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Male Executives On the Most Pivotal Point of Their Career

Considering you spend more time working than you ever will with your partner or family, finding happiness in your career is paramount. Unlike previous generations, who remained loyal to one company — and one company only — for decades, many modern professionals are tangoing between gigs, searching for more than just a paycheck, but a sense of fulfillment. 

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This shift in career patterns means that change has become an inevitable part of the working experience, and often, big choices, leaps of faith and difficult circumstances challenge professionals to pivot. Whether this means starting a new venture, shifting a mindset or something else entirely, this transitional time isn’t always easy but it can come with immeasurable lessons and success. 

Here we caught up with five executives to get their take on the most pivotal point in their careers, how it shaped their future success and what they would recommend to others approaching a career crossroad. 

"I retired, and started my own company”

After a decade of working as a federal trial lawyer, Howard A. Tullman had a successful and lucrative career. But, with an itch to start his own venture, he made the decision to leave his cushy, secure profession in favor of something new. This decision would serve as the right one, and would become a move that would shift the rest of his tenure. 

In 1980, he started CCC Information Services, one of the earliest computer database businesses in the country, still operating today, and valued at around $3 billion. Since then, he’s gone on to develop other database companies across a variety of industries — from insurance and real estate to music and employment. He is currently the executive director of the Ed Kaplan Family Institute for Innovation and Tech Entrepreneurship at Illinois Tech, where he shares his journey with budding founders. 

Lesson: Fundamentals Are Key

The greatest lesson in transitioning from a lawyer to an entrepreneur, according to Tullman, was realizing how diverse his fundamentals could become. “The key lesson here is that the people skills: storytelling, team-building, problem-solving, conflict management, and the personal attributes: passion, a commitment to hard work, perseverance, and principles, are the main drives of career success,” he says. 

Tullman adds that building up those people skills and personal attributes will have a greater pay off in the long run than technical skills. “Technical skills — at best — become obsolete over time and need to be replenished and refreshed throughout a lifetime.” 

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“I learned how to trust others instead of taking on all of the work myself” 

If you looked back on David Nicholson’s schedule a few years ago, it would have been jam-packed. He made a habit of working super-long hours, convinced it was better for him to finish a project or task rather than outsource it to someone else. 

But as he started co-founding his company, LivingDNA, he realized he couldn’t do everything himself, and he needed to learn an important lesson in trust. As he built up a team and watched them support not only his work, but the company's goals, he started to relax and pull back the reins. Though it may seem simple, he says it’s been a life-changing switch. 

Lesson: Don’t Be Afraid to Delegate

“As men, we like to fix things, we often see our value in what we do, how great we are at how many things we've fixed. Perhaps there is another way to feel successful?” he shares. 

By knowing when to delegate and ask for help, Nicholson experienced a big change in how he approaches his life both personally and professionally, seeing his value in how he approaches things rather than just what he does: “What if we don't value ourselves based on being the provider? What if we don't view our worth to our family, friends or society in terms of how great we are at our skills? It sounds far fetched but what if we saw that, first and foremost, the value that we bring to any company, staff member, partner or family is the depth of care we give?” 

“I stopped hustling 40 contracts and focused on one: my own”

Hustle, hustle, hustle was the name of the game for Bret Grafton. For most of his career, anyway. As he put it: he used to have 40 or so outside clients a year, all bringing a variety of projects and opportunities. Not all of them were rosy though, and as Grafton explained, he grew exhausted of taking meetings with people who seemed miserable at their jobs, and kept having moments where he thought ‘Why am I trying so hard to work with unhappy people in companies that aren’t mine?’ So, he pivoted and made a big ‘ole change: starting his own business. 

Today, he’s the co-founder and art director of SOUNDOFF Design, and to put it lightly, it’s changed everything.

Lesson: Don’t Measure Success by Status

“If your measure of success stops being about the names of the companies you're working with or some bullshit status barometer; you can get to the place where your measure of success is just about being happy and fulfilled with your work, and this pays off,” he shares. 

Grafton recommends making the hustle about you. “I firmly believe that the moment you let go of the idea of what your job is supposed to be, and completely embrace what you’re good at, what you love and what you’re willing to fully invest in. That’s when the big change happens.”

“An unexpected meeting from my boss changed my approach"

After a late Friday night out, Jeremy Straub headed into a sales meeting bright and early on a Saturday morning. He expected to start the day off slowly, but instead, he found his boss there to observe him. Considering his boss never worked on the weekend, it was out of character, and Straub felt anxious and ill-prepared. 

Though perhaps a bit embarrassing for then 20-something Straub, this experience taught him what he calls the ‘Jelly Doughnut’ theory. The concept goes that while one doughnut won’t make you fat, if you eat one a day, you will watch your waistline grow. 

Lesson: Little Decisions Make a Big Difference

Straub realized that while one bad meeting won’t hurt results, if every sales meeting mimicked that poor Saturday morning performance, it would. “From that day on, I had a new belief that the little decisions make all the difference,” he shares. “I lost 35 pounds in the next six months from that experience. When faced with a little decision, I tried to make it a good decision.” 

Whether it meant taking the stairs instead of the elevator or drinking water instead of soda, adopting this mindset allowed Straub to make great strides in his career and his health. “I didn’t give up on the last five minutes on the treadmill, I said ‘no’ to the desert. Every little decision, I tried to make the right one.”

Today, Straub is the CEO of Coastal Wealth, and he’s still thinking thoroughly about every choice. In fact, he says of the 10,000 decisions someone may make in a day, an average person makes 3,000 good ones, while a successful person takes the smart route 7,000 times. “Your job is to make a little more right decisions today than you did yesterday. And if you keep stringing good little decisions together, then you have your overnight success years later,” he shared. “Seventeen years later, it’s the little decisions put together over time that have made the most significant impact on my personal and professional life.”

“A client asked me a simple — yet eye-opening — question”

Though Spencer Hadelman started his career in marketing working for basketball players, he transitioned to an agency for more opportunity to grow. What he didn’t anticipate once he got there was that a client’s question, many years into his professional development, would change his career approach: they wanted to know about invoicing. “I explained that the invoice came from my agency, not from me directly. It turned out that they didn't even know the name of the agency or other higher-ups at the company, they just knew it was ‘Spencer’ doing the work and only had a relationship with me,” he continued. “It dawned on me at that moment I had outgrown the old agency and needed to go off on my own.”

Lesson: You Don’t Need a Big Company to Make It

With this new knowledge — and the hope of freedom and success — Haldeman started Advantage Marketing. Instead of believing his worth was found in the support of a larger company, that client gave him the self-esteem to do his own thing. “When I advise men on their career I always tell them the most important characteristic you can have is confidence,” he shares. “If you don't believe in yourself; who else will believe in you and your ideas and vision?”

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Lindsay Tigar, Khareem Sudlow