Tackling Obstacles: Turning Roadblocks Into Stepping Stones


How does the saying go? “The best laid plans of mice and men often go awry.” I love a good action plan. Goals are clearly laid out with specific steps and a timeline. Then, wham, an obstacle pops up and blocks the way.

When that happens, you usually have two choices: stop in your tracks and give up, or find a way to go around, over, or through the barrier.

Pause, Don’t Quit
I am rarely a proponent of giving up, even when the challenge feels overwhelming. Sometimes the best first step is to pause. Take a break to catch your breath and regain perspective. You can shift focus temporarily by working on a different project or spending time on something enjoyable that recharges you. Alternatively, you can disconnect completely by stepping away from structured work for a bit, taking a walk, reading a book, or spending time outdoors.

This pause also gives you space to acknowledge the emotions that obstacles stir up, which might include frustration, disappointment, or even anger. Naming those feelings can lessen their power over you. Then, remind yourself of why you started the goal in the first place. That “why” can re-energize you for the next step.

For example, a business owner working on a new product launch faces a supplier delay. Rather than cancel the launch, she shifts attention to updating her marketing materials and training her sales team. This pause not only keeps the project alive but also strengthens it.

Diagnose the Obstacle
Once you’re ready to re-engage, ask yourself, what kind of obstacle is this? Is it a temporary setback?  Sometimes you need to wait it out. For instance, during our federal government shutdown, many businesses have redirected resources to non-governmental projects until funding resumes. Recovery may take time, but the obstacle eventually moves. Is the obstacle long-term? If so, you must change your approach. This might mean finding a new vendor, learning a new skill, or redesigning part of your plan. For example, a runner training for a marathon sprains an ankle. Instead of quitting, she shifts her training to swimming and strength work while recovering. The detour keeps her goal alive in a different form.

Seek Help and Weigh Options
If the obstacle isn’t solvable on your own, don’t hesitate to call on others. Advisors, colleagues, mentors, or even professional consultants can provide valuable insights and resources that you might not have considered.

As you consider your path forward, weigh the benefits and costs of each option:

- Will this delay other goals?
- Does it require additional budget?
- Could it carry reputational risks?
- What are the potential long-term benefits of choosing this option?

Select the route that strikes a balance between feasibility and forward momentum.

Keep Communicating
Regardless of your approach, keep your stakeholders informed. Early, honest communication builds trust and often garners support, even when the news isn’t ideal. People appreciate being included in the journey rather than being surprised at the end.

Obstacles are inevitable, but they don’t have to be dead ends. With a pause for perspective, a clear-eyed diagnosis, thoughtful choices, and consistent communication, roadblocks can be transformed into stepping stones. Do you need help thinking through an obstacle? Book a free session via my website. I would love to help you!


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