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February 15, 2018

When Success Brings You Pain

This post isn’t a how-to guide to alleviating your problems, like some of my other posts. This post exists because I felt it was important to share this moment in my life. To let you know that you’re not alone – that whether you’re just starting out or you’ve been at it for a while, being a creative or entrepreneur can be a challenge emotionally. I hope you enjoy it!


When Success Brings You Pain | seattle stationery and calligraphy


My husband told me, in all seriousness, “I’m going to buy something from your shop so that you can spend some time with me.”

O-U-C-H. Shot to the heart, right?

On the same day, something else equally alarming happened: my work was featured on a major wedding blog, I wrapped up three clients, signed up another for a March wedding, and pulled together some new marketing materials. It was a super productive 24 hours for this little entrepreneur, but I didn’t feel at all productive or accomplished…even more so after what my husband said.

So how do those two things relate to each other?

Well, it was clear that something was very wrong. I realized that I had really been neglecting the most important part of my life (my family) to pursue the entrepreneur life. I looked at my achievements and all I could feel in the pit of my stomach was disappointment. It was an icky feeling and I did not like it. one. bit…and I’m going to come back to that later.

I had been neglecting the most important part of my life


Entrepreneurs got 99 problems…so we all need a break sometimes.

Whether you’re a competitive person by nature or not, you can probably understand how crushing defeat can feel…and how exhilarating a win is. But have you ever felt indifferent about winning or relieved at losing? Chances are that you have. I have, too. From the conversations I’ve had with many of you and the books/blog posts/articles I’ve read about running a business, it’s a pretty normal thing for entrepreneurs.

It’s a dangerous feeling, especially when you have a day like mine: when you succeed at something and you don’t feel elated, or feel like your career is progressing and you kind of shrug it off like, “Meh.”, or your husband says something that rips your heart open. It’s dangerous when you’re too busy getting your hustle on that you miss out on every other part of life, because:

Why do we hustle if we’re not enjoying the fruits of our labor?

And guys: that is downright HARD for a workaholic to admit…and even harder to admit when you love what you do and the hours just fly by.

I couldn't enjoy my successes any longer because I was so focused on the next mountain I had to climb

What are some causes of this?

  1. Comparison: We’re talked about this before, and this has been going on for centuries. It can drain your competitive nature and creativity, but I haven’t met a single person yet who hasn’t compared themselves to others at any point in time. But I’m a firm believer that comparison is a good thing in moderation: it keeps you hungry, it encourages you to think out of the box, and it can keep you from becoming complacent.
  2. Complacency: Sometimes, we’re stuck in a rut and don’t realize it (or maybe we do). Doing the same thing over and over every day can wear you down (and the opposite is not true, I’ve found: constantly surrounding yourself with new experiences and people and ideas and creativity makes you MORE creative, not less so).
  3. Fear: Do you worry you’re not talented enough to succeed? Do you look at your work and see all the flaws and the work that went into getting there, rather than the end product? That’s a happiness-sucker.
  4. Overbooking/Fatigue: There IS such a thing as having too much on your plate. The reason I lumped these two together is because one (overbooking) can often lead to the other (fatigue), which drives down your productivity and happiness levels.

Yeah, yeah…you’ve heard all of this before. I know. But I think it’s important to remind ourselves that these things can get in the way of our happiness. It certainly helped me to think about why I was feeling that way.

And I got to the root of it, alright: I was exhausted. I was working 16+ hour days on my little business and spending next to no time with my family and friends. I’m a workaholic and I really, really enjoy what I do, so it’s hard to pull myself away sometimes. I had started to crawl into bed long after my husband fell asleep, reading up on new techniques and trends in the industry before finally passing out in the wee hours of the morning…only to do it all again the next day.

I was hustling and loving every second of it, until it caught up to me. I couldn’t enjoy my successes any longer because I was so focused on the next mountain I needed to climb. Once I recognized it, I remembered an AMAZING Ted Talk that I actually downloaded to listen to on my iPod (yes, I still have one several of those).

It’s about 12 minutes long, but it’s a great video. I recommend watching it with sound, but the captions are there just in case you can’t.


What happened next?

Well, after I stopped myself crying, I shut down my office and went to cuddle with my husband. It made us both feel better.

Since then, I started spending more time doing non-business activities. I actually suggest going to the movies and taking mini shopping trips (the horror!). My friend Katie took me to an actual art museum and then we went impromptu antiquing for a WHOLE DAY, and the world didn’t fall down around me. I woke up the next morning refreshed, and finished ALL my work and even get started on fresh projects for my business (that almost never happens). I made myself go to networking meetings and actually enjoy them now (remember the “trying to get out of saying my vows in front of people” bit I mentioned earlier? Talking in front of people isn’t my favorite activity, but it gets easier with practice!).

Taking (and making) time saved my sanity. I don’t know what the magic amount of free time versus work time is, but I do know that I need more off time than I was getting before. Now, I can celebrate wins (and actually enjoy them), participate in conversations when I’m with my husband or friends or meeting new people, and even have time to learn a thing or two.

And if you haven’t really celebrated a win in a while – if you don’t do an embarrassing little dance when a client approved their proof or pays their retainer – do it now. Blast the music, do a little jig in your seat, and then figure out how you can do that more often. We as entrepreneurs have to remember that we’re human beings first and workers second.

Good luck, lovelies!


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  1. Thank you for sharing this post, I think it’s really well written. Although I don’t have my own business yet I do compare my handmade cards to others on social media. It’s very easy to get wrapped up in it all isn’t it. I wish you all the best for your business & hope you find the balance that works for & your family

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