A guide to overcoming obstacles and achieving sales career development.
By Jenna Hughes
Feeling stuck in your career journey isn’t necessarily a sign that you’re failing. In fact, it may be a sign that you’re ready for more, according to Laura Gassner Otting, an author, catalyst, and executive coach.
Gassner Otting spent 20 years leading executive searches. Along the way, she helped many people navigate vulnerable moments in their career.
“My journey has been anything but linear – it’s been a series of pivots, leaps of faith, and moments of both confidence and uncertainty,” said Gassner Otting, author of the Wall Street Journal best-selling book “Limitless.”
Gassner Otting started her career in politics, working in the Clinton White House, where she helped shape national service programs. Then, she spent two decades in executive search, helping mission-driven organizations find their leadership. “That experience showed me firsthand the difference between those who succeed on paper and those who thrive.”
During her own personal career journey, Gassner Otting found that the most profitable, fulfilled, and productive individuals in companies weren’t always those who worked harder, but those who knew how to connect their work to their passions.
Gassner Otting recently spoke to Repertoire Magazine on how sales reps can achieve long-term success.
Finding personal fulfillment
If you feel like you’ve hit a ceiling, it may be time to take a step back and reassess, said Gassner Otting.
“The question isn’t whether you’re good enough. The best salespeople don’t sell – they help,” asserts Gassner Otting. “Are you proactively deepening relationships rather than just responding to what’s in front of you? Are you solving bigger problems? Are you positioning yourself as a trusted advisor rather than just a salesperson? When you shift your mindset from transactions to transformation, success follows.”
An integral part of success in sales comes from our own internal motivators. Finding confidence and voice can help salespeople to overcome obstacles, and, by pushing past internal limiting beliefs, salespeople can achieve more in their career than they ever thought possible.
Considering pointed, specific goals and desired outcomes before interacting with customers allows for preparedness in sales meetings, allowing you to connect with the customer, know your product, and drive results.
“Confidence doesn’t come from knowing you’ll never fail – it comes from knowing that failure won’t break you,” said Gassner Otting. “The best salespeople don’t have some innate, unshakable self-assurance. They build their confidence through action, resilience, and relentless curiosity.”
Generating voice and confidence
Start by identifying your own distinctive purpose as a sales rep. Is it forging trusting relationships with customers? Providing life-saving products across the industry? A work-life balance to spend much needed family time? Your purpose, one or many, guides you; you cannot be fulfilled by someone else’s goals.
Sales reps must therefore match what they do to who they are, also known as consonance, which requires creating one’s own definition of success. Consonance can be reached through the four elements of calling, connection, contribution, and control, as described in Gassner Otting’s book ‘Limitless:’
1. Calling: A gravitational pull toward a goal larger than yourself.
2. Connection: Gives an individual an understanding of how their everyday work serves their calling.
3. Contribution: An understanding of how your job, paycheck, company, etc. contributes to the person you want to be.
4. Control: Reflects how you influence your connection to your ultimate calling (such as in the assignment of projects, deadlines, and clients; offering input into shared goals, and doing work that contributes to your career trajectory).
Until you can control how connection and contribution are influenced by calling in your career, you will continue to be limited in confidence to make choices and take chances.
Once you begin the process of focusing on the four elements of consonance, Gassner Otting’s overarching piece of advice for a successful lifelong career in sales is to stay “relentlessly curious.”
“The people who thrive over the long haul are the ones who never stop learning, adapting and growing,” said Gassner Otting. “Your career is not a fixed identity; it’s a series of choices that you get to make. Keep asking yourself: ‘What excites me? Where can I add the most value? What do I need to learn next?’ If you keep pushing your own boundaries, your career will never stagnate – it will always expand to meet the size of your ambition.”
A guide to a lifelong career
Finding your own sense of purpose, or reason for which you do something, is key to success, which encompasses your career, company, personal life, and beyond.
“Everything I teach comes from what I’ve lived. I’ve had moments where I thought I was at the top, only to realize I was deeply unfulfilled,” said Gassner Otting. “I’ve had to reinvent myself multiple times and embrace the unknown.”
Stepping into discomfort can allow you to find new paths and opportunities, and may ultimately lead you to discover a more fitting, fulfilling career and personal journey.
“Eventually, through experience, I realized my true calling: helping people see their own potential and build lives that align with their greatest ambitions. That led me to write books, speak on stages around the world, and coach high achievers to get out of their own way.”
Success isn’t always about finding the perfect path – instead, it’s about making bold moves, learning along the way, and giving yourself permission to evolve.
“Often, we spend so much time climbing the ladder that we forget to ask if it’s leaning against the right wall. Too often, we chase the version of success that society, our industry, or even our past selves told us we should want – only to get there and realize it doesn’t feel the way we thought it would,” said Gassner Otting. “Real fulfillment doesn’t come from external validation; it comes from alignment. If success doesn’t feel satisfying, it’s a sign that you need to redefine it on your own terms.”