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Ask Ashley: Is It Always Going to Be This Hard?

I thought that as my business grew and I got more experienced things would be easier. But they aren't. Is it always going to be this hard?

Ashley Janssen
Ashley Janssen
5 min read
Ask Ashley: Is It Always Going to Be This Hard?
Photo by Wil Stewart on Unsplash

Welcome to the Ask Ashley advice column! On the second Wednesday of every month, I answer a question from my subscribers, consulting clients, or social media followers on their biggest productivity challenges.

Have a question you want to submit for another edition of Ask Ashley? Shoot me an email. Questions will be anonymized and may be edited for clarity.


Dear Ashley,

I thought that as my business grew and I got more experienced things would be easier. I keep waiting to see the light at the end of the tunnel but I feel like no matter how hard I work, it’s never enough and I never feel like I quite know what I am doing. Is it always going to be this hard?

- Waiting to See the Light

Dear Waiting to See the Light,

Is it always going to be this hard? No...but also yes…let me explain:

When you first start your entrepreneurial journey, everything is hard. Everything is new and you have to learn so much of the business side of the business, while still doing the thing you set out to do. With each project or sale, you get a little more experience and knowledge. With time, repetition, feedback, and reflection, you learn and get better. Things get easier.

But then they get hard again, which is normal and a good thing...I promise.

They get hard again because your goalposts have moved. To follow the tunnel metaphor, you reached the light, but there is another one further down the tunnel. As you achieve your goals and learn new skills, there are new challenges that come with growth and change.

The things that are hard today are not the things that will be hard next year. The things that are hard today get easier, but then there will be new things that are hard. Part of entrepreneurship is that if you’re doing well, then there will always be new, hard things.

In part, how hard things feel will also ebb and flow with the rhythms of your life, energy, and motivation. As you enter new life stages, the things that worked for you before will not work for you now. Similarly, as your business hits new growth stages, the things that worked before, will not work for you now.

Helpful but not helpful, right? None of this makes you feel closer to the light now.

Here are some strategies to better manage the ebbs and flows and slow things down a bit.

Photo by Mehrnaz Taghavishavazi on Unsplash

1. Make some space in your calendar

When your calendar of commitments gets out of control, it’s hard not to feel like you are on a hamster wheel, running as hard as you can, but not getting any closer to that light. Meetings, project deadlines, kid’s activities, volunteer commitments, business events...the list becomes endless.

Review your calendar for the next 4-6 weeks and for each commitment you have booked, ask yourself:

  1. Is this important to me or my business?
  2. Can it be moved back a week or two?
  3. Can I uncommit from this?
  4. Can I ask for help or delegate this?

Some things will need to stay as they are, others will have wiggle room to be adjusted. Make some space.

This might bring up some anxiety if you are a people-pleaser and are worried you will lose out on money, connections, or have someone not like you. Take a read of my article on fear-based decision-making. One way I mention to manage that anxiety is to flip the script: ask yourself, if someone sent you an email asking you to push a meeting back or said they couldn’t make it to your event, how would you react? You are probably fine with it!

2. Set realistic expectations by time-blocking your ideal week

One of the big challenges I see with many of my consulting clients is they completely overestimate what they can get done each day and week. A way you can reset your expectations and get a more realistic view of how much time you have available is by planning your ideal week. You can read the whole article with instructions, but the gist is:

  1. Map your ideal standard week. This is everything you normally do each week. Normal routines like wake up, eating, commuting, bedtime, recurring meetings, recurring kids activities etc. PLUS things you want to do like fitness, time with your partner or friends, focussed creative time, etc.
  2. Map your actual week over top. This is your current calendar of commitments.
  3. Look at the gaps. You will get a visual of what you want to be doing, versus what you are ACTUALLY doing.

I suspect you will be surprised by how little ACTUAL available time you have each day and week. Now you can time block your tasks into the gaps a more realistic way.

3. Get get clear on your priorities

Once you have a bit of space and more clarity on how you are spending your time versus how you want to spend your time, think about what’s important to you. There will always be more work, but time is finite.

Your priorities will constantly be shifting between your business, family, friends, and whatever else is important to you, and that’s ok. Problems pop up when your priorities get stuck on one aspect of your life.

Set audacious goals and be ambitious. But be conscious of the cost. Make sure it is not at the expense of your health or relationships, and that you are actually motivated by your goals. Your business is important, but so are the other things in your life that make it full and vibrant.

4. Protect time for your most important asset...you

You are the most important asset in your business and life. When you run yourself ragged you are doing a disservice to you, your business, and all the other priorities in your life. It’s a competitive advantage to make self-care a priority, but you have to build it into every day and every week. What recharges you? What fills you up? Whatever it is, book the time in your calendar, make it part of your routines, and DO IT.

Photo by Susann Schuster on Unsplash

5. Seek help and support

As you move forward in your entrepreneurial journey and come across new challenges, it’s powerful to talk to other entrepreneurs who have already been there. Look for other entrepreneur communities that you can be a part of to ask questions when you need help. There are tons of Slack channels, forums and meetup groups depending on your business and the type of support you are looking for.

Beyond that, consider if a coach or consultant would be valuable (shameless self-plug!) to help you work through some of these processes if you are not confident you can do them on your own. They will help you set a plan and keep you accountable to it.

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Thanks for the question, Waiting for the Light, and congratulations on how far you have come in your business. There is always more work to be done. Your to-do list will never be finished. There will always be one more email to write, one more spreadsheet to pour over, one more prototype to tinker with.

The light at the end of the tunnel will keep moving further away, and that is exciting! It means you are moving forward.

What you can do now is establish boundaries around your time so you can make space, slow down, and celebrate when you hit the different markers along that tunnel.

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Book a free consultation with me if you need help working through any of these steps!

Ask AshleyProductivity
Ashley Janssen

Ashley Janssen

Productivity consultant, writer, speaker, serial entrepreneur, chaos calmer, introvert, cat-lady. Lover of books, fitness, old fashioned’s, basketball, and video games.

Follow me on Twitter, and LinkedIn.


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