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It Doesn’t Always Work Out

black heart

If there’s one thing I’ve learned over the last 18 months of entrepreneurship, it’s that I have a head of steel and a heart of mush. I have no problem making important decisions when it comes to business, and can handle conflict like a champ. But when it comes to the more personal side of things, including relationship issues, family matters, and healthy criticism, I find that my head stops working and my heart takes control. That soft spot that I don’t like to reveal comes out. I get defensive, sad, frustrated. It sucks.

Last year, I won the business of a client I had only read about, but never thought would hire someone like me. I was excited, nervous, and unsure about the decision to take this client on because they had negotiated a retainer that was less than my normal rates. It was clear that this client was a workaholic, someone who was up before dawn type-type-typing away until midnight, getting a few hours of shut-eye, and then starting it all over again. Are the warning bells going off in your head? They went off in mine, but I chose to ignore them, hoping the prestige of the client’s name would help me get more clients in the future. Assuming it all worked out, of course.

Well, it didn’t. The constant flow of convoluted information, misunderstanding of expectations, and most importantly, a lack of perceived value in the services I was attempting to provide left us both with a sour taste in our mouths and a cutting of ties just 6 weeks into the relationship.

I learned a lot from the initial shock of this experience. Most importantly:

Don’t have important business conversations at a conference. You might cry in front of strangers.


But back to the point: This isn’t a story about failure. I recognize that my company offers something that’s not for everyone. It takes a certain type of leader, a certain communication style, and a mutual understanding that both parties need to invest some serious time and energy into finding a flow that works before you truly start to see the value, and that that value can be extremely important in the growth of your business. But when things weren’t working out and I was being forced to track every minute of my time, even down to details like email responses, I felt personally attacked. Why wasn’t this working? What was I doing wrong? Why does this client hate me so much?

I had never experienced such a neurotic, always-on, micro-managerial client before, and I didn’t know how to handle it. I beat myself up for days, even weeks after our relationship ended, trying to figure out what I could have done to change the outcome.

One day, after talking to a close friend about the situation and trying to keep a steady voice and a level head throughout the conversation (even though I felt like sobbing in her ear), she made me realize that it doesn’t matter if I was right or the client was right. We both thought the other was the issue. We both thought we did all we could. And that was okay. It can’t always work out. Flying high on the waves of success for so long made me forget this important reminder. And an opportunity for personal growth was on the rise, some lessons that I could apply to my business procedures (or lack thereof) that would have great importance in the success of my reputation, my business, and my fragile heart:

  1. Don’t let email be the place to have important and sensitive conversations – Tone is not clear in emails. Don’t let important decisions be made in an email trail, and don’t let clients get away with never wanting to get on the phone. I hate the phone just as much as anyone, but sometimes it’s impossible to explain expectations and goals in an email. That vocal layer of communication is important.
  2. Ask for feedback after the first 30 days – In this case, feedback can be in the form of an email or a phone call. I know that for me, email can be easier because it allows me to organize my thoughts and think about how to deliver them more effectively. It also leaves a paper trail of information in case you need to reference back to it in the future. This goes for personal relationships too, not just business relationships. You can subtly take the temperature of a personal situation without calling it “gathering feedback”. 
  3. Schedule standing calls, even if you don’t actually stick to having them every time – For new clients especially, I always try to schedule weekly calls. We don’t always have them as long as things are on track, but it’s good to touch base via phone in a virtual business at least once a month, if for no other reason than to shoot the shit and remember why you love working together.
  4. Request ongoing feedback – I know I’m not the best at this, since I usually get and give feedback on the fly, but I’m working on putting together a quarterly client survey so we can make sure we’re always growing and adjusting to our clients’ expectations. 
  5. Make your love for your clients clear – I sent some Don’t Panic swag to clients around the holidays. It was somewhat silly, but well-received. I also try to thank clients via email, Twitter, and Facebook whenever I can, send them birthday presents, and am working on writing LinkedIn recommendations. Small thoughtful acts of love go a long way, especially in a virtual business relationship. 
  6. Listen to your gut (or my case, your mushy heart) – I know we’ve all heard this before, but it’s really important and is worth saying again. I knew in my heart that working with this client wasn’t a good idea, but I didn’t spend enough listening to myself to really understand it. I often have this problem, and am working on getting better at it. Pro/con lists help in this case, as they often reveal the standpoint of the heart in a more practical and tactical way.

It sucks when things don’t work out, and I’ll admit that I still get disappointed on a pretty regular basis (man, does my heart need to do some pushups, what a softie). But putting some new benchmarks and processes in place has helped me feel more confident that I really did do everything I could and that if it doesn’t work, then it just wasn’t meant to be. And there’s no use crying over spilled client guts. I mean, milk! Spilled milk! ;)

  • schmittastic says:

    ALL THE THINGS in common with you right now! OMG. I am so sorry one of your work relationships didn’t work out. SO hard to analyze whether you failed or you just didn’t fit together when you’re so distraught like I have been in these situations. I love the idea of the survey and regular calls are so necessary. You know exactly what to do, girl and that’s why you’re so brilliant at it with your existing clientele. Some people with stellar reputations are just good with smoke and mirrors. No hate to your ex-client, but they, like me, just need to figure out how to ask for help and then allow it to happen.

    February 15, 2013 at 1:40 pm
  • JesseBouman says:

    Great advice. I’m terrible at #5.

    February 15, 2013 at 1:56 pm
    • jess says:

      It’s hard to remember to love, especially for men :) This is just a reminder!

      February 15, 2013 at 5:14 pm
  • badonlinedates says:

    Good stuff Jess. I will say that my own “mushy heart” has been perhaps the best quality that I have. Countless tears later – it has forced me to really listen and to pay attention to all levels of life. Both the good and bad. xoxo

    February 15, 2013 at 2:17 pm
    • jess says:

      I totally agree with you! Sometimes it’s better to be overly sensitive because it makes your eyes and heart open to new opportunities. Thank you.

      February 15, 2013 at 5:16 pm
  • kateupdates says:

    LOVED reading this. Thanks so much for sharing. I just  went into business January 15th and I’m learning a lot fast. Great tips and I will definitely keep Don’t Panic in mind.

    February 15, 2013 at 3:19 pm
    • jess says:

      Oh, how exciting!! Wishing you the best and happy to help any way I can! Thank you for reading!

      February 15, 2013 at 5:16 pm
  • kateupdates says:

    LOVED reading this. Thanks so much for sharing. I just  went into business January 15th and I’m learning a lot fast. Great tips and I will definitely keep Don’t Panic in mind.

    February 15, 2013 at 3:19 pm
  • Michael Guill says:

    Thank you for this. I know I’ve personally struggled with this same type of situation, and it’s nice to read such collected reflection on what exactly happened. You’re helping so many people out by posting something this candidly, and reminding those of us who have been through it before to recognize the signs and make the right decisions. :)

    February 15, 2013 at 3:46 pm
    • jess says:

      Wow, this is the most wonderful comment. Thank you! It felt good getting it out, but even better knowing it can help someone else. Thank you, thank you!

      February 15, 2013 at 5:45 pm
  • DJ Waldow says:

    You are the best, Jess. Thanks so much for sharing your story – so candidly – as well as your suggestions. As you know, I’m about 18 months in as well and have had a similar client experience (wonder if it was the same client – ha! … but seriously).

    I’m most intrigued by #2 above. If there is one thing I’ve learned about myself in the past (almost) 37 years on this planet is that I need – check that – I REQUIRE feedback. Good, back, indifferent … I need to know where someone stands. So I’m curious, how do you go about getting that feedback from a client? Do you email or do you pick up the phone? Do you just come right out and say, “how are things going? are you happy with the work i’m doing so far?”

    Would love to hear your thoughts on this, Jess. Thanks for being awesome.

    February 18, 2013 at 2:32 am
    • jess says:

      Hi DJ :) I usually forget to do it, especially people I’ve known or have worked with for a while, but I’m building it into the new client process (this is literally a document that includes onboarding and monthly processes for the first year).

      Sometimes I don’t need to ask because clients just come out with it on their own, but if you’re feeling like you don’t know where someone stands with regard to your work, then I think that’s a problem that needs to be addressed by you. It doesn’t require a phone call necessarily, although if you’re doing those weekly or bi-weekly checkins then it’s something you could bring up on those, but it could just be a quick email with a few specific questions for the client. Not “how am I doing?” because it’s just too broad. I would ask for one thing they’re happy about and one thing they’d like to see improve/change (at least). No pressure, just when they have a chance kind of thing. I think most people welcome the opportunity to give feedback because it makes them feel like you really care about what they’re saying. My other thought with ongoing feedback is that it gives you an opportunity to ask for things like referrals, testimonials, or LinkedIn recommendations if they’re really happy. Some people draft up testimonials and ask permission from the client, but it’s so much better if they come directly from the client’s mouth (or inbox).

      I hope that helps a little! Thank YOU for being awesome!

      February 18, 2013 at 11:14 am

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