Making the Most of an Unplanned Career Break

Strategies to Stay Competitive and Interview-Ready During Extended Job Searches

Making the Most of an Unplanned Career Break

The tech industry continues to face challenging times, with layoffs affecting professionals at all levels of the industry. If you’re currently between roles, whether it’s been three months, six months, or longer, you’re not alone. Unfortunately, there’s still a perception that extended unemployment reflects poorly on the individual rather than industry conditions. Here’s how to turn an unplanned career break into a strategic advantage while preparing compelling stories for your next interview.

Reframe Your Career Break

I often see people list “career break” to cover a gap between roles. While people do this as a deliberate choice to recharge, you can also use this on your resume to reframe an extended job search. Simply listing “career break” on your resume isn’t enough. Be specific about what you’re doing with that time. Are you learning new technologies? Earning certifications? Developing new skills? This shows you’re staying engaged with industry developments and taking your professional growth seriously, even while job searching.

More importantly, each skill you develop gives you fresh material for interviews. When interviewers ask about recent learning or how you stay current with technology trends, you’ll have concrete examples: “During my career break, I dove deep into Kubernetes and earned my CKA certification. I also built a personal project using React 18’s new concurrent features to understand how they improve user experience.”

If you’re using “career break” to account for job search time, limit this approach to six months maximum unless you’re genuinely taking an extended, planned break. You can use the end of your “career break” time on your resume as an opportunity to restart your job hunt, looking fresh to recruiters.

Start a Consulting Company

Creating a consultancy demonstrates you’re still actively working and using your skills, even if you’re not employed full-time. Yes, building a consultancy is challenging, especially without strong existing connections, but it shows initiative and keeps you in the professional game.

In interviews, consulting experience provides rich storytelling opportunities. You can discuss how you navigated different client needs, adapted to various tech stacks, or solved problems with limited resources. “Working with three different clients taught me to assess legacy systems and propose pragmatic modernization strategies quickly” is far more compelling than explaining a gap in employment.

Be strategic about the contracts you accept, ensuring you can transition away if a full-time opportunity arises. Use any downtime between clients to develop new skills or pursue certifications that enhance your value proposition and give you additional interview talking points.

Build a Startup

Don’t let the complexity intimidate you; starting a startup can be as simple as developing an idea and creating a website. This approach works particularly well for senior leaders who want to demonstrate they’re still innovating and building.

The interview advantages here are enormous. When someone asks, “Tell me about your startup,” you have a natural opportunity to showcase technical decisions, product thinking, and problem-solving approaches. You can explain why you chose certain technologies, how you validated assumptions, what you learned about user experience, or how you approached scaling challenges. These conversations demonstrate both technical depth and business acumen.

Most startups fail, and hiring managers understand this. What they’ll appreciate is your initiative, the skills you’ve developed, and the concrete experiences you can discuss. Be prepared to explain your transition: “After eight months, I realized the market timing wasn’t right, but I learned invaluable lessons about modern deployment strategies and user research that I’m excited to bring to a larger team.”

Address the obvious question directly: “I’m ready to shelve the startup and focus entirely on this role. The experience taught me what I love about building products within a larger organization rather than going it alone.”

Contribute to Open Source Projects

Open source contribution keeps you coding, collaborating with teams, and engaging with the broader tech community. As a significant user of open source software, contributing back is both professionally beneficial and ethically sound.

This path creates specific technical stories for interviews. You can discuss code review processes, how you approached complex bug fixes, or how you collaborated with maintainers across time zones. “I contributed a performance optimization to [popular library] that reduced memory usage by 30%” is a concrete achievement that demonstrates both technical skill and impact.

While “open source contributor” might not carry the same weight as other options on your resume, it’s meaningful work that demonstrates ongoing skill development. Plus, becoming a key contributor to a popular project can lead to networking opportunities and potential job connections.

Volunteer Your Technical Skills

Consider leveraging your expertise for charitable organizations that need technical support. Many nonprofits struggle with outdated systems, a lack of digital infrastructure, or limited technical resources. Volunteering your skills provides several benefits:

Real-world impact: You’re solving genuine problems for organizations, making a difference
Portfolio building: These projects often involve diverse technical challenges and constraints
Interview gold: “I built a volunteer management system for a local food bank that increased their efficiency by 40%” shows both technical capability and values alignment
Leadership stories: Smaller organizations often give you more responsibility, providing examples of how you drive technical decisions and manage stakeholder relationships
Problem-solving under constraints: Nonprofit projects typically involve limited budgets and resources, showcasing your ability to deliver value with creative solutions

When discussing volunteer work in interviews, focus on the technical challenges and business impact rather than just the charitable aspect. “Working with a limited hosting budget taught me to optimize for performance in ways I hadn’t considered in enterprise environments.”

Strategic Interview Messaging

Whatever approach you choose, be prepared to explain your transition back to full-time employment confidently. Frame your experience as intentional professional development: “I used this time to explore entrepreneurship and deepen my technical skills. Now I’m excited to bring these fresh perspectives and enhanced capabilities to a collaborative team environment.”

Each path gives you concrete examples of continued growth, problem-solving ability, and professional commitment. The key is having specific stories ready that demonstrate how your career break time made you a stronger candidate, not someone who’s been out of the game.

Remember, showing that you’ve remained productive and engaged during your career break demonstrates resilience, self-motivation, and commitment to your profession; qualities any employer would value. More importantly, you’ll walk into interviews with fresh experiences and genuine enthusiasm for what you’ve learned and built.

Originally published at https://kevingoldsmith.substack.com/p/making-the-most-of-an-unplanned-career

The CTO’s Guide to Crafting a Technology Leadership Resume

Crafting a resume as a technology leader is about more than listing roles—it’s about showcasing achievements, leadership, and strategic impact. Learn how to tailor your resume, highlight cross-disciplinary management, and leverage tools like LinkedIn and personal websites to stand out for executive roles.

A common discussion with people I mentor is how to properly structure a resume or Curriculum Vitae. It comes up often enough that I felt compelled to write about it last year: “Sweat the details on your resume, especially if you are a developer or technology leader.” In the last few weeks, I have reviewed multiple resumes from folks hoping to achieve a director-level or above role. I wanted to share some lessons on how an executive-level resume differs from others in Technology.

As a technology executive, your resume is your calling card—a teaser trailer for your professional achievements. Crafting a resume that highlights your leadership journey while demonstrating value is an art form, particularly as you aim for senior roles like VP, CTO, or similar. Here are key takeaways and strategies to ensure your resume stands out.

Tailor Your Resume for the Role

Your resume isn’t a one-size-fits-all document. Different audiences—recruiters, hiring managers, or automated systems—expect varying levels of detail. To make a strong impression:

Create multiple versions of your resume:
- Short-form (2 pages or less): Use this for recruiters or direct submissions. Focus on succinct highlights that convey your biggest achievements and relevant experience.
- Comprehensive (full-length): Maintain this detailed record for Applicant Tracking Systems (ATS) or contexts where exhaustive experience matters, such as certain consulting or academic roles.
Use strategic brevity: Each version should prioritize accomplishments and impact over exhaustive lists of tasks or skills. At the bottom of the short-form resume, include a URL to your full-length resume, LinkedIn profile, or personal website for those who want more detail.
Tailor content to the role: If applying to a startup, focus on entrepreneurial accomplishments. For a multinational corporation, emphasize experience working with large teams or global operations.

Focus on Achievements, Not Responsibilities

Leadership resumes should emphasize measurable outcomes rather than generic responsibilities. This allows you to demonstrate value and differentiate yourself from other candidates. Consider these approaches:

Use metrics whenever possible: Quantify your achievements to provide concrete proof of your impact. For example:
- Replace “Managed a team of data scientists” with “Grew a data science team from 5 to 20 members, delivering a 10x cost efficiency improvement in critical business processes.”
- Instead of “Improved system performance,” say, “Increased platform uptime from 97% to 99.9% while reducing hosting costs by $500,000 annually.”
Highlight transformative initiatives: If you drove major changes—like adopting a new technology stack or transitioning a team to a new operating model—emphasize these innovations and their outcomes.
Demonstrate multi-disciplinary management: Showcase examples where you’ve managed diverse teams or disciplines, such as engineering, product, and design. For example, “Led cross-functional teams spanning software development, UX design, and data analytics to deliver a platform used by over 10 million users.”

Put Your Most Recent Role First

Your current or most recent position carries the most weight. It’s likely the first thing a recruiter or hiring manager will read, so ensure it captures attention:

Make it prominent: Place this role on the first page and dedicate the most space to it.
Emphasize scope and results: Clearly articulate the scale of your responsibilities, such as budget size, team size, and direct impact on the company.
Focus on strategic leadership: Highlight initiatives you spearheaded and the outcomes they achieved, particularly those demonstrating thought leadership, cross-functional collaboration, or innovation.

Save earlier roles for subsequent pages, reducing detail as you go further back in time. Roles older than 10 years may only need a line or two unless they’re particularly relevant.

Position Skills Strategically

Technical skills are critical, but how you present them matters:

Avoid generic lists: Instead of placing a large block of skills at the top, embed them within descriptions of your achievements. For example:
- “Led migration to AWS Cloud, saving $1.2M annually and achieving 99.9% uptime.”
Highlight relevant expertise: Tailor the skills you emphasize to the role you’re applying for. If you’re aiming for a director role in AI, showcase experiences involving ML frameworks and tools like TensorFlow or PyTorch.
Subtly include soft skills: While technical skills are important, leadership roles often require strong interpersonal and strategic abilities. Show how you led teams, resolved conflicts, or drove cross-departmental alignment.

Summarize Career Progression

Rapid promotions and career growth can be a powerful selling point, but they need to be presented succinctly:

Highlight trajectory: For example, “Promoted from Senior Machine Learning Engineer to Head of AI within three years.”
Simplify titles: If your roles had incremental changes, summarize them into a cohesive narrative. For example: “Advanced from Senior Engineer to Director of Engineering over six years, culminating in leading a 50-person team and delivering $20M in annual revenue growth.”
Emphasize leadership: Show how your roles evolved to include greater responsibility, larger teams, or more strategic initiatives.

Cut the Fluff

Hiring managers and recruiters skim resumes. Get to the point by removing irrelevant or overly detailed information. This will make your resume more focused and efficient, ensuring that only the most important details are highlighted.

Avoid generic claims: Statements like “Proven leader” or “Results-oriented professional” don’t add value. Instead, provide examples that demonstrate these qualities.
Skip common experiences: Transitioning to remote work during COVID-19 isn’t unique. Focus on outcomes that set you apart.
Reduce early-career details: Unless highly relevant, roles from over 10 years ago should only include titles and dates.

Use LinkedIn and a Personal Website for Depth

Your LinkedIn profile and personal website can complement your resumé by providing additional details and ensuring you’re findable by recruiters:

LinkedIn:
- Include all positions and significant accomplishments.
- Add media or links to showcase notable projects, talks, or publications.
- Use keywords strategically to improve searchability for specific roles.
Personal website:
- A personal website can be a dynamic portfolio, host your detailed resume, and provide links to your projects, publications, or conference talks.
- Organize your website by sections, such as Leadership Roles, Key Achievements, and Speaking Engagements, to make it easy for recruiters to navigate.
- Use your website to expand on areas that wouldn’t fit in a resume or LinkedIn profile, like detailed case studies or thought leadership pieces.

Think Like a Hiring Manager

Your resume should:

Reflect strategic thinking: Tailor information to the audience and highlight your ability to align your work with organizational goals. This approach will make your resume more strategic and thoughtful, resonating with the hiring manager’s perspective.
Demonstrate leadership: Showcase your leadership skills by using examples of team management, cross-functional collaboration, or strategic initiatives. This will make your resume more confident and assertive and reflect your leadership potential.
Inspire curiosity: Provide just enough detail to make recruiters and hiring managers want to know more about you.

Remember, the goal of your resume is to secure a conversation—not to answer every question upfront.

Advice for Aspiring Executives: Breaking Into Leadership Roles

If you’re seeking your first executive-level (Director or above) role, your resume needs to convey readiness and potential:

Reframe your achievements: Highlight instances where you took on responsibilities beyond your official role, such as:
- Leading cross-functional initiatives.
- Mentoring junior staff or peers.
- Driving strategy or innovation.
Show leadership impact: Even if your title doesn’t reflect it, focus on achievements that demonstrate leadership qualities, such as:
- “Initiated and led a company-wide migration to DevOps practices, reducing deployment time by 80%.”
- “Mentored three engineers who were later promoted to senior positions.”
Emphasize thought leadership: Include speaking engagements, publications, or significant contributions to open-source projects to showcase your influence in the field.
Network strategically: Your resume is only part of the equation. Attend industry events, contribute to discussions on platforms like LinkedIn, and seek mentorship from executives who can provide guidance and referrals.
Communicate readiness in your summary: Begin your resume with a compelling summary that positions you as an emerging leader. For example:
- “Engineering Manager with a proven track record of driving strategic initiatives and leading high-performing teams, seeking a Director role to deliver innovative solutions at scale.”

Breaking into executive roles requires showcasing your potential and articulating how your experience aligns with leadership expectations. By tailoring your resume and approach, you can make the leap into senior management.

By taking a strategic, minimalist approach to your resume, you’ll showcase your accomplishments and demonstrate your ability to communicate effectively—a critical skill for any technology leader.

Sweat the details on your resume, especially if you are a developer or technology leader

Your resume is a simple enumeration of your experience and the first sample of work you are presenting to a potential employer. Many developers neglect the quality of their resume because they aren’t comfortable with writing, not comfortable talking about themselves, or simply because they don’t think it is important.

Photo by Vanessa Garcia

Every hiring manager has things that will influence them positively or negatively about a person when reading their resume or CV. Given how critical attention to detail is for developers and technical leaders, lacking attention to detail is a warning flag for me and many other leaders I speak to.

Your resume is a simple enumeration of your experience and the first sample of work you present to a potential employer. Many developers neglect the quality of their resume because they aren’t comfortable with writing, not comfortable talking about themselves, or simply because they don’t think it is important. When there are shortages of skilled developers, hiring managers will often overlook formatting, spelling, or grammar mistakes in a resume. When the hiring manager has multiple good choices for a role, seemingly small things can make a big difference in the perception of you as a candidate.

Weaving in the Details

Remember that your resume is more than a list; it’s a story of your professional journey, skills, and aptitudes. The quality of this narrative directly impacts a hiring manager’s perception of you. So, while it’s crucial to include your significant accomplishments and skills, attention to detail helps to fill in the gaps and provide a comprehensive picture.

For example, including specific project details, like what technologies you used, your role in the project, and the quantifiable results, can set you apart from the competition. These details reveal the true extent of your abilities and demonstrate your authentic experience as a technologist and your focus on the outcome, not just the output of your work.

Evidence of Care and Dedication

Meticulous attention to detail on a resume is a positive signal to employers. It’s a testament to your dedication and commitment to excellence. On the other hand, errors, inconsistencies, or vague descriptions can give the impression of carelessness or lack of effort. Spelling and grammar mistakes, easily caught by a spelling or grammar checker in a document editor, are red flags. If you have front-end or user-facing application development experience, inconsistent or poor formatting questions your skills.

Detailing Technical Proficiencies

Specificity in listing your technical skills is another area where detail matters immensely. A generic mention of “programming languages” won’t do the job. Instead, list each language and technology you are proficient in, ideally linking them to your professional experience or projects.

Compatibility with Job Descriptions

Lastly, close attention to the job description can make all the difference. Customizing your resume to fit the specifics of the role shows a proactive and thorough approach.

How to debug your resume

Use a spelling and grammar checker.
Have a friend (preferably someone experienced in reviewing resumes) proofread it.
If you are putting your resume into a language where you are not a native speaker, have a couple of people who are native speakers read it over for tone and phrasing.
If you are unsure how to phrase something, find other resumes (or LinkedIn profiles) from folks with similar experiences to see how they express it.
If you are updating your resume with new experience, read it thoroughly to ensure that the new and old sections have the same tone of voice and style.
Once you have made your changes, put your resume aside for a day or two and then reread it with fresh eyes to catch anything you may have missed.

These things seem obvious, but I can’t count the times I’ve found glaring errors in resumes where the candidate did not follow those steps.

Don’t disqualify yourself for silly reasons!

Attention to detail in a resume could be the difference between getting your foot in the door or having it firmly shut. As a technical professional, your attention to detail should reflect in your work, and there’s no better place to start demonstrating it than your resume.

A well-crafted, detailed resume is your representative in your absence, showcasing your abilities and a testament to your commitment to precision. So, the next time you revise your resume, remember to keep the details in focus. It might just be your key to the next big opportunity.

Your resume is an opportunity to illustrate who you are as a professional and how you approach your work. Attention to detail not only elevates your resume above the rest but also demonstrates the values essential to success in technology: meticulousness, precision, and a deep understanding of your craft. The details aren’t just details; they’re differentiators.