When Changing Your Business Is Harder Than Starting It

Tara here. I know many of you are just starting on this adventure of building a business and brand of your own. Welcome to the wild ride! Some of you are starting on a career path working within an organization (it may not feel as wild as going rogue, but you’re still carving out your way!) Hello to you, too.

But! I’m not talking to the “just starting outers” right this moment. Nope. I’m talking to the “been-around-the-blockers.” You are at a fork, a bend, a crossing, or you simply want to stop going around this same block and try some new territory. You aren’t just starting out on this journey – you are transitioning your business or your expertise into “what’s next” for you.

And for some reason, this transition can feel a lot less exciting than the early days of starting something completely new, and frankly, more daunting.

Why does transitioning our business, our brand, or simply our expertise feel harder than starting from scratch? It’s not. We just forget how hard it was in the beginning.

When we remember the excitement of those first days, everything—even when it was small—felt big: “The first client! The first dollar! The website finally launching! The product growing! The first hire! This is working! This is sustaining! This is exceeding what I imagined!”

In retrospect, the not-so-exciting, awkward, or stressful stuff somehow seem minimized. Those early trial and error days at worst are remembered like well-earned war stories, and at best seem almost cutely naive: “Remember when I took on that project that was completely bonkers? Remember when I hosted that workshop and only ten people came? Remember when I thought my specialty was going to be A., but it turned out to be Z? Silly me! Those were the days, ha ha ha. Sigh.”

So when we look forward to what’s next for us, why do we all of the sudden become so unforgiving of any trial and error, completely annoyed by any awkwardness at all, and somehow no longer interested in the fun parts? Why is the dreaming part replaced with grim determination? Is it because we know too much? The problem is, knowing better doesn’t necessarily feel better.

Shifting direction in your business

Maybe you’re different. Perhaps you love a really earth-shattering evolution. You don’t mind being out of your depth again. When I try something completely new for my career or business, I tend to feel like an anxious sixth grader starting middle school, and all my fifth grade rule-the-school swagger is totally knocked off center.

You’re smarter and more experienced than when you started out – but that doesn’t always equate to feeling more confident when you’re in transition. It’s hard going back to feeling like the new kid on the block.

Feeling like you're starting over when making changes in business

Here are some of the goals we hear all the time (and have tackled ourselves) that get us into this transition in the first place – and then later get us asking “What did I do!? Why didn’t I leave well enough alone!?”

  • I want to scale.
  • I want to take this one-on-one service online.
  • I want passive income.
  • I want to build a team.
  • I want to reach a completely different dream client than I have been.
  • I want to package up my offering so it doesn’t read like a menu!
  • I want to stop being compensated for just my hours and instead get compensated for my expertise.
  • Last, this is a big one: I want to transition into a completely different specialty or career path! (That one doesn’t count, because it really IS as exciting as starting over!)

The transition to each of these milestones isn’t always fun. But, guess what, it’s worth it once you get there! So I want to give you a few reminders to help you remember to, well, at least TRY to have fun along the way, to get excited again, and to feel like this leg of your journey is just as fresh as the first time around:

    • Remember your voice! don’t go changing your whole style just because you’re growing.


    • Remember what you are best at! Don’t start spreading yourself thin or selling yourself as a Jane of all trades just because you’re “expanding.”


    • Remember what you are worth! Don’t start underselling yourself just because you feel like you’re starting over or specializing to a different niche.


    • Ask: What am I taking for granted? It could be a creative talent or a flair for presenting. Don’t throw out the talented baby with the bathwater of your old package or offering!


    • Ask: What is my dream client missing that I’m not giving them already? Could be it’s right under your nose, and it’s not as complicated as you think – it could be they need confidence from you, understanding from you, tough advice from you, or some usable, legit know-how from you!


  • Ask: How can I keep this dreamy for me? What aspect of this evolution can you really own because it’s your total wheelhouse, it’s your jam, it’s your dream work? What can you then hire someone to help you with? Often when we grow or transition we have to ask for help where we never have before. Some of us aren’t used to partnering, contracting out, hiring or asking for help. But oh, man, it’s the best!

We love helping creative entrepreneurs package themselves more clearly, to feel purpose-fueled and professional (yup, at the same time!) and blend who they are into what they do. If you’re a solopreneur, sign up for our Letters for Creatives in the sidebar.

We’ve also just launched a new offering for you creatives, marketing and communications specialists who are working within organizations. Check out BraidCreative.com/TeamVisioning for ideas on how you can reinspire and reframe what’s next for your team. While you’re at it you can sign up for our Branding & Marketing Letters for Businesses, where we’ll bring you fresh perspectives from out in the creative entrepreneur world as well as our own advertising agency experience (but also maybe… gasp!… some fun and personality!) into the work you do together.



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