Deciding to do something that strays too far from salaries and time clocks can be scary. Even a terrible soul-sucking job has the certainty of a paycheck, so getting to the place where you’re confident that you can go out on your own is a huge personal step. The part that often comes as a surprise is that your friends and family don’t necessarily jump for joy when they hear the big news.

When I decided to open Tog Loft I wasn’t leaving a great job, I’d been self-employed for over a year.  I’d done months of research and I had a business plan that managed the risks pretty well. In my estimation I had more to gain than lose so it never occurred to me that my family and friends would be anything but supportive. I knew that other people often struggled to get the support of their family and friends, but my family and friends, they weren’t like those people…..or were they?

Turns out that a few people were pretty vocal about how much they opposed the idea, and it stung. Actually that’s putting it lightly, it felt like an existential crisis. How could people I loved fail me in such a deeply personal way? I was hurt, angry, and unprepared to deal with the opposition.

So I turned to Google, which directed me to a variety of pieces of advice on a spectrum from bad to horrific. Next I dumped my problem on strangers in a Facebook group for women entrepreneurs, and there I got mixed, but slightly more thoughtful advice. In the end I had to go with my gut, because really, I was just looking for outside confirmation anyway. I’d already done the work, I knew where my heart and mind were, and I had to go with that and find a way to bring the others along, or defy them.

There are a variety of reasons why people will throw up roadblocks to your dream. The reasons fall into some “archetypes” if you will, so I’ve named the naysayers and picked apart their agendas and motivations.

Worker Bees

Some people derive real joy and comfort from a good steady job. The truth is that there are lots of perks beyond the steady paycheck, and worker bees are happy where they are.  So happy in fact they can’t understand why you’d want to do anything else.

Failed Entrepreneurs

No matter which set of statistics you look at, the commonality is that the majority of new businesses fail. Regardless of the reasons for that, the one key takeaway to remember is that you likely know a handful of people who experienced that failure. Some of those failed entrepreneurs plug away and push through that failure and keep at it until they succeed, but a lot of others take it as defeat and retreat to another career path.  Those that failed and retreated are very likely to rain on your parade because they’re hoping to spare you their fate, or they’re just bitter and negative, either way it really doesn’t occur to them that you could have a different ending to your story.

Joyless Vampires

Some people are really unhappy and prefer to ensure that those around them are also unhappy. These vampires make it their mission to suck joy out of anyone who might dare be happy in their presence. Follow your passion and do something that makes you happy and you can be certain that someone will try to drain you of joy before that sunshine happens to spill into their dark little heart.

Nervous Nellies

Worry is a funny thing, a small amount of it keeps us from doing truly stupid things, but in excessive quantities it can be paralyzing. In fact, lets call a spade a spade, worry is just a nice word for fear. Change in any form is prime cause to set a worrier to fretting, and worst of all, meddling.

Green Eyed Monsters

Some people fully understand what you’re doing, but they don’t have the guts to do it themselves and they’re jealous. It’s simply easier to discourage you than muster up the courage to do it themselves.


Notice anything about all these characters? In each and every case it really comes back to them, their issues. If someone isn’t supportive or encouraging, their actions, words, and behaviors are all about them, not you. It hurts, but the trick is to acknowledge it for what it is. On some level the people who care about you believe they’re “helping” and aren’t self-aware enough to realize that they’re dumping their issues onto you.

When I had to face my detractors the words of another entrepreneur kept going through my head. I had asked Paul Smith, who owns a local wine bar called the Happy Grape, about his path to entrepreneurship. I had wondered how his friends and family had reacted when he told them his plans.

“Some people thought it was a great idea,” said Paul, “Others thought it was the stupidest thing we could possibly do.”

“How did you know who to listen to?” I asked.

“Neither,” he said. “You listen to yourself, and I knew I could do this.”

Ultimately that is what I decided. I knew I could do this, and that’s what mattered. I had to summon up the gumption to say, “You can be with me or against me, but either way, this is what I’m doing.”

I suppose there is more than one way to say it, but the sentiment most likely is the same. In the end you have to choose yourself.  Your dream, your life, your business. Life is too short to be lived for anyone else.