“I smash this verse, and I swag and surf”
‘Lil Wayne, “Swag Surf

When your career isn’t in an ideal place, it’s easy to feel powerless or paralyzed. I get it; I’ve been there. But realize that you indeed have the capability to improve your predicament. The key is to take an entrepreneurial approach: manage your career the way an entrepreneur brings a startup to life, from the big idea(s) to the founding of a company to making a business successful. And remember to factor in setbacks and pivots.

Your career is your startup, the “professional you” that you want to launch to the world because it adds value. Your career startup is what drives you; it gets you out of bed in the mornings. You are always looking for opportunities––connections, promotions, knowledge––to help you advance. You are intrepid but realistic. You always do your homework.

If you’re feeling stuck in your career, your homework is a SWAG analysis. I created the SWAG analysis while at my first venture firm. It’s a framework that serves two functions: self-evaluation and managing upward.

– Self-Evaluation: Since you’re always changing throughout your career, you should get into the regular habit of self-evaluation. It’s an opportunity to revise or reinforce your career aspirations.

– Managing upward: If you’re looking to advance at a company, the SWAG analysis is a good communication vehicle to your managers. Proactive upward management is especially important if you’re at a small to mid-sized companies that doesn’t have a formal review process. In many cases, your manager may not have the time to focus on your career advancement, so it’s up to you to take control.


There are plenty of well-documented benefits to writing things down. By mapping out your SWAG analysis, you should achieve clarity on where you are in your career today, where you’d like to be, and what you need to improve in order to fill the gap. You might not know straightaway your next steps, but I guarantee that after the initial SWAG analysis, the ideas will starting flowing.

If you’re looking for advancement at a company, set up a meeting with your manager(s) and present your SWAG analysis. This serves four purposes:

– You’re showing your managers you are motivated to grow professionally.
– You’re demonstrating that you have self-awareness on your strengths and weaknesses.
– You’re providing documentation of your accomplishments.
– You’re emphasizing that you’re focused on results.

Remember: you’re the entrepreneur of your own career startup. You’re empowered to seize opportunities for change and advancement. But first, do the SWAG analysis.