The Founder’s Paradox: How to Make Difficult Work Desirable

Difficult work gets a bad rap. Tough to scope, complex to explain, and hard to deliver — I am sure you can think of some projects that would fit this description. When you are deep in it, the effort to break through can be tortuous. But I would wager that these projects are also some of the most impactful too. Either because of what you achieved or what you learned.

Difficult work is often avoided, when it should be eagerly sought out.

As a founder, you not only pursue difficult work but you also find the adventure itself rewarding. Building a business demands that you relish and are willing to do the most taxing work. An appetite for the hard stuff defines the job.

Powering through difficult work, meaningful insights, and often significant achievements. That is because deep study and knowledge leads to not-obvious-what-is-right solutions for challenging problems. Knowledge gives you the ability to see what others do not and a vision for what to do next.

Exceptional outcomes take big effort — the reward starts from the inside, but should be recognized from the outside too.

As I have noted, founders must gravitate to the hardest work. But that does not mean that the team will naturally follow. Even the most charismatic among us cannot create sustainable motivation, curiosity, or drive for excellence in others where it does not naturally exist. So it is up to you as a leader to seek out those who desire it as well. It starts with the first hire and every hire after that.

The more you grow, the more difficult work there will be. Others need to find it inherently fulfilling too and know that grappling with it and gaining mastery is rewarded. Your responsibility to the people who join you on the adventure is to create a culture that makes that possible. You can best do that by:

Transparently sharing goals

Even with an expectation of high performance and a group of people willing to put forth their best effort, you need guardrails up. You want to be sure that effort is going towards what is most important. When goals are shared clearly, then there is no confusion.

Not welcoming egos

I suggested earlier that it starts with your first hire. Hiring motivated people who are resilient is what you want. But you could easily end up with a business run by brilliant jerks. Strive to create a team environment where high performance is demanded without the trappings of a “me-first” mentality. Teams that share an insight and operationalize it win, not the first person to see clearly.

Putting frameworks in place

Establish a model for what success looks like — both in effort and outcomes. You should have values, team structure, and workflows in place that allow great work to be done. Script how repeat work should be performed. Do it because it creates space for creativity. You need room for smart people to develop the future.

Freely providing support

Difficult work is, well, difficult. Hiring motivated experts does not change that reality. But you can cultivate an environment where folks feel secure asking for help when it is needed. That can only happen if there are actually teammates who will catch them if they fall. Knowledge is shared without reservation.

Celebrating success

Everyone wants to feel their work matters and is appreciated. And this is where many leaders go wrong, assuming that incentives or perks have an impact. Folks should be well compensated for their work. But most people would rather be recognized by their manager publicly or thanked by a coworker than to have a free lunch on Fridays.

Boldness, curiosity, and grit — these are the traits of people who find difficult work desirable. 

If you are an entrepreneur or aspire to build your own business one day, then you are likely nodding your head. But I think any ambitious person who craves meaningful work would agree. Creating lasting value is a worthy adventure, yet often hard-fought. Helping others find sweetness in the uphill climb is the key to a sustainable business — as well as sustainable individual happiness.

Read more of The Founder’s Paradox.