can't treat every situation as a life-and-death matter because you'll die a lot of times. Write that down.”³

Like Timmy, I used to have a tendency to take life too seriously, especially where my job was concerned. Because I was insecure about my standing at work, I responded defensively to constructive feedback, overreacted when I made mistakes, and tried to cover up my weaknesses. Unsurprisingly, I wasn't on the top of everyone's list of picks when new projects or opportunities arose.

Fortunately, I discovered a mentor in my boss at Google who helped me realize the error of my ways. When I saw how he handled work situations with relative levity and ease, it dawned on me that I was making life overly difficult for myself. By mellowing out and seeing the lighter side of things, I've also discovered some unexpected benefits, like stronger connections with colleagues, greater stamina, and improved job performance. Best of all, I was able to build my resilience – a skill that has helped me stay true to my core career and financial goals, while opening me to opportunities for improvement.

When I asked Ramit Sethi, author of I Will Teach You to Be Rich, what one piece of advice he would give his 21-year-old self, he said, “I'd tell myself to loosen up and have more fun. When I look back, and when I was most rigid, I was less successful. The times when I was most flexible were when I was most successful, and that is true in relationships, finance, and careers.”

Do a Schedule Audit

Most of us have no idea how we spend our time – even if we think we do. In her book 168 Hours, author Laura Vanderkam suggests people track their schedules in 15-minute increments for a week to understand what activities they're doing, and for how long.⁴ Vanderkam says people are often surprised to discover how they actually spend their time. Once you do, you can identify opportunities to streamline your schedule, whether by changing the timing or frequency of certain activities, or completely eliminating them.

When I did this exercise myself, I realized I was wasting a lot of time between meetings that were spaced out by a couple of hours or less. Because those intervals weren't quite long enough for deep, strategic work, I'd often find myself surfing the web, perusing the Facebook updates of people I didn't care about, or online shopping, instead of being productive. So I decided to conduct an experiment of sorts and see what would happen if I instead bucketed similar activities together – for example, by scheduling all of my meetings back to back while blocking off several consecutive hours for strategic assignments each day.

The experiment worked even better than I had hoped. Not only did my new approach help me decrease the amount of wasted time between activities, but it also reduced the switching costs that I had been incurring by reorienting myself between different types of tasks. I encourage you to try bucketing similar activities yourself. If your experience is anything like mine, you might be amazed to discover how much more time you gain, both at work and in your personal life.

Schedule Personal and Professional Activities in Your Calendar

Most of us use an online calendar application at work to help manage our commitments, including meetings and personal appointments. But I'd guess that very few of us are using calendars in the same way outside of our jobs. Maybe we should be.

Mike Steib, CEO of the online marketplace Artsy and author of The Career Manifesto, recommends using a calendar to schedule all parts of your day. “Block off every hour of your day in your calendar for something necessary or important to you, even sleeping, eating, and exercising,” says Steib. “It may feel awkward at first, but over time, this system will change your life by helping you align your personal time with your true priorities, and making you more productive.”

I've benefited from this strategy myself. In particular, I used to have a habit of letting my weekends escape me by watching the Back to the Future trilogy on repeat (yes, even Back to the Future 3). But when I began scheduling all of my activities into my calendar, I was able to stay on track with what I really wanted to be doing and reclaim my personal time. After a few weeks had passed, I could also reference my calendar to figure out what schedule worked best for me. For example, I found that mornings are the best time for me to work out, I need one to two hours to recharge after a big meeting or presentation, and I can't write for more than four hours at a time.

As an extra bonus, this strategy allows you to look back at how you spent your time for nostalgic purposes. While looking back at my schedule, I've been reminded of great dinners, nights out with friends, and some milestone events.

Make the Most of Mornings

I used to look forward to sleeping in on the weekends. After a long week of classes or work, I felt like I deserved the chance to snooze until 11 a.m. Not anymore. After auditing my schedule and calendaring my personal and professional commitments, I discovered that mornings are often a goldmine for me to complete tough tasks.

Scott Miller, Executive Vice President of Business Development and Chief Marketing Officer at FranklinCovey, says he's always been a morning person, but recently changed how he thought about his mornings. He explains, “Instead of just being productive in the mornings, I'm beginning to think about not just how much I can accomplish, but specifically what I should accomplish. I think about what activity, if completed early in my day, would make me more productive, less stressed, and more relaxed for the remainder of the day. As you can imagine, the answer is often tackling a hard task, or something I've been avoiding.”

But you don't have to be a natural early bird like Miller to maximize the morning hours. Think about how you currently spend this time and what you may be able to achieve instead if you restructured your schedule. Then give it a go! You very well might discover that you're able to accomplish more during the mornings than any other time of day because you're refreshed from a night of sleep and lack the distractions that naturally arise during work hours.

Silence the Critics

Along your journey, you may face criticism from close friends or family or people you don't even know. I've certainly received my share of unwanted, and often unqualified, feedback – especially around some of my career decisions.

For example, when I decided to change industries after losing my job in banking, nearly everyone I knew had strong opinions that they couldn't resist sharing. Friends, family, and former colleagues often exclaimed, “Are you crazy? Why would you want to leave finance? Don't you like making good money?” Several people even declared, “There's no way you'll be able to transition to a career in tech – why would a tech company hire you?!”

People also gave me the third degree when I first launched a financial planning firm while working full-time at Google. “Why would you want to do that? Isn't that going to take a lot of time? And how much money can you even make from doing this?” they'd ask. Looking back, I realize that many of the comments were based on the person's limiting thoughts, or myths they believed about work and money. These ideas may have influenced how they lived their own lives – perhaps to the detriment of their happiness. But at the time, these subtle and not-so-subtle jabs would inflict me with self-doubt.

James Clear, author of the bestselling book Atomic Habits, recognizes the challenges of rebounding from criticism. He says, “A lot of times, criticism can be subtle, and someone may not even know they're criticizing you. When dealing with criticism, you're faced with the decision of whether you sacrifice the relationship or your goal. If a friend or family member is criticizing you, it's tough because both the relationship and goal matter.”

But as I've seen for myself, critics are everywhere, so we need to be prepared for how to handle them in healthy and productive ways. Clear advises, “Depending on your comfort level, one strategy could be to simply use open communication. Another strategy, which could be used with people you know and strangers, is to praise the good and ignore the bad. When someone supports you, praise that person for it. When someone criticizes you, try to brush it off. Regardless of the source, focus on the road ahead rather than the criticism, and use those situations to recommit to your work and goals.”

Personally, I've found the “praise the good and ignore the bad” strategy particularly effective. When my wife praises me for a job well done, I make sure to thank her for acknowledging my efforts. When she's critical of me for not emptying the dishwasher (hypothetically speaking, of course), I take a deep breath and try to just let that comment go. Praise the good, ignore the bad.

Combat Social Pressures

Social pressures are another inescapable part of life that can make us act against our true desires. Remember those days back in middle school when we draped ourselves in flannel shirts and baggy jeans, just because everyone else was doing it? That's the power of social pressure, my friend.

Because social pressures are so influential, we need to be very conscious about who we let into our lives. Or, as personal development expert and motivational speaker Jim Rohn puts it, “You are the average of the five people you spend the most time with.”⁵

On that note, I encourage you to surround yourself with people or groups who share the goals you've set for yourself. For example, if you want to save more money, you might benefit from getting to know people who enjoy low-cost activities, like running or reading, instead of high rollers who insist on getting bottle service every weekend. By seeking out people with similar lifestyle choices, you will be less tempted to jump ship for the sake of social approval.

Going back to Rohn's comment, I suggest you take a moment and think about the five people you spend the most time with. Do you feel better or worse during and after you hang out with them? Do their interests and goals align or run counter to the life you want to live?

Stop Comparing Yourself to Others on Social Media

Social media can be a double-edged sword. On the one hand, it helps us to stay up to date on the lives of people we care about, keep tabs on old acquaintances, and even confirm that the randos who email us are in fact real people. On the other hand, though, it can trick us into wishing we had other people's digitally perfect lives.

It's a fact that the stories we follow on social media are misleading. In a 2012 study of more than 1,000 Swedish Facebook users, researchers found that participants were more likely to post positive updates about themselves than negative ones.⁶ That makes sense – whether online or offline, we generally like to display ourselves in the best light possible. But the researchers warn that social media use can quickly turn into a comparison game, with unhealthy consequences for everyone involved. Their paper notes, “When Facebook users compare their own lives with others' seemingly more successful careers and happy relationships, they may feel that their own lives are less successful in comparison.”

To combat this, Clear says, “Don't compare your full movie to someone else's highlight reel. Unless you want to change places with someone wholesale, it doesn't make sense to compare yourself to them. You may see a lawyer posting nice vacation pictures on social media, but what is not so apparent is the 80-hour work weeks they had to endure to pay for that trip. Clarify the trade-offs necessary and don't cherry pick successes from other people's lives, otherwise, you're just comparing apples to oranges.”

My personal advice? Consider hiding status updates from anyone who isn't in your inner circle. Many social media platforms, including Facebook, allow you to do this without the other person knowing. This strategy allows you to enjoy the benefits of social media while sparing you the incessant feed of self-aggrandizing posts that may make you feel bad about yourself.

Know When to Say No

I used to have a hard time saying no to people, especially at work. Like an obedient dog, I was quick to drop everything I was doing to fetch other people's stuff. “Can you do this last-minute assignment that is probably really tedious, and is due tomorrow morning?” Sure, sign me up! “Do you know where I can find this figure?” Absolutely, let me spend the entire day trying to track that down for you!

While it felt good to say yes in the moment and help other people out, doing so forced me to say no to working on more strategic projects, spending time with friends and family, and occasionally catching some needed R&R. You can probably see where this is going. Because I was so quick to say yes, I reached a point when other people's needs and agendas started to take precedence over my own – a dynamic that created significant and unnecessary stress for me.

The good news is that even “yes” people like me can reclaim their schedules. To do this, Miller recommends asking yourself multiple times a day whether what you're doing is the best use of your time – which, in a work setting, probably means doing tasks that meet the top needs of your clients and your organization. Miller reflects, “As I face this test multiple times a day, I'm becoming more courageous about saying no. It often means saying no to otherwise good projects, so I can say yes to something that could have an exponential impact on my learning, competence, or brand.”

One could say that I've become a lot more catlike in recent years by following Miller's advice and exhibiting more independent thinking. In particular, I pause before responding to work requests and ask myself whether I'm best positioned to fulfill the task at hand, and what other assignments it will require me to put aside. This technique has allowed me to exert more control over my schedule, without losing sight of my company's big-picture priorities. Needless to say, I'm feeling a lot more Zen these days (relatively speaking).

Stay Mentally Fit

I'm sure you've had experiences when you didn't know if you could possibly manage to complete everything on your to-do list. For me, that was a typical Monday through Sunday in finance. In those situations, I'd usually jump to the conclusion that I'd have to work around the clock to get whatever I was working on across the finish line.

In retrospect, I realize that I probably could have been a lot more productive by periodically stepping away from my work, instead of always being on the go. I'm sure that 25-year-old Roger would have been skeptical of this approach, however. My response probably would have been something along the lines of: “What, take a break when I have so much stuff to do? In your dreams!”

Rachael O'Meara, author of Pause, recognizes the challenges of putting on the brakes when we're feeling overwhelmed – even though doing so could actually help us achieve our goals. She explains, “We often resist pausing because we think we will look like slackers, or we feel guilty about not charging forward in what we set out to do. In our always-on culture, especially in the western world and corporate life, we are rewarded for our never-ending to-do lists and our rapid pace.”

O'Meara says that simply taking four 15-minute breaks a day can enhance your creativity, renew your spirits, and engage your senses. In particular, she says that shorter but more frequent breaks are more beneficial than long pauses if you want to boost your productivity.

In my own life, I've found that I can focus intently on a task for only so long. I often feel a lot less stressed by building in breaks to recharge and “just be” – whether that means writing in a journal, working out, being present while sipping a cup of coffee, or turning off my digital devices. Just remember: work will always wait for you, but peace and happiness require finding.