Work-At-Home Success Experts: How to Tackle Obstacles On Your Way To Working From Home


The journey to working from home is an exciting one. It usually starts with excitement and enthusiasm, until something doesn’t go as planned. We asked experts to recount how they tackled obstacles that they faced as they grew their home-based career. Here are their tips and advice for dealing with fears, frustrations, failures and challenges.

 Catherine Wood

Unbounded Potential .


1. One obstacle I faced when I started working at home was creating connection outside of my home so that I didn’t feel lonely. Whether following the advice from Never Eat Alone (Keith Ferrazzi) by scheduling lunch dates, booking personal trainer sessions, or signing up for workout class, I put events in my calendar so I have to go. I take out loopholes and create these external accountability structures so that I’m not just accountable to me.

2. When you work at home, you can either work all the time or never work. What’s been really important for me is setting myself up to win. This means honoring the fact that I’m more efficient in the morning and scheduling most of my clients and meetings before noon. It also means delighting in having my own schedule and being able to create it versus being the relentless workhorse that I default to being.

Melissa Caldwell


The first obstacle that you will face starting out as a work-at-home professional will be, of course, finding that first paying gig. It’s not as easy as simply making your mind up to work from home, you have to have actual work to do from home. My suggestion is to start off small-take one time paying gigs to get word of mouth going, look to websites (such as this one) to find those companies that are offering up jobs. Offer your services up on social media, and network. People can’t find you if you aren’t visible.

One of the most important things that I had to overcome was my lack of proper organization. Setting time to get to work and get it down is super important to the success of your business. Keeping a calendar (or even an app on your phone) will help you to prioritize and complete everything that you need to do for any given day.

Rachel Jordan

929 Marketing 

1. *Start your day at the gym*- For me, heading to the gym first thing in the morning is the only thing that gets me mentally ready to truly seize my day. When I head straight from the coffeemaker in the kitchen to the desk in the home office, I’m not focused. I waste time futzing around, I lack the energy and focus to do my best work.
2. *Think before you work* – Spend at least ten or fifteen minutes thinking about what you want to accomplish today and why. That second part is so important. Some people like to write their ‘big goal’ every day. If that works for you, great. Or if you just have a why for the day, that’s great, too. The important thing
is to have your vision for the day and *only *do the most important things to meet that vision.
3. *Change it up* – Sometimes, you need a change of place. If you don’t feel like you’re finding your flow, get out of the house. Whether you need to head out to the local coffeeshop, the library, or your coworking space, just go somewhere. A change of environment can often unlock the creative thinking you need to find your flow.

Note from Leslie

For me, working at home is an ongoing roller coaster ride. There are tremendous highs and confidence sucking lows. I have learned to deal with the ups and downs of working at home by viewing each challenge or failure in a new light, such as:

  • What can I learn from this challenge. Every time something doesn’t go as planned, I study what happened to see what I can learn from it. Nearly always, I’ll discover something I can do different to turn things around. And once I’m done, I’m more knowledgeable than I was before.
  • It’s an adventure. I often look at my working as a great adventure filled with puzzles and mysteries I need to solve.
  • What doesn’t kill me makes me stronger. While working at home doesn’t usually involve life or death, it can kill your dreams and goals if things go wrong and you give up. Instead, when things go wrong, I fight, and I come out the other end stronger. In fact, I’m convinced that the more you struggle, the sweeter the results and the more you’ll appreciate your success.

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