I split my time between Chicago (where I work) and Los Angeles (where my husband works). “How does that happen?” you wonder. 
Around three years ago I was looking for a new challenge in my career. After months of researching what I was looking for next — via countless interviews, informational meetings and coffee catch ups — I found the perfect next job, but it was at a different company. As much as I wanted the role, I knew it would add a lot of value to our organization. So I took the job description to my CEO and made the pitch to create that role at our company. It was a big ask, but he was on board. 
A month later, as I was still basking in the glow of my success negotiating my new job, my husband was offered a job at his dream company. Only problem? It was in California. I wasn't ready to give up the position I had just built, and he wanted to take a chance with this amazing opportunity. We were determined to find a solution that would allow us to have the careers we wanted without sacrificing the marriage we wanted. 

Finding the Elusive Win-Win  

We decided keeping apartments in both cities and traveling back and forth would offer more stability (for us and our companies) than traditional consulting-style travel where you’re gone during the week and return home for weekends. 
Each job came with a raise, so we could handle rent for a second place and still hit our savings goals. All we had to do was see if our companies would allow it. 

How to Make the Ask to Go Remote 

For us, remote work was a non-negotiable — if either company wouldn’t allow it, my husband wasn’t going to take the new job.  
If you’re negotiating a new job, bring up remote work early when discussing benefits. Companies might say they’re open to it, but get specifics: When can you start working remotely? How many days can you be out of the office? What training or meetings do you need to attend as you start your job? 
At your current job, set up some time to talk to your boss and then discuss the following: 
  • Determine if it’s possible. Remote work is more common than ever, and certain industries (I’m in tech) can accommodate it. That said, large companies or more traditional industries might not. 
  • Explain the situation. Life happens, and families move for jobs. Be clear about how this decision is larger than just you. The most important thing for my boss was hearing that I was excited about my role and did not want to leave it.  
  • Assure them your work won’t be affected. My new job was my priority, and I had no intention of dropping it when I settled in California. I proved this by showing which meetings I’d return to Chicago for and scheduling check-ins the first couple months to discuss improvements. 
Some companies will pay for minor expenses, like a second computer, and some will cover your flights or even a hotel when you are in town. Unless your boss brings it up, keep this out of the initial conversation about working remotely. Focus on one ask at a time.  
Fresh out of college? Just trying to explore the world? Been at your company for less than a year? Lower your expectations. This is a big ask. 

How We Make It Work 

After nearly three years, we’ve got our LA-Chicago lifestyle down. Here are our pro tips if you’re thinking of doing something similar. 
Plan at least six months out. I account for holidays, family events and work meetings in an enormous Excel spreadsheet. I plot our travel to get the timing just right. Beyond fitting in commitments, locking in dates early can be the difference between a $200 or $500 ticket. 
Become loyal to an airline. Status is a game changer. You get better seats, more perks and free miles. We even have an airline credit card where racking up points equals free flights.   
Set a routine. If I take the same flights, I know how much time I need to eat, close up the apartment and get to the airport. Similarly, I sit in the same row on the plane and have designated travel-day outfits. 
Buy two of the things you like. After years of shuffling my favorite shoes or jeans back and forth, I ended the madness and just bought second pairs. Quality of life dramatically improved when I wasn’t lugging a 40-pound suitcase every two weeks. 
Get a good tax professional. We’ve got two states to file in, company stock vesting, my writing side gig, electric car credits, home office deductions ... it gets messy. We found a tax professional that has several clients with the same lifestyle.  
Take care of yourself. Staying healthy is a must. I try to eat well, exercise and never skip doctor’s appointments. Saying “no” to friends and family is the hardest part of our career choice, but in our first year we tried to keep our old social calendar and we both got sick.  
Have an exit strategy. We went into this adventure saying we would commit for one year. Every six months, we sit down to evaluate our finances, our leases, our career goals and how much longer we want to keep it going. We need light at the end of the tunnel.