Sometimes my coaching clients will ask a tough question that stumps me.

As I was preparing for the end of a year-long coaching engagement, a coaching client asked me to share advice that I wish someone had given me earlier in my professional career. I thought this was a unique twist on the question “What advice would you give your younger self?” But I didn’t have a good answer for the question. And given that I started my professional career about three decades ago, it seems like an appropriate time for me to reflect on advice that would have saved me from angst and anxiety while also propelling me forward faster.

My client’s question was actually a tough one for me to answer because I have been incredibly fortunate and privileged throughout my career. And often we think less about our hard-learned lessons than about our successes.  After mulling it over for several days, however, I identified three ideas that I sincerely wish someone had shared with me back in the early 1990s. Of course, this advice is also relevant to me today, as I look out on the final third of my career.

Be bolder and humbler in everything you do

Throughout my career, I have not always set bold goals for myself as a professional, for my department as a manager, and for my organization as a leader.

As an example, while running an LGBTQ center in Philadelphia, I spent the better part of six years pursuing some significant facility projects that lacked a clear and ambitious vision. I raised a couple million dollars in capital funding, allowing our Center to make the building more accessible, but not fully accessible. We were also able to replace an aging heating and cooling system, and we literally shored up the foundation of the building. 

If I had been bolder, however, the goal would not have been piece meal improvements and enhancements. Instead, we would have raised many more millions of dollars to knock down the building and erect a modern facility that our community truly deserved.

A second instance of needing to be bolder happened when transitioning from my first job at a family service agency to my next job at a homeless service organization. Throughout that transition, I wasn’t nearly bold enough. At the family service agency, I had grown the grant portfolio from $250,000 to about $5 million annually, and in the process also built a small grant department that I supervised. After about 6 years, I felt ready to become a development director and landed my first development director job offer with this homeless service agency. 

I accepted a 25% salary decrease to take the job. As an early career professional, that 25% salary reduction had long-term impact on my own financial well-being, and it was four more years before I finally returned to my old compensation. I wanted to be a Development Director; I was ready to be a Development Director; and I should have been bolder by holding out for an organization willing to pay me a fairer wage for the position.  

I also would have been far humbler in all that I did. Often, my own hubris and ego have been my own worst enemies. I will always remember when the first big grant project I was leading was at risk of not succeeding. After months of partnering with the program director to plan the implementation of this six-figure Federal grant, we opened our doors for the first day of service and not a single client walked through them. In my early 20s, I couldn’t imagine a more disastrous scenario, and immediately set to work trying to fix our outreach. 

This “failure to launch” happened very early in my career before e-mail was commonplace in small and medium sized nonprofits. But I worked feverishly into the night drafting alternate outreach plans, leaving program staff multiple voicemails about tasks they needed to take the following morning to fix the issues with outreach.  

To be clear, while I wrote the grant proposal that funded this program, I was not the program director. I overstepped my boundaries. I should have acted with more humility by writing my ideas down and sharing them with  the program director the next morning. 

My brash actions not only lacked humility but I also alienated my colleagues and the program director. Being humbler in how I approached this would have made me a better team member and a better peer leader.

Actionable Advice: In being bolder, it’s important to set goals that actually scare you (just a little bit). After all, a goal you feel confident about achieving isn’t a goal – – – it’s a milestone.  Additionally, it’s important to temper strength and achievement with humility. This will ensure you build relationships that enable you to achieve those big bold goals. 

Be choosier about the jobs you accept

My career spans about three decades – two as a nonprofit employee and one as a nonprofit consultant. During the 20-year stretch as an employee, I worked for five different organizations doing everything from case management to grant writing to development director to executive director. 

Of those five employers, three of the organizations I chose to work for were a good fit. That means I was the right person to fill the nonprofit’s open position, and their organizational culture and opportunities were the right ones for that stage of my career. 

Of course, this also means that I wasn’t well-suited for two of those positions, or 40% of all of my professional employment. In the first of those positions, I was literally only at the organization for about 13 months. I did not feel seen, heard, or included as a gay person within that organization, and I didn’t feel fairly paid. Frankly, I saw enough signs that this would be the case before accepting the job, but convinced myself that it would be different after I’d worked there a while. 

The second and final time I accepted a job that wasn’t right for me was actually my last position as a permanent executive director. I’ve talked a lot on the blog and podcast about why this organization wasn’t a good fit, and I’ve also publicly discussed the many ways that I contributed to the issues I faced as executive director of that organization. But one of my main critical mistakes was accepting the job. 

I’ll always recall that interview. After a full day of interviews with the Board and staff, several red flags appeared. Two biggies were that only the search committee chair was present for my Board interview and instead of a private room, it was conducted in a hallway alcove.

Warning bells were ringing in my head that morning, and I walked away from the interview thinking that I was not the right leader to support and coach them. After returning home to Philadelphia, I called the search committee chair to withdraw from the recruitment process.

She expressed surprise, let me know that I was their top candidate, and did a “hard sell” that this would be my dream job. I let myself be sold a fiction that I didn’t believe. And it turns out my gut was right. I wasn’t the right person to lead that organization or that staff. 

I gutted it out for almost five years. The organization grew significantly under my leadership, but the cost to me and to the team members was simply too great. I often wonder how my life would be different had I stood by my first decision to withdraw from consideration. I would likely still have transitioned to consulting, but it would have been far less painful. 

Actionable advice:  The next time you’re looking for work – don’t settle. Don’t settle for the “good enough position,” the “okay pay,” or the “could be worse boss.”

Be a firm leader that exudes kindness and compassion.

As both a manager and a leader, I often struggled with balancing the delicate tightrope of being clear and setting firm boundaries, while also demonstrating that I authentically care about the people I work with. 

My personality style is very task oriented, and I love to get stuff done. Unfortunately, the  GSD personality is far more likely to be transactional in working with others. 

• • • • “Is it done? Yes or no?” 
      • “I saw you finished project X. Can you do Y by Tuesday?”
      • “I’ve written this proposal in 15 hours, why does it take you 25 hours?”

This management style doesn’t lead to long-term, productive, and trusting relationships. Consequently, earlier in my career, I would set firm boundaries and come off as an A**hole. Or I would be overly flexible at the expense of our organizational goals and achieving the mission. The tightrope was too difficult and too scary to walk. 

I wish someone would have shown me how to be my authentic, task-oriented self while also truly caring about and for the people around me. Like every other piece of advice shared in this post, this would have saved me and everyone around me a lot of heartache.

Actionable Advice: Imagine the people you lead or manage speaking at your funeral and aim for a eulogy that strikes a balance of “this person challenged me and supported me.” None of your mourners want to hear “this person let me get away with everything” or “I hated this person.”

I would like to think that if I someone gave me these three pieces of advice 30 years ago, I would have avoided big career mistake and experienced more joy along the way. I also know that 22-year-old Dolph probably would have listened to this advice, heard it, and then had great difficulty actually implementing it. Even if I had received this advice on a day when I was open to constructive criticism, I might still have still needed to learn these lessons the hard way!