PDF Summary:I Wish Someone Had Told Me..., by Dana Perino

How often do you receive truly life-changing advice? If you’re Dana Perino, it’s a regular occurrence. Perino is a former White House Press Secretary and serves as a co-host on Fox News. In her online column, Short Questions With Dana Perino, she asked her guests to share helpful advice on career success, life purpose, and more. In I Wish Someone Had Told Me…, she compiles the best advice she’d heard, plus her own tips for success.

Our guide highlights the book’s major themes for different stages of life and the challenges you might face, from finding your purpose to becoming a leader. Throughout the guide, we complement Perino’s advice with perspectives from other experts on success, including Tim Ferriss, Jack Canfield, and Liz Wiseman.

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2. Develop personal standards. People who act with class establish standards for how they want to live, apart from the standards society prescribes. For example, if it’s common in your industry to get intoxicated at events, make it your standard to remain clearheaded.

3. Treat everyone as a unique individual. Though humans share many commonalities, each of us is a product of different genetics, experiences, and circumstances. Aspiring to know the unique person you’re interacting with helps you focus on them and make meaningful connections to strengthen your network, as Perino advises.

Master Communication Skills

Perino writes that mastering communication skills makes you valuable in any organization. You can prevent most problems by ensuring you communicate thoroughly and effectively, whether you’re speaking or writing. Clear and thoughtful communication reduces the risk of misunderstandings, lessens the need for follow-up communications, and ensures that important information reaches the right people in the right way at the right time. It also protects your reputation and relationships in the workplace.

According to Perino, to be an effective communicator, you should:

• Ask questions to fully understand what others are thinking before responding.
• Plan your message by considering who needs to hear it, what’s the best way to get it across, and how it could be misinterpreted. This ensures that people receive your message as intended.
• Opt for verbal communication when tone matters. It’s easier to convey the right emotion verbally than in writing.

More Tips to Avoid (or Fix) Misunderstandings

In Communication Skills Training, James Williams agrees with Perino that communicating effectively with others is a crucial skill—it’s how we build and maintain relationships, solve problems, and accomplish tasks. He offers the following tips for avoiding misunderstandings:

• Communicate about important topics face-to-face. Besides preserving tone, verbal communication lets you pick up on body language and facial expressions, which are important for understanding the other person’s feelings and intent.

• When you’re planning your message, identify the most concise and direct way to convey your ideas. The fewer words you use, the less room there is for misinterpretation.

• Check for understanding. In addition to asking questions to ensure you understand others’ perspectives, regularly check in to see whether the other person is on the same page as you are.

If misunderstandings still happen, Williams offers tips to salvage the conversation:

• Pause and identify the issue so you can address the misunderstanding immediately. Take a moment to figure out what exactly was said or done to cause the issue, so you know what to address.

• Be mindful, and if someone gets offended, keep your cool. Fully consider their perspective on what you might have done wrong. Then, take accountability for any mistakes.

Resolving a misunderstanding early might still save you from having to do follow-up communications, and it will ensure that the people who need to receive your message come away with the right idea—and hopefully no hurt feelings.

Know When to Speak Up…

Sometimes, being an effective communicator means knowing when to raise the alarm. Perino argues that if you notice a potential problem at work, speak up and make sure your concerns are heard, even if it feels uncomfortable. Speaking up decisively can prevent problems from escalating into crises. It also demonstrates responsibility and initiative, which are valued in any workplace. If you find yourself needing to speak up, Perino says you should first raise your concern directly with your boss. If they dismiss it, but your gut still tells you it’s potentially serious, share your concern with someone higher up.

(Shortform note: While Perino points out that employees sometimes need to raise the alarm, not all workplaces are conducive to speaking up. In Good to Great, James Collins explains that leaders need to cultivate a culture where truths can be sought and aired. One way to do so is to implement “alarm bell” systems: procedures that enable members of the management team to call a total halt to particular programs or strategies and raise concerns. Alarm bell mechanisms allow pressing facts to reach executives in a quick and unvarnished fashion. When these mechanisms are in place, team members feel more comfortable raising concerns, and their supervisors are more likely to take the concerns seriously.)

… and Know When to Hold Your Tongue

At other times, being an effective communicator means keeping quiet. Perino writes that you should think carefully before speaking. Exercising restraint will prevent you from making comments that could damage relationships, hurt your reputation, or create unnecessary conflict. Also, as former vice president Dick Cheney told Perino, keeping your thoughts to yourself allows others to feel comfortable expressing their opinions without fear of judgment. This means you’ll have the opportunity to hear and learn from everyone on your team.

To make sure you don’t regret what you say, Perino recommends imagining how a respected mentor or leader would feel hearing your words. If you’re in doubt, save your thoughts for a private setting rather than airing them publicly or in writing.

What Would Epictetus Think?

Instead of imagining how a respected mentor or leader would think about your words, how about imagining an ancient Greek philosopher’s reaction? In The Discourses of Epictetus, Epictetus goes further than Perino in recommending self-restraint. While she urges you not to say something you regret, he recommends that you speak only when needed. He writes that you shouldn’t indulge in small talk or talk about yourself. There’s no benefit to talking too much, and it uses up time and energy that you could spend in quiet contemplation. Furthermore, talking about yourself won’t teach you anything that you don’t already know. As Cheney observes, you learn by listening to others.

Most importantly, while saying the wrong thing can give people a negative impression of you, your actions will always speak louder than words. Epictetus says you shouldn’t waste time talking about your principles and your virtues—act on them instead. What other people think of your actions is irrelevant, so there’s no need to convince them that your reasoning is correct. Be confident in yourself (but not prideful), and you won’t feel the need to explain or justify yourself in the first place.

Developing Your Career

After learning the ropes, it’s time to move on up. According to Perino and her guests, mid-career is when you make bold but conscientious moves to propel yourself forward. This section explores four key pieces of advice for mid-career professionals:

1. Recognize your tenacity.
2. Set yourself up for promotion.
3. Never leave on bad terms.
4. Accept that there’s no recipe for work-life balance.

Recognize Your Tenacity

If you feel vulnerable and anxious as you navigate the challenges of your career, Perino says you should recognize your inner tenacity and resilience. You don’t need external safety measures, such as a fail-proof financial cushion, because you are your own source of security. Your education, relationships, skills, and past successes are a strong foundation that can catch you if you fall. When you trust yourself to overcome adversity, handle obstacles, and recover from difficulties, you feel less anxiety and have greater self-confidence.

To build this self-trust, take an inventory of your resources and accomplishments. Reflect on your past achievements and support systems, reminding yourself of the skills and relationships that have helped you succeed.

Build Inner Strength and a Tolerance of Discomfort

Other experts offer an additional way to build your inner strength and resilience: Develop a tolerance for discomfort. The opposite—prioritizing safety—may keep you from building a career you’re passionate about. In Tribe of Mentors (Tim Ferriss), actress Richa Chadha notes that a comfortable, low-risk life can be a trap for people with bigger ambitions. Comedian Patton Oswalt says you should get used to poor, cheap living conditions so you don’t have anything to lose and the risks necessary for career growth won’t scare you away.

But what if you’ve already established a comfortable life for yourself and therefore do have something to lose? The ancient Greek philosopher Seneca might say you should overcome the fear of total financial failure by temporarily “practicing poverty.” He conquered such fears by intentionally setting aside days to practice living below his means, eating less, wearing ragged clothes, and sleeping in a less comfortable home.

Advice from another Greek philosopher, Epictetus, may help you tap into your self-trust as you let go of material safety. He strongly emphasizes calm dignity and inner strength—in essence, don’t let anything upset or excite you. That way, you can bring your reason to bear in every situation. He recommends viewing hardships as chances to become stronger and to prove yourself. This will help you to stay in a positive state of mind instead of becoming frustrated or overwhelmed.

Set Yourself Up for Promotion

To give yourself the best chance for a promotion, Perino argues, you should make it easier for managers to envision you in a higher position. Do this by demonstrating initiative, readiness, and commitment. She recommends a strategy based on three key moves:

• Find opportunities to do the job you’re aiming for while excelling in your current role. Step in to help when colleagues in higher-level positions are absent and offer to take on additional responsibilities. This shows you’re ready to move up the chain of command.
• Communicate your career goals to your manager. This ensures that your manager understands your ambitions and can provide relevant feedback.
• Focus on skill development rather than obsessing over promotion timelines. Build your skills daily and don’t compare your growth with your colleagues’. Instead of spending energy making comparisons, spend it working on yourself.

How to Set Yourself Up for Impact

Perino’s advice aligns with that of other career success experts like Liz Wiseman, author of Impact Players. Wiseman adds that according to her research, impactful (and promotable) employees actively look for ways they can bring more value to the organization, even if it’s outside of their current job description. Specifically, she suggests the following steps, which are compatible with Perino’s advice:

1. Identify your superior’s top three priorities and your organization’s top three priorities. Then, find where they intersect. For instance, if both your boss and your organization view team skill development as a priority, you might decide to contribute to a project that focuses on this.

2. Determine how you can contribute. For example, if you’re tech-savvy, you might offer to improve a software tool for training new team members. If you don’t have the necessary skills to contribute, you can work on them to position yourself better in the future.

3. Share your plans. Write a brief statement about how you can help your superior and your organization achieve their priorities. Your superior will appreciate knowing how your contributions fit into larger goals and that you’ll continue to do your regular tasks well.

Never Leave on Bad Terms

What if your career growth takes you to a new organization? Perino says you should focus on maintaining positive relationships when you leave a job, demonstrating professionalism and gratitude. Human Resources expert Michelle Chase adds that how you handle your departure makes a lasting impression. Gracefully departing will help you build a positive reputation and ensure you have former supervisors and colleagues who can vouch for you in the future.

To ensure that your final interactions reflect your best self and work ethic, Chase and Perino recommend you do the following:

1. Prepare before breaking the news to your boss. This will likely be a difficult conversation, so plan what you’ll say in advance, including your specific reasons for leaving. In addition, decide beforehand whether you’d stay at your job with better terms of employment, or if you’re committed to moving on. That way, you’ll be able to respond effectively if you receive a counteroffer.

2. Be mindful of the team you’re leaving behind. Making thoughtful choices will leave a lasting impression of your professionalism. This includes giving a minimum of two weeks’ notice when resigning if you’re an early-career professional. If you’re in a senior or leadership role, be flexible about the timing of your departure to ensure a smooth transition. Additionally, take the time to tell your team and supervisors you value them, and avoid talking negatively about the organization and the team on your way out. If there’s an issue you think is worth raising, share your feedback in a respectful manner.

Additional Tips for Leaving a Job Well

Leaving a job on a positive note can be a challenge, especially if you’re leaving because you dislike the work environment or because you’re getting close to burnout (a topic we’ll address next in the guide). Considering how tricky this transition can be, career experts offer more tips, which may help you implement Chase and Perino’s advice:

First, reflect on whether you’re making the right choice. Before making it official with a conversation or a letter, consider whether you truly want to quit or if you might be going through a difficult season at your current job. Reflecting will also make it easier to lay out your reasons for leaving if you do decide to quit, and to provide thoughtful feedback if you think it’s necessary.

Next, choose the right time. Whenever possible, try to minimize the disruption you cause by leaving. For example, leaving two weeks before a major product launch probably won’t make a great impression on the team you leave behind.

Finally, make your departure as easy as possible for your team. Besides choosing the right time, make sure you leave your work in good condition so the person taking over can jump into your role without too much difficulty. Update any documentation that’s relevant to your role, ensure the right people have access to your files, and maybe even train your replacement.

Accept That There’s No Recipe for Work-Life Balance

Throughout your career, it can be challenging to balance your professional and personal lives. According to Perino, work-life balance is highly personal and evolves over time. What feels balanced to one person may be overwhelming or insufficient to another. Moreover, everyone struggles with managing competing demands on their time, regardless of their situation. Perino acknowledges that she doesn’t consider herself to have a healthy work-life balance and argues that society’s obsession with balance creates unnecessary anxiety.

Is Work-Life Balance Necessary?

While Perino downplays the importance of achieving work-life balance, design expert Debbie Millman takes this idea further. In Tribe of Mentors (Tim Ferriss), she argues that if you’re truly pursuing your passion, you’ll have no reason to worry about maintaining a work-life balance. The work itself will feel like all you need in life.

However, as Perino suggests, your interpretation of balance and how important it is to you is personal, so centering your work might not work for you. Some experts argue it’s wrong to think that following your passion immunizes you against burnout—focusing single-mindedly on your work can lead to burnout instead. Further, if you define yourself entirely by your work, you’ll suffer an identity crisis if you’re laid off or your job is otherwise disrupted. If you can’t feel good about who you are outside of work, losing the chance to work will make you panic. Therefore, consider making your hobbies and other non-work activities as central to your life as your work is so you can cope if something goes wrong professionally.

Though Perino says a recipe for work-life balance doesn’t exist, you can prevent burnout by making intentional choices and setting boundaries. However, remain flexible enough to handle the natural fluctuations of professional and personal demands. Perino suggests prioritizing what matters most to you and adopting practical habits that support your priorities:

• Prioritize your well-being. You can’t postpone or delegate your health, so be sure to maintain healthy habits. For example, set aside personal time on your calendar and prepay for the gym and your hobbies so you’re more likely to attend.
• Set boundaries to protect your work and personal lives. Set limits on after-hours work communication. Accept only one weeknight social commitment. Focus deeply when at work, and be fully present with your family when at home.
• Consciously choose what to spend time on. Evaluate requests on your time based on whether the activity is enjoyable, profitable, or supports a cause you care about. This ensures you’re spending time on what truly matters to you.

Additionally, political strategist Jessica Tarlov suggests putting things in perspective by using a five-year filter when you’re stressed or worried. Ask yourself whether the issue that worries you will still matter five years from now, and if not, consciously choose to release that concern.

Mixing and Matching Your Way to Balance

Since work-life balance is all about flexibility, you might apply the same approach to the techniques that support your balance: Mix and match what experts suggest until you find what works for you. For instance, putting things into a five-year perspective is helpful, but you can still benefit from zooming in more closely. In 168 Hours, Laura Vanderkam suggests reflecting on how you spend each 168-hour block of your time—one week—and deciding whether it’s supporting your priorities.

To try Vanderkam’s approach, add up how many hours you spent on sleep, work, family time, social media, your goals, and so on during a 168-hour period. Then, reflect on whether you’re satisfied with the time split between these activities. If you’re not spending enough time on work, your personal life, or your wellbeing, see if there’s a category in which you can cut down time.

Alternatively, you can assess how many hours you’re spending on activities that are enjoyable, profitable, or meaningful to you—and reduce the time you spend on activities that don’t fit any of these categories. If you’re struggling with choosing which activity to reduce or eliminate, then consider asking Tarlov’s question: Will it matter in five years?

After analyzing how you’re currently spending your time, Vanderkam says you should reallocate it according to your unique strengths in each sphere of your life:

1. At work, spend most of your time on tasks that utilize your unique professional strengths because they’ll impact your career goals the most. She recommends aiming to spend 30 hours a week on work that’ll directly benefit your career progression—and you must focus during this time, otherwise it doesn’t count. Conversely, limit the time you spend on tasks that won’t help you achieve your career goals, even if they’re part of your job description.

2. At home, spend most of your time and energy on your children and partner. Your family is your unique strength because only you can be a parent to your children or a partner to your spouse. In addition to setting limits on after-work communication and social commitments that creep into your family time, Vanderkam recommends you limit the time you spend doing housework.

3. As for your well-being, Vanderkam says you also need to prioritize your unique strengths to make the most of your leisure time. Find one to three activities you’d like to spend up to 10 hours on weekly, making sure to include exercise. Vanderkam notes that it’s both essential to your health and a unique strength because nobody else can do it for you.

Growing Into Leadership

As you advance in your career, you’ll find opportunities to become a leader. Perino and her guests argue that you can become a great leader by focusing on a vision and your team. This section will explore three key pieces of advice for leaders:

1. Choose to lead.
2. Start by listening.
3. Give genuine feedback.

Choose to Lead

Former NYPD inspector Paul Mauro says you should choose between merely managing—keeping things running and playing it safe—and truly leading, which involves breaking new ground and guiding people toward a vision. If you decide to lead, consider who you’d like to be led by, and then emulate that person’s leadership style.

(Shortform note: You might want to keep Mauro’s advice in mind before you get to a leadership position. Recall Perino’s earlier piece of advice to choose the boss, not the job. If you choose well, you’ll also be choosing a positive leadership model to emulate as you climb the ranks.)

Also, tell your team where you want them to go rather than dictating how they should get there. This empowers teams to use their ingenuity and inspires people to follow you rather than just comply. However, Mauro warns that most people say they want to lead but eventually default to managing because they get complacent in safe but unfulfilling roles. If you find yourself only managing and not leading, it might be time to look for a new role.

Choose to Coach

Ex-football coach turned business guru Bill Campbell offers a different distinction: Be a coach, not a manager. In Trillion Dollar Coach, Campbell’s former colleagues at Google explain his leadership philosophy: Good coaches employ encouragement, honesty, and caring to help every team member flourish. Business leaders should do the same, infusing their workplaces with compassion and people-first values that inspire employees to do their best work—and love their jobs. Create an environment in which team members can grow, develop, and flourish. Give employees the information and training they need, and respect and trust them to do their jobs well.

However, Campbell clarifies that there are some instances when the leader has to do more than inspire and nurture. When the team is struggling to agree on a key decision, then the manager has to step up, end the debate, and make a decision. Failure to make a decision can be worse than making a bad decision, so this is a time when leaders have to tell the team where to go and how to get there.

In addition, Campbell says you shouldn’t go to bed each night thinking about profit margins or budgets, but rather thinking about your employees and how you can make them more successful. This also offers a clue for figuring out when to look for a new role. What’s the last thing you think about before drifting to sleep: the outputs of your job or the team you’re leading? If it’s the former, Campbell would likely say it’s time to move on.

Start by Listening

Perino writes that listening without getting distracted is the most important leadership skill. This kind of listening reduces miscommunication and prevents your team from developing a reluctance to speak up that can lead to costly mistakes.

To become a great listener, Perino suggests the following tips:

• Don’t multitask while someone is talking. You can’t do two things well simultaneously, so set your phone face down on the table to prevent distractions.
• Don’t interrupt others or finish their thoughts for them. You can even place your thumb and forefinger in front of your lips to physically remind yourself not to interrupt.
• Actively ask for and listen to input from others, particularly during difficult times when clear direction and strategies are most needed.

The Benefits of Really Listening

Other authors refer to listening without getting distracted as active listening. Canfield (The Success Principles) explains that this type of listening requires more than merely hearing what someone is saying. It also includes observing their body language and demonstrating that you’re paying attention through your body language. This means making eye contact (which prevents you from looking at a screen instead), nodding, or physically stopping yourself from interrupting, as Perino and Lago recommend. Active listening also involves considering the underlying message of what’s being said and asking clarifying questions.

Besides helping you become a better leader, Canfield says active listening can help you understand your team members on a deeper level. Asking questions helps you learn about people’s dreams and fears. In addition, it helps build trust within your team when you show an interest in their ideas and provide the space to share them. This trust might help you fight the reluctance to speak up that Lago and Perino warn about. Finally, active listening can even make you more likable, because people tend to like those who take an interest in what they have to say.

Give Genuine Feedback

Finally, as a leader, you get to support other people’s careers. Journalist and author Salena Zito says your compliments can be meaningful and motivating if people earn them through hard work and high standards. You should provide honest feedback and encouragement to boost confidence, reinforce good habits, and foster a growth-oriented environment. Offer sincere and specific praise when someone does well, ensuring that your compliments are thoughtful and deserved.

Appreciation at Work: Motivation and Business Success

Canfield (The Success Principles) would likely think that Perino and Zito are right to highlight the importance of positive feedback. Besides nurturing team members’ confidence, positive habits, and a growth-oriented culture, appreciating employees is good for business. Canfield cites studies in which employees rank appreciation as their number one motivator. For example, one study shows that 46% of employees said they left a company because their employers didn’t appreciate them enough.

Given the benefits of making others feel appreciated, Canfield suggests tracking your acts of appreciation each day. Here are the steps:

1. Set a goal for how many people you’d like to appreciate each day.

2. Carry an index card with you. On the card, keep a tally of how many times you show appreciation.

3. At the end of the day, if you didn’t reach your goal, take some time to appreciate a few more people. For example, write thank-you emails to employees highlighting specific actions they took that deserve praise.