Leveling Up
12 Questions to Elevate Your Personal and Professional Development
By Ryan Leak
Category: Productivity | Reading Duration: 20 min | Rating: 4.3/5 (48 ratings)
About the Book
Leveling Up (2022) is a personal-development guide structured around 12 questions that prompt honest self-assessment across work, relationships, habits, and purpose. It blends stories with practical exercises to help you take ownership of growth, refine your definition of success, and build the courage, feedback loops, and rhythms to move forward.
Who Should Read This?
- Ambitious mid-career professionals seeking actionable growth frameworks
- Overstretched managers building courage, feedback, and accountability
- Anyone wanting practical, story-driven self-improvement
What’s in it for me? Ask the right questions to redefine success, grow faster, decide smarter, and enjoy life.
Ambitious careers run on checklists – hit the target, earn the title, repeat. But somewhere between late-night emails and next-quarter goals, you might start to wonder whether the ladder you’re climbing leans against the right wall. This is where a smarter approach helps. Instead of pushing harder on autopilot, pause and ask better questions that realign success with your values, sharpen your impact with other people, and make room to actually enjoy the life you’re building.
The result is practical progress: clearer goals, steadier relationships, bolder decisions, cleaner ethics, and a habit of joy that doesn’t wait for perfect conditions. In this Blink, you’ll work through a set of practical questions that reshape how you aim, relate, improve, decide, and enjoy. Each question does a specific job – clarifying success, revealing your impact, guiding progress, prompting ownership, sizing risk, grounding integrity, and reclaiming joy. Let’s start with the Vision Question: what’s your definition of success?
Chapter 1: Meaningfully define success to become someone you’re proud of
Looking back at earlier versions of your life is a good reminder that yesterday’s “must-haves” age fast. Trends come and go, and so do the things we once chased, which is why the Vision Question matters: how do you define success? The point is to notice how past desires can still steer today’s decisions long after their shelf life has expired. From there, zoom out and admit you didn’t invent your scoreboard in isolation.
Family background, community norms, identity, industry standards, and the attention economy all push strong expectations. They create default targets that feel natural because they’re everywhere. When those defaults go unchallenged, you can work hard, hit milestones, and still feel strangely off, because you were playing by someone else’s rules. Try to build an internal definition of success that’s specific enough to guide choices. Pick goals with specific outcomes so you know when you’ve actually won and can celebrate, instead of sliding into endless “more. ” Keep an eye on the tradeoffs, because professional wins lose their shine if they hollow out your personal life.
Achievements that cost closeness with the people you love won’t feel like success for long. There’s one more layer that keeps the whole thing honest. Shift part of your definition from what you get to who you’re becoming. Choose the kind of person you want to be known as, then back it with visible habits that show up at home and at work. When you anchor outcomes to character, your targets support your relationships rather than compete with them. In the end, the Vision Question asks you to learn from the past, reject inherited yardsticks, name clear goals, protect what matters most, and measure success by both results and the person you’re becoming.
Chapter 2: Self-awareness means knowing how others actually experience you
Do you have a coworker who clogs inboxes with reply-all threads, hijacks meetings with tangents, and misses cues when the room is done? That isn’t helpful communication; it’s poor judgment about audience, time, tone, and impact. This is when the Self-Awareness Question comes in: how do people actually experience you, day to day, when they’re on the receiving end of your behavior? Most of us overrate how aware we are, and the more certain we feel, the more likely we’re missing something.
A big reason is the private narrative we run that casts us as the hero and everyone else as the obstacle. That habit turns other people into the problem, when the real work sits with our own patterns. Owning that fact opens the door to actual growth. Self-awareness has two parts. Internal awareness is being able to name your values, motives, emotions, triggers, strengths, and weaknesses. External awareness is understanding how those same things land with other people.
These skills don’t automatically come as a pair; you can be reflective and still oblivious to your effect, or read the room well and still be unanchored inside. To overcome this, treat awareness like fitness – ongoing and practical. Reflect on your roles and contexts, and imagine the real experience of being on the receiving end of your emails, meeting style, parenting, and tone at home after work. Watch small signals like body language and timing, because those shape how people feel around you.
Then ask someone else. Choose candid voices at work and at home, invite what’s good and what’s hard about you, listen without defense, and turn the themes into specific start, stop, and continue behaviors. Try this today: write down what you think it’s like to be around you at home and work, then verify with one trusted person in each place. The Self-Awareness Question is a commitment to replace flattering stories with accurate ones that reflect how others actually experience you.
Chapter 3: Progress beats perfection when you own your growth
World-class competitor Michael Jordan has said his daily contest was with his own potential, not with other players. That spirit frames the Self-Improvement Question: how can you get better? It shifts success from chasing the title of greatest to making steady gains you can control, which matters as much in relationships as it does in your career. Aiming to be the best sounds inspiring but leaves most people discouraged because wins at high altitude are rare.
Progress is a healthier target. Move from awareness to action by turning what you know about yourself into small, visible upgrades. Keep attention on what you can influence today. It’s common to blame leaders, tools, or a partner’s habits, yet momentum starts with basics you control – being on time, closing loops, and showing up well in everyday interactions. Owning controllables is where improvement begins. Protect that effort with five kinds of insurance – simple safeguards you build into your habits to cut the most common risks that derail improvement.
Irrelevancy insurance keeps you learning new skills so you don’t stall as the world changes. Ego insurance reminds you that past wins don’t excuse weak habits in teamwork or empathy. Comparison insurance turns others’ excellence into ideas to adopt, while stepping back when metrics trigger envy. Offense insurance helps you invite feedback and handle it without becoming defensive. Finally, roller-coaster insurance steadies you through highs and lows by requesting input proactively and sorting what to keep, test, or ignore. Make it practical.
Write one specific upgrade for work and one for home this month. Text three to five trusted people the exact question – “how can I get better? ” – take notes as they answer, and agree on one thing to start, one to stop, and one to continue. In the end, this question is a daily decision to measure success by progress you can prove.
Chapter 4: Own your part to build trust and move forward
When everything goes well, people line up to take credit; when outcomes slip, fingers fly. That’s where the Humility Question comes in: what mistakes can you own? The starting point is accepting that you’re the common thread in every conflict and rift, which means there’s almost always something you can take responsibility for. Humility begins with a mental shift toward intellectual humility.
Enter hard conversations willing to say you could be wrong. Our culture rewards certainty and our brains chase confirming evidence, so error feels threatening. That stance quietly damages teams, families, and friendships because many situations allow more than one valid point, and winning an argument can cost a relationship. Adopting a modest posture opens space for perspective, reduces defensiveness, and makes real ownership possible. Ownership works best when it’s quick, specific, and repair oriented. Don’t wait for resentment to harden.
Name exactly what you missed, apologize without hedging, and state how you’ll prevent a repeat. Assume your share is larger than it feels. Start with one person you likely owe rather than broadcasting generic apologies. Expect unevenness; sometimes you’ll own your part and others won’t. Do it anyway, because your growth isn’t contingent on their response. In healthy teams, multiple people volunteer responsibility, the hunt for a fall person ends, and problems get solved faster.
Start by reviewing the last month and pick one relationship to repair. State what you did, say sorry, and add a prevention step you will actually do. In the next disagreement, open with the words – “I could be wrong” – then acknowledge one point the other side may have right before offering your view. Over time, be slow to claim credit and quick to apologize. The Humility Question is a daily choice to own your part, protect trust, and keep relationships – and results – moving forward.
Chapter 5: Advancement requires taking smart risks in a changing world
Do you remember The Game of Life, with its tidy path through marriage, parenthood, and a steady career? It’s a fun script, but many lives today don’t look like that board. Prices are higher, timelines stretch, careers zigzag, and shocks can flip plans overnight. That’s why the Potential Question matters: what risk do you need to take to move forward when the old guarantees are gone?
The years of the pandemic showed that waiting things out is a gamble too. The people and teams that kept momentum were the ones who adapted fast, learned new tools, tried alternatives, and kept going after missteps. Change fatigue is real, and yet change keeps coming, so treat risk like a disciplined practice rather than a once-a-decade leap. Start by challenging the reflex of “we don’t do that here” or “that’s not me. ” Habit lines keep you in yesterday’s playbook, while today rewards legal, values-aligned experimentation. Every option carries trade-offs, which means inaction has a cost, so compare the risks of action with the risks of inaction and pick the move that expands your options.
Make risk workable with three habits. Stay a student of the future by learning skills outside your lane and pivoting when the evidence points to a better channel. Match experiments to your resources and season so you can sustain them, and take the smallest viable step. Be willing to look like a beginner; frequent, small tests compound learning, and many successes start with awkward first versions.
When you miss, write the real worst case, decide whether the problem was the bet or the execution, and adjust. Keep taking chances on people, including second chances, because many careers exist thanks to someone who did. Try one new skill this week, run one modest, reversible experiment at work, and back one person’s next move. The Potential Question is a decision to meet constant change with calculated courage.
Chapter 6: Integrity is choosing the right thing even when no one is watching
Working from home made it easy to keep your status light on and binge a show, or sneak a job interview during paid hours and assume no one will notice. But you should be asking the Integrity Question: what’s the right thing to do? The real test isn’t whether you can get away with a shortcut, it’s whether your choices build trust with those who count on you. People can usually sense when something’s off, even without proof, and that feeling erodes credibility fast.
Small compromises – padding an expense, shading a number, letting bias steer a hire – don’t stay small; they compound into lost trust, stalled opportunities, and the uneasy habit of watching your back. Integrity means being the same person in public and in private. Doing the right thing gets harder in cultures where backstabbing or inflated metrics are rewarded, yet your standard is still your choice. A practical way to hold it is to anchor decisions to good intentions for the right reasons, then widen the lens from what’s best for you to what’s best for everyone affected. Some dilemmas have more than one defensible answer; when your team sees you weighing people alongside profit, they’re more likely to trust your call. Accountability locks it in.
Make your reasoning visible, invite colleagues and loved ones to question you when something feels off, and remove easy hiding places with simple transparency. Put this into action today. If there’s a wrong you can make right – a refund, a correction, a clear update – do it now. If you face a shortcut that would benefit you, decline it and choose the step you’d be proud to explain. The Integrity Question is a daily decision to protect trust by doing what’s right, even when it costs more in the moment.
Chapter 7: Enjoyment is a decision you practice every day
You’ve seen it happen: someone nails the habits, hits the targets, earns the promotion, and still feels flat. That moment sets up the Fun Question – am I enjoying it? The blueprint for achievement is well known, but without the skill of enjoyment, life turns into permanent grind mode even when there are wins. We inherit loud ideas about what happiness should look like, and comparison keeps moving the goalposts.
Many high earners don’t act like they’re doing well because they keep looking sideways. Research in positive psychology points to a more practical path. A satisfying life has three parts. The pleasant life is about savoring the past, enjoying the present, and staying optimistic about the future. The good life comes from living core virtues like wisdom, courage, love, justice, temperance, and transcendence. The meaningful life comes from purpose.
The questions so far have been about addressing the good and meaningful parts; the Fun Question asks you to claim the pleasant part on purpose. That starts with permission. If you can afford an experience you value, plan it and refuse the guilt. Use what you have instead of curating it in a box. At the same time, don’t outsource fun to expensive moments. Curiosity turns everyday life into a source of free enjoyment if you let it.
Know what you actually like, at work and with people, and tilt your calendar toward the tasks and relationships that energize you. Practice simple savoring and gratitude, so you notice what you’d miss if it were gone. Life will remain difficult. Politics, setbacks, illness, and imperfect seasons are part of the deal. Enjoyment doesn’t wait for ideal conditions; it asks what’s still good today and makes space for it. The Fun Question is your daily cue to choose joy now, in the life you actually have.
Final summary
In this Blink to Leveling Up by Ryan Leak, you’ve learned that asking the right questions is the shortest path to better results. Success lands when defined on personal terms and checked against how others actually experience daily interactions with you. Progress compounds through small, controllable upgrades, while trust deepens when mistakes are owned quickly and specifically. Smart, right-sized risks outperform waiting for perfect conditions, and integrity means choosing the step that would stand up to daylight.
Enjoyment becomes a practiced habit of savoring what’s already good, not a distant reward. Together, these questions sharpen aims, strengthen relationships, improve decisions, and create a life lived with purpose and real joy. Okay, that’s it for this Blink. We hope you enjoyed it. If you can, please take the time to leave us a rating – we always appreciate your feedback. See you in the next Blink.
About the Author
Ryan Leak is a leadership coach, keynote speaker, and entrepreneur who advises executives and teams at Fortune-ranked companies on courage, feedback, and high-performance habits. He’s best known for viral storytelling and pragmatic frameworks that translate into measurable growth for organizations. His best-selling books include Chasing Failure and How to Work with Complicated People.