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Join Justin and I for our Workcation to Portland and Astoria, Oregon, and the experiences I had exploring the city's food and coffee scene, natural beauty, and cultural attractions. Along with visits to iconic locations such as Powell's City of Books and the International Rose Test Garden, I also facilitated a leadership webinar and managed a PR crisis for a client while enjoying the flexibility of remote work.

Day 1: Arriving in Portland, The Kimpton RiverPlace and Food

It was a clear, bright morning as Justin and I arrived at the Portland airport, ready to embark on our workcation to the Pacific Northwest. We were both looking forward to exploring Portland's rich food and coffee scene, as well as the city's unique blend of urban and natural environments.

We made our way to the Kimpton RiverPlace Hotel, located in the charming South Waterfront district of Portland, and checked in to our luxurious accommodations. The hotel had an elegant, understated design and a great location right on the Willamette River. Our room was a perfect corner suite that had windows that opened and a beautiful view of the river and bridge.

We got in pretty early, so after getting settled, we decided to grab some breakfast at the hotel's restaurant, King Tide Fish & Shell. I ordered the smoked salmon and cream cheese bagel, while Justin opted for the huevos rancheros with chorizo.

"Wow, this is amazing," I exclaimed as I took a bite of my bagel. "I love how fresh the salmon tastes." Justin nodded in agreement. "This is the perfect way to start our Portland adventure," he said.

With full stomachs, we set off to explore the city, starting with a visit to Coava Coffee in the Central Eastside Industrial District. The coffee shop had a relaxed, industrial atmosphere, with exposed brick walls and large windows letting in plenty of natural light.

"I love how spacious this place is," Justin said as we settled into a table. "And the coffee smells incredible."

As we worked on our laptops, sipping our coffee, we discussed our plans for the week, including a remote workshop we're facilitating for a client on "Working Parents" and the various restaurants and attractions we hoped to visit.

For lunch, we decided to try Lardo in the Hawthorne neighborhood, a local restaurant with a focus on creative sandwiches and dishes. Justin ordered the dirty fries with pork, while I went for the BBQ pork sandwich.

"These fries are insane," I said as I took a bite of his crispy, flavorful dish. Justin nodded in agreement. "I'm really impressed with the quality of the food here. It's obvious that they take their ingredients seriously."

After lunch, we decided to visit the International Rose Test Garden, located in Washington Park. The garden was home to over 10,000 rose bushes and outdoor exhibits, making it a beautiful and peaceful oasis in the heart of the city.

As we walked through the garden, taking in the vibrant colors and fragrant scents, we discussed the challenges and opportunities of remote work, sharing tips and advice with each other.

As the sun began to set, we headed to Ox in the Concordia neighborhood for dinner. The restaurant had a cozy, rustic atmosphere, with an open kitchen and a focus on Argentine-inspired cuisine and wood-fired meats.

We ordered a variety of dishes to share, including the grilled octopus, the beef short ribs, and the grilled broccolini. Each dish was beautifully presented and bursting with flavor, and we savored every bite.

"I can't believe how good this food is," I said, taking a sip of my cocktail. "I'm so glad we decided to come here."

After dinner, we headed to Teardrop Cocktail Lounge in the Pearl District for a nightcap. The bar had a sophisticated, upscale atmosphere and an impressive cocktail menu, and we enjoyed sipping our drinks while chatting about our day.

"This is the perfect end to a great day," Justin said, raising his glass. "I couldn't agree more," I replied, clinking my glass against his.

Day 2: Working Remotely, Exploring Portland and Learning

The next morning we woke up early and decided to start our day with a visit to Barista in the Pearl District, a local coffee shop with plenty of workspace and great coffee.

"I love how cozy this place is," Justin said as we sipped our coffee. "And it's great to have a change of scenery from our hotel room."

After finishing up an eBook for an HR Tech client, we decided to try Nong's Khao Man Gai in the Central Eastside Industrial District for lunch. The local food cart had a focus on Thai-inspired chicken and rice dishes, and we both opted for the classic Khao Man Gai dish.

After lunch, we visited Powell's City of Books, one of the largest independent bookstores in the world. The bookstore had a sprawling, labyrinthine layout and was filled with books on every subject imaginable.

"I could spend hours in here, and I can't wait until I can find my book, 'F*ck Your Office Snacks, on these shelves. Justin smiled. We spent the afternoon perusing the different sections of the bookstore, finding new books to add to our reading lists and chatting about our favorite authors.

For dinner, we decided to try Ava Gene's in the Division neighborhood, a local restaurant with a focus on Italian-inspired cuisine and seasonal ingredients. The restaurant had a cozy and romantic atmosphere, and we enjoyed the warm lighting and the intimate seating. We started with the antipasti platter, which included a variety of cured meats, cheeses, and pickled vegetables, and then moved on to the main course. I ordered the spaghetti alla chitarra with crab, while Justin opted for the pork chop with roasted peaches.

As we sipped our wine and savored our meal, we talked about the leadership lessons we'd learned over the years, sharing stories of our successes and failures.

"Leadership is about being willing to take risks and make tough decisions," I said. "But it's also about being willing to admit when you're wrong and make amends." Justin nodded in agreement. "And it's about leading by example and setting a positive tone for your team," he added.

We ended the night with cocktails at Rum Club in the Buckman neighborhood, a local bar with a tropical-inspired atmosphere and great drinks.

As we walked back to our hotel, we both felt grateful for the opportunity to explore Portland and deepen our friendship and partnership at the same time.

Day 3: Driving to Tillamook, PR Crisis and the Sea Lions Astoria

We started our morning at Upper Left Roasters in the Pearl District, enjoying a delicious cup of coffee and discussing our plans for the day ahead.

After finishing up our emails, we hit the road towards Tillamook Cheese Factory to sample some of the best cheese in Oregon. We were excited to see what this famous factory had to offer and couldn't wait to try some of their local delicacies. As we drove along, we marveled at the beautiful Oregon scenery, with rolling hills and lush forests stretching out as far as the eye could see.

Upon arriving at the Tillamook Cheese Factory, we were greeted by a wide range of cheese samples to taste, as well as other local goodies like ice cream and fresh fudge. We also took their self-guided tour to learn more about the history of the factory and how the cheese is made. We couldn't resist buying a few things to bring back home as souvenirs, including some of their famous cheese curds.

Next, we made our way to Cannon Beach, where we saw the famous Haystack Rock and took a quick stroll along the beach despite the typical Portland weather of rain and cold. After our stop at Cannon Beach, we headed north towards Astoria, with the rain coming down in sheets as we made our way along the winding coastal road. Along the way, we stopped at a local bar to warm up with a hot toddy and were surprised to find a unique Oregon Lottery run slot machine that had us both cheering and laughing as we won big.

As we made our way into Astoria, we were blown away by the stunning views of the river and the town's charming Victorian architecture. We arrived at the Bowline Hotel and were immediately impressed by the property's location right on the river and the sounds of the sea lions that could be heard from our riverfront balcony.

After settling into our room, I took a call from a client who was experiencing a PR crisis. With my years of experience in crisis management, I was able to quickly assess the situation and propose a strategy to help the client navigate the situation. I was grateful to have the flexibility of working remotely, as it allowed me to help my client while also enjoying the beauty and relaxation of Astoria.

That evening, we headed to the hotel's restaurant to sample their delicious locally sourced cuisine, which did not disappoint. We marveled at the incredible flavors and savored every bite as we looked out at the stunning views of the dark river.

After dinner, we took a steam in one of the hotels Barrel Sauna's. It was awesome and just the right amount of detox to have a fresh start to the next day.

As the night wore on, we curled up in our bed and we drifted off to sleep, dreaming of the adventures that awaited us the next day, which included exploring Astoria's charming downtown and visiting local wineries as we made our way back to Portland.

Day 4: Back to Portland, Webinars and "Jock Strap Night" at The Eagle

After finishing up some emails, we spent the morning facilitating a leadership webinar focused on introspection and learning. We talked about the importance of taking the time to reflect on one's experiences, behaviors, and beliefs, and how doing so can lead to personal growth and development. We shared techniques and strategies for practicing introspection, such as journaling, meditation, and seeking feedback from others.

We also discussed the power of vulnerability and how being willing to be vulnerable with others can build trust and create deeper connections. We shared examples of how vulnerability can be expressed in the workplace and the positive outcomes it can lead to, such as increased collaboration and problem-solving.

Our participants were engaged and shared their own experiences and insights, making for a lively and thought-provoking discussion. We wrapped up the webinar feeling energized and excited to see how our attendees would apply the concepts we discussed in their own lives and work.

Once done, we packed up and checked out of the Bowline Hotel. But before heading back to Portland, we took some time to explore Astoria.

Our first stop was the iconic Goonies House, where we took some photos and reminisced about the classic movie. From there, we headed downtown to check out some of the local shops and grab some coffee from the charming Astoria Coffeehouse & Bistro.

Next, we made our way to Buoy Beer, a local brewery with a stunning waterfront location. We enjoyed a tasting flight of their delicious beers, including their flagship IPA and a seasonal sour.

We made sure to stop by the Columbia River Maritime Museum to learn about the history of the Columbia River and the brave men and women who have navigated its waters.

As we made our way back to Portland, we stopped at a few wineries along the way, including David Hill Vineyards and Montinore Estate. At David Hill, we tasted their award-winning Pinot Noir and Pinot Gris, and at Montinore Estate, we enjoyed a flight of their biodynamic and organic wines.

Dinner was at Lechon in the Pearl District, a local restaurant with a focus on South American-inspired cuisine and wood-fired meats.

After dinner, we met up with our friend David, who just moved to Portland, for a night of karaoke at the legendary Alibi Tiki Lounge. We all belted out our favorite tunes and even tried our luck on the Oregon Lottery-run slot machines. I ended up winning $180, which we all celebrated with a round of drinks.

As the night carried on, we made our way to The Eagle, a gay bar that David had discovered in his first few weeks in Portland, where it was "Jock Strap Night." While we may have been a bit overdressed, we had a blast and even tried our luck on the Oregon Lottery-run slot machines. I ended up winning $180, which we all celebrated with a round of drinks.

After a night of singing, dancing, and laughing, we checked back into the Kimpton RiverPlace Hotel in Portland, exhausted but exhilarated from our adventure in Astoria.

Day 5: Exploring the Pearl, Visiting Vancouver & Saying Goodbye

It was our last day in Portland, and the sun was shining bright. After grabbing our morning coffee from Heart Coffee Roasters, we walked around downtown Portland, exploring the city and enjoying the beautiful weather. We stopped by Powell's City of Books and picked up a few new reads before heading to the Portland Art Museum.

As we walked through the museum's galleries, Justin and I talked about how much we had learned on this trip, both personally and professionally. We reflected on our leadership webinar and the importance of introspection in growth and development. We also talked about how our network had expanded during the trip, and how we were excited about the potential opportunity to work with the owner of The Eagle.

Justin and I have never met a stranger, and our trip to Portland was no exception. Everywhere we went, we struck up conversations with the people we met, and we left with new connections and potential partnerships. We even met a few locals who were gracious enough to share some of their favorite spots with us.

After a few hours of exploring, it was time to head to Uptown Barrel Room in Vancouver to meet up with my birth mom and her husband for brunch. The food was amazing, and we spent a few hours catching up and enjoying each other's company. We talked about how much we loved the Pacific Northwest and how we hoped to come back soon.

As we dropped off our rental car at SIXT and headed to the Portland airport for our flight back to Austin, Justin and I reflected on what a great trip it had been. We were grateful for the opportunity to combine work and pleasure and explore a new city. We left Portland with new connections, new experiences, and a renewed sense of motivation for our work.

Here are some tips for working remotely and staying accountable to yourself:

  • Set clear goals and prioritize tasks for the day to maintain focus.

  • Take breaks and engage in physical activities to boost energy and productivity.

  • Use apps and tools to stay organized and on track, such as calendars and project management software.

  • Create a designated workspace to signal to your brain that it's time to work and avoid distractions.

  • Communicate with team members regularly to stay accountable and aligned on goals and expectations.

  • Reflect on your work and identify areas for improvement to continue growing as a leader.

  • Embrace the benefits of remote work, such as the flexibility to explore new destinations and cultures, and prioritize self-care to maintain a healthy work-life balance.

Here are some ways to stay accountable to yourself when working remotely from distracting locations:

  • Practice self-awareness and reflection to maintain focus and accountability while working remotely from potentially distracting destinations.

  • Set clear goals and prioritize tasks to stay on track and ensure productivity.

  • Communicate regularly with colleagues and clients to stay connected and engaged in work.

  • Embrace the mental health benefits of remote work by taking advantage of new environments, experiences, and opportunities for personal growth.

  • Lead by example and encourage others to find a healthy work-life balance that supports both productivity and well-being.

  • Recognize and celebrate successes, both personal and professional, to foster motivation and a positive team culture.

  • Be adaptable and open to change, while also maintaining a sense of structure and routine to stay organized and focused.

Where did we Go? What did we Do? Where did we Stay? What did we Eat & Drink?


  • King Tide Fish & Shell (

  • Lardo (

  • Ox (

  • Ava Gene's (

  • Lechon (

  • Buoy Beer (

Coffee Shops:

  • Coava Coffee (

  • Barista (

  • Upper Left Roasters (

  • Heart Coffee Roasters (


  • Teardrop Cocktail Lounge (

  • Rum Club (

  • Alibi Tiki Lounge (


  • Kimpton RiverPlace (

  • Bowline Hotel (


  • International Rose Test Garden (

  • Powell's City of Books (

  • Columbia River Maritime Museum (

  • Goonies House (

  • Portland Art Museum (

  • Tillamook Cheese Factory (

  • David Hill Vineyards (

  • Montinore Estate (

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