How to Overcome Career Self-Sabotage and Build a Successful Career by Getting the Easy Stuff Right

Career self-sabotage often looks like... nothing

Most people don't fail because of complexity; they fail because they overlook the basics.

Scott Galloway emphasizes this point: "Respecting institutions, having manners, demonstrating a level of humility… these are all (relatively) easy. Get the easy stuff right" (Galloway, 2018).

Reflecting on my early career, it wasn't a lack of ambition or ability that held me back. It was a pattern of career self-sabotage. Things like unnecessary sick days, skipping networking events, arriving late, dressing down too much, or being unprepared. These weren't catastrophic failures but subtle signals of unreliability.

In today's competitive job market, such patterns can hinder professional development. This article delves into how to build a successful career by avoiding self-sabotage, drawing insights from Scott Galloway, Cal Newport, and Stoic philosophy.

The Myth of "Follow Your Passion"

The advice to "follow your passion" is pervasive but potentially misleading. Cal Newport critiques this notion, arguing that passion often follows mastery, not the other way around. In his book So Good They Can’t Ignore You, Newport introduces the concept of the "craftsman mindset," focusing on developing rare and valuable skills - what he terms "career capital" - to gain control over one's career path (Newport, 2012).

Newport explains that few people have a pre-existing passion that clearly defines their professional path. More often, passion emerges through competence, autonomy, and contribution—three factors rooted in skill, not sentiment. This idea is reinforced by self-determination theory, which shows that people find work satisfying when it provides a sense of control, competence, and connection.

Scott Galloway echoes this sentiment, stating that many successful individuals didn't start with a clear passion but developed it through dedication and skill acquisition (Galloway, 2024). He argues that the passion narrative often distracts young professionals from building tangible capabilities.

The Stoics would agree. Marcus Aurelius advised: "Waste no more time arguing what a good man should be. Be one."

This encapsulates the Stoic focus on action and discipline over introspection. Purpose is forged, not found.

A hand-drawn, textured illustration depicts a man in an orange sweater standing thoughtfully before a large cloud containing the phrase “FOLLOW YOUR PASSION” in bold orange letters. To the left, a red arrow labeled “MYTH” points away from the cloud. To the right, a blue arrow with a question mark suggests uncertainty. In the foreground, several seated figures observe the scene. The background is softly coloured with pastel-style strokes in blue, green, and beige, conveying a reflective and questioning mood. — All these people telling you to "follow your passion" rarely got there by doing so

Recognizing Career Self-Sabotage

Career self-sabotage often manifests subtly:

Chronic lateness
Avoiding networking opportunities
Neglecting follow-ups
Delivering minimal effort
Seeking instant gratification over long-term value

These behaviors send signals to colleagues and managers: this person can’t be relied on.

In his viral blog post and subsequent interviews, Galloway tells the story of a student who walked into his MBA class an hour late and was promptly dismissed. The student protested, citing a lack of clarity about the lateness policy. Galloway's reply was blunt: "Get the easy stuff right. In and of themselves they will not make you successful. However, not possessing them will hold you back, and you will not achieve your potential" (Galloway, 2010).

Stoic philosophy reinforces the idea that character is revealed in small, consistent actions. Epictetus said: "First say to yourself what you would be; and then do what you have to do."

Self-sabotage is often about inconsistency - discrepancies between who we believe we are and what we actually do. The Stoic response? Close that gap through disciplined, value-driven behaviour.

Building Career Capital Through the Craftsman Mindset

Cal Newport's "craftsman mindset" stands in opposition to the "passion mindset." The craftsman focuses on what they can offer the world. This mindset prioritizes deliberate practice, feedback loops, and a tolerance for discomfort—because excellence requires strain (Newport, 2012).

In fact, Newport draws heavily on the research of Anders Ericsson, who popularized the concept of deliberate practice. In short, doing the work isn’t enough. You must do focused, feedback-driven work that pushes your boundaries. This is how you accumulate career capital.

Career capital (those rare and valuable skills) is your currency. It allows you to negotiate better roles, gain autonomy, and eventually do work that feels meaningful. You trade competence for control.

This philosophy aligns neatly with Stoic ideas. Epictetus taught that freedom is found in mastery of self. That includes mastery of skill. As the Stoics say: Don’t explain your philosophy. Embody it.

A hand-drawn digital illustration depicts a focused craftsman chiselling the word “CAPITAL” into a large stone block on a wooden workbench. He holds a wooden mallet in one hand and a chisel in the other, wearing a collared shirt and dark apron. Above him, a vintage banner reads “CRAFTSMAN MINDSET.” The background is softly textured in pastel tones of blue and beige, evoking a sense of diligence, patience, and mastery. — Building your career capital through practicing like a craftsman is they key to realising freedom and self-mastery

Practical Strategies to Avoid Self-Sabotage

Here are practical, simple behaviors that stop self-sabotage and signal trustworthiness:

Show up early - Being consistently on time shows respect for others’ time.
Overprepare - Take initiative to anticipate what’s needed—even if no one’s watching.
Follow through - Deliver what you promised without being reminded.
Develop your skill - Allocate time weekly for focused learning, especially on skills that compound (e.g. writing, presenting, decision-making).
Ask for feedback - And make visible improvements.

According to Newport, those who practice these habits, especially in roles that don’t seem “important”, acquire the very capital that earns them leverage later. In this sense, how you show up now determines your future options (Newport, 2012).

Galloway puts it simply: "Winners endure. They show up. They improve 1% at a time" (Galloway, 2024).

Some additional tips to avoiding self-sabotage

Why Soft Skills Are Career Superpowers

Soft skills - like emotional intelligence, communication, and consistency - are not “extras.” They are foundational.

According to a report by LinkedIn, 89% of hiring managers say lack of soft skills is the main reason new hires fail (LinkedIn, 2019).

Soft skills are directly tied to trust, which influences how much opportunity others give you. Being competent but unreliable won’t take you far. Being competent and trustworthy is rare, and therefore valuable.

The Stoics would see soft skills not as tactics, but as virtues: courage, temperance, wisdom, and justice applied in a modern context.

A hand-drawn illustration features a large vintage-style balance scale labelled “Soft Skills are Career Superpowers.” On the left pan, icons represent soft skills—such as a handshake, lightbulb, heart, and checkmark—beneath a red banner that reads “Soft.” On the right pan, under a blue banner that reads “Technical Skills,” icons depict graphs, charts, and dashboards. A man in an orange shirt stands in thoughtful reflection between the two. Four people at the bottom observe the scene, highlighting the importance of both skill types in career development. The artwork uses warm tones and textured shading for a thoughtful, accessible tone. — Broad-based generalist soft skills are often a gamechanger in the workplace

Embracing Stoic Principles for Professional Growth

The Stoics teach:

Focus on what you can control - You can’t control outcomes, but you can control effort.
Train for resilience - See every difficulty as practice.
Live by principles - Let integrity guide action.

Seneca reminds us: "Life is long, if you know how to use it."

Galloway and Newport aren’t philosophers, but their strategies are strikingly Stoic: Build capability. Control what you can. Endure hardship. Focus on the long term.

Build Options, Not Idealism

Instead of waiting for your dream job, build options through skill, reputation, and reliability.

As Newport puts it: "You have to get good before you expect good things in your career" (Newport, 2012).

Galloway frames success as a function of stamina, not sparks: "The most overlooked truth in business and life is that 90% of it is just showing up consistently" (Galloway, 2024).

A hand-drawn illustration features a man in a mustard-coloured sweater standing at a fork in the road, contemplating two paths. One wooden signpost points left toward “OPTIONS,” under a sunny, open sky. The other points right toward “IDEALISM,” beneath darker clouds. Above, a large blue banner arches across the scene, reading “BUILD OPTIONS, NOT IDEALISM.” The landscape is lush and green, evoking the tension between practical growth and abstract ideals. — The goal of building career capital is to give options. Idealism narrows those options for yourself.

Conclusion: Aligning Actions with Aspirations

Overcoming career self-sabotage means shifting from reactive to intentional. From passive to proactive. From waiting to showing up.

Whether you follow Scott Galloway’s directness, Cal Newport’s evidence-driven advice, or the Stoics’ call to virtue, the message is the same:

Master the basics. Build something. Embody what you value.

Start there, and let everything else follow.

Find something you're great at